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Holiday Rentals in Islamorada, FL

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    All 114 Rentals in Islamorada
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    Travellers to Islamorada are booking December dates now. Secure your holiday rental today, and have the perfect trip.
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    1 / 10
    5 of 5 stars (1) Excellent
    3 Bedrooms / 1 Bathroom / Sleeps 6
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    $5,719
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    1 / 1
    4.5 of 5 stars (4) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    1 / 35
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Private Outdoor...
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
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    • Elder access
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 17 November 2014
    my husband and 2 friends stayed in this unit for 4 days and 3 nights. they found the condo to be clean, plenty of space and conveniently located. they would definitely stay...
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    $349
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    1 / 29
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • x
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    About this property
    Thank you for considering Our home in the Florida Keys!... Our slice of Paradise! Stay at a Luxury Townhome at Executive Bay Club (Islamorada , Florida ) The Executive Bay Club is located in Islamorada which is best known for it's crystal blue water where you can enjoy sport fishing, snorkeling,... View all property information
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    Islamorada, Florida Keys 33036
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    $227
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    1 / 5
    1 Bedroom / 2 Bathrooms / Sleeps 2
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    • Wi-Fi
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
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    • ?
    • ?
    About this property
    Malaysian room is poolside in a tropical atmosphere facing a beautiful waterfall. Features a mini kitchen with blender, coffee maker, microwave, refrigerator and toaster oven. A/C, heat, TV and WiFi. Includes a full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO... View all property information
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    Islamorada, Florida Keys 33036
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    $15,250
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    1 / 12
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
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    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Oasis. Oasis is located at Mile Marker 75.6, in beautiful Islamorada. This Beautiful three bedroom, three bath home will sleep 8 people very Comfortably. Besides the... View all property information
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    Islamorada, Florida Keys 33036
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    $159
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    1 / 22
    4 of 5 stars (6) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
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    • Elder access
    About this property
    Located in beautiful Plantation Key, the first Island of Islamorada. An area of all waterfront homes Wifi, boat dock, trailer parking, and all amenities are included also, Lovely Tiki Hut overlooking the water. Plus a huge covered entertainment area complete with dining areas, settee and gas... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 31 March 2015
    Cozy, clean, nicely appointed apartment with a gorgeous canal to the bay right outside the door. The owners are warm, friendly, and have thought of every convenience. Wonderful...
    5 of 5 stars Reviewed 30 March 2015
    This was exactly what we were looking for. Pam and Charlie are wonderful hosts. Charlie gave us some insider tracks on fresh seafood and favorite local restaurants. The rental...
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    $5,909
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Private Fishing...
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Provisionally not available February through April, 2016. I will notify all who inquire if it becomes available. Available: September/October: $4600 November/December/January: $4900 single month, two or more months $4800 KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef,... View all property information
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    Islamorada, Florida Keys 33036
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    $635
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    1 / 22
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    **We do not use the optional calendar feature on this listing. ** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not receive a reply, please contact me again! Email me for additional pictures of this wonderful... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 23 April 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
    5 of 5 stars Reviewed 14 April 2015
    We had a wonderful time at this waterfront paradise. Waking up in the morning to a beautiful view of the waterway outside the window of our bedroom. Not to mention enjoying the...
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    $22,874
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Latitude: Freedom of thought or action. No word could better described this Keys Vacation Home. Embrace the serenity of the azure Atlantic Ocean while you relax in the private heated pool. Latitude boasts 2 master suits and... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 17 June 2013
    Our extended family of 8 had a wonderful week at Latitude. The house is modern and immaculate. There was plenty of space and privacy for everyone. We had a great time watching...
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    $1,906
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    1 / 36
    4 of 5 stars (16) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 12 January 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    $328
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    1 / 21
    5 of 5 stars (3) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Gym
    • Hot Tub
    • Internet Access
    • Safe
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Escape to Islamorada in the Florida Keys and enjoy the breathtaking gulf and ocean views from your top floor balcony in this decorator furnished, two bedroom luxurious condo. This unit located in the complex of Bay Harbour offers a private 50' boat slip, heated swimming pool, hot tub, club... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 8 February 2015
    This condo has more than you would expect in a condo. It has every utensil, cookware, storage containers appliances both small and large you could ever need. Unlike most condo...
    5 of 5 stars Reviewed 3 September 2014
    Looked far and wide for a place in the keys that was on one level for my mom that uses a walker. Finally found the one! The owner is very helpful and communicative and worked...
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    $454
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    1 / 24
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Venetian Shores 3/3 home with deep water boat slip, gorgeous custom pool with integrated hot tub and built-in seating. This beautifully updated tri-level home offers a 2/2 upstairs with soaring ceilings, wood floors and a wide porch off the living room overlooking the pool and a wide turn in the... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 25 March 2015
    Lovely Home, very spacious, clean, everything you need..... the Owners had. We even saw a Mother Manatee with their baby swimming upto our boat slip in the back. This was our...
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    $6,354
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Sauna
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass... View all property information
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    Islamorada, Florida Keys 33036
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    $7,625
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    1 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveller have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 19 November 2014
    We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
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    1 / 11
    5 of 5 stars (4) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
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    About this property
    Millionaire's Row! Beautiful home with private heated swimming pool directly on the ocean in Islamorada. This home offers excellent views of the ocean from many rooms. 5 bedroom, 4 bath owners home is beautifully furnished with ocean views from patio, living room (upper and lower), and dining room... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    $1,048
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    1 / 30
    5 of 5 stars (18) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (18) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Get away from it all in our tranquil waterfront condo at Summer Sea in beautiful Islamorada. Fully equipped, with newly updated kitchen and bathroom, flat screen television, and stunning views of Florida Bay from our patio. Located right in the heart of all the Keys has to offer - beautiful... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 1 May 2015
    I always take descriptions with a grain of salt and assume that the photo's are taken with the best possible light.. So I was expecting a decent place with a decent view at best...
    5 of 5 stars Reviewed 22 April 2015
    The apartment is well appointed with comfortable furniture and plenty of crockery and cutlery. The building is quiet and the view from the balcony over the pool and dock out to...
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    $3,523
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    1 / 29
    5 of 5 stars (7) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
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    • Wheelchair access
    • Elder access
    • ?
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    About this property
    Beautiful three bedroom bay side townhouse with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 27 October 2014
    We never did a vacation rental before and it was Great. Place had everything we needed and had enough space for our large group! It was also clean. Pool was big and nice! we...
    5 of 5 stars Reviewed 19 July 2014
    Would suggest having map of condo development for first time visitors. If items were missing or needing repair, received excellent response time. Patio chairs need replacing...
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    $227
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    1 / 25
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 7 NIGHTS, SATURDAY TO SATURDAY RENTAL ONLY BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Location Information
    Islamorada, Florida Keys
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    $1,398
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    This magnificent two bedroom, two bath Condo, sleeps six comfortably. Newly decorated & tastefully furnished with wood floors throughout. Fully-equipped kitchen with new appliances. Flat Screen TV with Digital sound, DVD, stereo and CD player. WIFI included !!! Outside patio and laundry just steps... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 7 January 2014
    I traveled with my partner and another couple. We enjoyed the comfortable roomy accomodations. Loved the convenience of cooking meals. The grounds are beautiful. We enjoyed the...
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    $381
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (22) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    House, 2 Bedrooms + Convertible Bed(s), 2.5 Baths (Sleeps 5) Islamorada home set in OceanFront gated community with swimming pool and private boat dock This charming home has 2 Bedrooms, 2.5 Bathrooms, A/C, Granite work tops, modern stainless steel appliances. Open porches and balconies, rich... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 21 August 2014
    We fell in love with the villa the minute we walked in through the door. Everything was immaculate and extremely welcoming. The owner had thought about everything and the box of...
    5 of 5 stars Reviewed 30 June 2014
    This was the perfect place for a relaxing vacation with my extended family. The location was great, and close to all Islamorada has to offer. The pool was so nice, overlooking the...
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    $1,017
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    1 / 30
    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Escape to paradise in the fabulous Florida Keys at Futura Yacht Club. This rental property is a private gated community with a 65 slip deep water marina. This tropical waterfront community offers world class fishing and diving, 2 lighted tennis courts, heated pool, private beach, basketball and... View all property information
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    Islamorada, Florida Keys 33070
    3 of 5 stars Reviewed 5 March 2014
    This was a nice rental. There seems to have been a nice soft update done not to long ago, and it appeared that some features were still being upgraded. The building is clean...
    5 of 5 stars Reviewed 14 January 2012
    The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
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    $216
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Welcome to Sol Y Mar SOL Y MAR is 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. Property is located in Tavernier, in Islamorada, Florida (MM90). The Center of the Keys, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 26 April 2015
    Our family of 5 adults spent a week at Sol Y Mar in Tavernier Florida. We were fortunate to have Nestor Loredo as our agent. The house was all as promised. Nestor met us the and...
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    $2,224
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    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveller have booked this property
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    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Enjoy the most beautiful sunsets on earth from this gorgeous 4bedroom,5bathroom tropical paradise. Comes complete with Bayfront pool and lounge area that will leave you breathless. Pool table, cabana, outdoor kitchen, snorkel in the backyard!!!! Seven Flat Screens and entire house wired for sound.... View all property information
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    Islamorada, Florida Keys 33036
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    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    traveller have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Ocean Views
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    BEAUTIFUL NEWLY REMODELED 3 BEDROOM, 2 FULL BATHROOM VACATION RENTAL IS LOCATED IN THE EXECUTIVE BAY CLUB. BREATHTAKING BAY VIEW FROM YOUR OWN BACK YARD! UNIT HAS BRAND NEW CUTOME KITCHEN CABINETS WITH GRANITE COUNTER TOPS. ALL STAINLESS STEEL APPLIANCES, DOUBLE DOOR REFRIGERATOR, DISHWASHER,... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 25 April 2015
    We really enjoyed our stay here. We stayed with my husband and I and 3 kids ages 8,6 and 2. It was perfect. We spent a lot of time at the pool which was about 20 steps from the...
    5 of 5 stars Reviewed 24 February 2015
    The place was beautifully decorated and in excellent condition. From the patio you had an excellent ocean view that was a short walk to a small beach. My teens has a blast and...
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    4.5 of 5 stars (11) Very good
    2 Bedrooms / 1 Bathroom / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Escape from the world in this beautiful island paradise.Plenty of room to spread out in a two bedroom condo. Relax by the heated pool overlooking the turqoise bay; fish from the dock, snorkel in the protected cove. Kids can play in the game room or playground. Enjoy the clear, turquoise waters,... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 10 July 2014
    Stayed here the last week in June with my wife, two kids and granddaughter. Room was clean and well laid out but a little bit cramped for the number of people. Closet space was...
    5 of 5 stars Reviewed 27 May 2014
    The condo was nicer and larger than we expected. It had everything we needed plus a few surprises: beach chairs and a float, very comfortable beds, and quiet neighbors. Also...
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    5 of 5 stars (3) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    travellers have booked this property
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Vacation in Paradise!!... you will love this fun filled, relaxing townhouse in the beautiful Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing Capital of the World. It is a private, gated community and the grounds have 2 tennis courts, a swimming pool, a clubhouse, a... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 13 April 2015
    The owners were amazing to work with and very quick to answer any questions. The condo was beautiful and very well stocked with anything you would need for a vacation in the Keys...
    5 of 5 stars Reviewed 7 March 2015
    The Daniels unit in Executive Bay Club is great. Very clean and modern up to date. People were very friendly and helpful nice events in clubhouse. Large rooms upstairs and...
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    1 / 29
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 12 May 2014
    We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
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    $593
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    6 Bedrooms / 3 Bathrooms / Sleeps 12
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    • Air Conditioning
    • Balcony
    • Fireplace
    • Internet Access
    • Private Outdoor...
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    This is a 6 bedroom pool home with direct dockage just off Snake Creek. Home has 2 kings, 3 queens, and 2 twins. Located at mile marker 86 on the bay side Beds: 2 King Beds, 2 Queen Beds, 1 Double Bed, 2 Twin Beds View all property information
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    Location Information
    Islamorada, Florida Keys 33036
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    1 / 49
    5 of 5 stars (6) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    FOR ADDITIONAL REVIEWS GO TO 'HOMEAWAY.COM' LISTING #341722 TO AVOID SCAM WE URGE YOU TO PLEASE CONTACT OWNER BY PHONE BEFORE FINALIZING ANY ARRANGEMENTS IF YOU GET A RESPONSE FROM BESTHOLIDAYRENTALS.COM **** IGNORE IT **** SCAM MINIMUM STAY 7 NIGHTS, MAXIMUM OCCUPANCY 6 PPL, RENTAL PATTERN... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 14 May 2014
    We had such a wonderful time at Paradise Point!! The views were beautiful!!! The kids loved the pool and all the sealife we saw. Many fish and stingrays, just to name a few...
    5 of 5 stars Reviewed 14 February 2014
    My week started when my wife and I along with our two friends met Juan Sanchez at this home he calls Paradise (which it really is). The man from my first e mail to him to locking...
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    5 of 5 stars (6) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 16
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This is an exclusive oceanfront private gated estate home with 200 feet of oceanfront on two acres. This property also features 200 feet of dock, Boat lift, Tiki hut on private beach, Heated pool and Wireless remote Internet. Southern Diversion has just been completely renovated. Brand new... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 29 March 2015
    I did not stay here but our friends did and we attended a wedding there and it was amazing. Beautiful place and very clean. I hope my kids get married there!
    5 of 5 stars Reviewed 29 March 2015
    We spent one week in this beautiful an perfect home. Everything was great, the location, the accommodations and the service. We will bring the family again and we highly recommend...
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    $3,113
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Balcony
    • Dryer
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Revel in the beauty of the morning sunrise as you relax on your own, private lanai while sipping your morning coffee, or enjoy a meal al fresco to the sound of the waves and gulls. This piece of paradise is sure to become your favorite home away from home. This beautifully furnished and spacious... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 26 March 2015
    Great property! Very beautifully decorated. I loved the view, really enjoyed my stay! I look forward to staying there again soon!
    5 of 5 stars Reviewed 20 January 2015
    This condo is beautifully decorated and chock full of everything you need to make your stay just perfect. The condo and the complex are extremely well maintained and have the...
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    $1,017
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    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    * 7 Day Rental minimum - Saturday to Saturday * Please check the calendar prior to inquiry Sleeps 8 adults plus up to 4 children under 6 allowed (fire code regs)... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,526
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    This property is a single family home with a boat dock included in the price. Not a condo. Note: we only offer 7 day minimum stays with 4PM Saturday check ins and 10 AM checkouts. Maximum number of guests is 5. No pets, No smoking and maximum guests is strictly enforced. Rates start at $2,775... View all property information
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    Islamorada, Florida Keys 33036
    From
    $22,874
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    1 / 1
    4 of 5 stars (1) Very good
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Casa Dorado is a premier rental vacation home on Lower Matecumbe Key in Islamorada, Florida. Completely renovated in 2014, the spacious living and dining areas, four bedrooms, and three and a half bathrooms will make for a very comfortable stay during your visit to the Florida Keys. The house is... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 27 December 2014
    The house is newly remodeled and in great condition. Very clean- which was a must for me! The views are wonderful. We thouroghly enjoyed the week we spent there (myself, my...
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    1 / 27
    4 of 5 stars (6) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Modern canal home with views of Snake Creek. The property is completely fenced in. Third level master suite with private master balcony. Well furnished with all the extras. Easy ocean or bay access and dockage up to 50 feet. Open floor plan with regulation pool table and screened in porch. This... View all property information
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    Islamorada, Florida Keys 33036
    From
    $2,542
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    1 / 24
    4.5 of 5 stars (6) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    Amenities & Details
    • Dishwasher
    • Grill
    • Internet Access
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Enjoy this Bayfront home with a spectacular sunset view, fenced yard and tile throughout the house. Also has great dockage and clean swimming area. Secured wi-fi, local telephone, & cable television (basic) included. VACATION RENTAL LICENSE: VR-039 CLICK HERE to view photos on a mobile device.... View all property information
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    Islamorada, Florida Keys 33036
    From
    $635
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    1 / 38
    5 of 5 stars (23) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (23) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Private heated pool vacation home located on deep canal with immediate access to ocean and bay. Mile Marker 86 in prestigious Venetian Shores. Pet friendly Vacation Rental License. No VR-001 106 San Remo Drive, Islamorada, Florida, 33036 Please email VenetianTropics@aol.com for the application.... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 24 March 2015
    The home is luxurious. It has all the amenities needed for a trip to the Keys. This is the third time I have rented the home and there have been some nice improvements made to the...
    5 of 5 stars Reviewed 19 May 2013
    This home was the perfect location for our spring break vacation. It was so central to many activities on the keys and so many wonderful restaurants. The home is very nice, a...
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    $318
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Balcony
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Welcome to beautiful Islamorada located in the Florida Keys. Islamorada is known as the 'Sport Fishing Capital of the World'. Our ocean contains the world's most sought-after gamefish including tuna, dolphin, Marlin, permit, tarpon and bonefish. In addition to fishing, Islamorada is a favorite of... View all property information
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    Islamorada, Florida Keys 33070
    From
    $2,097
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    1 / 5
    4.5 of 5 stars (2) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Hot Tub
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Plantation Key canal home. Nice new home with screened porch and pool table! Delightfully furnished for a comfortable stay. Excellent outdoor entertaining space, great for soaking in the hot tub, gazing at fish in the canal, having cocktails under the Chickee, or for the kids to run around and... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 12 August 2013
    We completely enjoyed our stay. Plenty of room for 6 ppl to sleep. Nice sized kitchen and dining area. We stayed with two young children and they loved it. Great location for both...
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    $5,719
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    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    Village Permit #VR-09-82 You can not rent this property for less than one week. Ahhhh...Ocean Front...Pool...Dockage...It's all hear at Aguazul. Aguazul is located at Mile Marker 89, in beautiful Islamorada. This gorgeous four bedroom,three bath home will sleep 8 people very comfortably. Aguazul... View all property information
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    Islamorada, Florida Keys 33036
    From
    $7,625
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    1 / 1
    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A quaint bungalow on a not-so-quaint piece of oceanfront land right in the Heart of Islamorada! This home has two bedrooms, two bathrooms, and a lot of Keysy charm. During your stay, you will enjoy such amenities as a fishing dock with Chickee hut (1ft draft), cable television, a kayak, and a white... View all property information
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    Islamorada, Florida Keys 33036
    From
    $1,684
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Please send us an inquiry or call us for availability. We have condos and townhomes. Prices vary on the units. Your own tropical paradise overlooking the fabulous Florida Bay in Islamorada. Futura Yacht Club is a 70 unit community with a 53 slip marina and accommodations available for that... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $178
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    3 of 5 stars (1) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
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    • Air Conditioning
    • Balcony
    • Dishwasher
    • Gym
    • Ocean Views
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want... View all property information
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    Islamorada, Florida Keys 33070
    3 of 5 stars Reviewed 12 April 2015
    I spent a week at Sea Gulls with my 18 year old daughter. The unit was well equipped and clean. The pool and tennis courts were nice. The view was adequate. To the left, a...
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    $1,271
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    4.5 of 5 stars (3) Very good
    2 Bedrooms / Sleeps 4
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Gym
    • Internet Access
    • Sauna
    • Shared Outdoor Pool...
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Please send us an inquiry or call us for availability. Prices vary on the units. Sea Gulls Condominiums, on the shores of the Atlantic Ocean provides vacationers the splendor of the Atlantic waters with luxury living at an affordable price. This perfect family vacation destination offers something... View all property information
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    Islamorada, Florida Keys 33036
    From
    $254
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    1 / 13
    5 of 5 stars (26) Excellent
    Studio / 1 Bathroom / Sleeps 2
    Overview Reviews (26) Make Enquiry
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    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Private Fishing...
    • Satellite TV
    • Washer
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • x
    • Wheelchair access
    • Elder access
    • x
    About this property
    PLEASE DO NOT TRY TO BOOK THROUGH FLIPKEY! Booking instructions will be provided when you send your inquiry, saving you a significant amount in FlipKey booking fees. We do not use the optional calendar feature on this listing. We are fully booked until May 30th! This is a very popular rental, so... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed 17 April 2015
    Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips...
    4 of 5 stars Reviewed 20 January 2015
    Great place for a couples private getaway. Host's are very pleasant & leave you to yourselves, but are there if you need anything. No stove, you have to use a microwave/convection...
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    $4,194
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    1 / 1
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
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    • Air Conditioning
    • Dishwasher
    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This three bedroom, three bathroom condominium sits on a lushly landscaped property, offering the Florida Keys you've always imagined. Enjoy beautiful oceanfront vistas from one of two balconies. Take a dip in the spacious pool that sits right at the foot of the condo staircase. Or journey a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,735
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    1 / 50
    4 of 5 stars (17) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 10
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    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Waterfront
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This oceanfront home will surely get you in a Keys state of mind. Featuring five bedrooms, a pool, and an expansive private beach, its ideal for anything from a reunion of extended family or friends, to a small wedding, to a relaxing family vacation. The 4,300 square foot house will capture your... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed 6 March 2015
    We traveled to Islamorada during late January-early February. This house was lovely and had been recently undated. The staff who took care of the house were nice and immediately...
    2 of 5 stars Reviewed 29 April 2014
    Everything seemed to be broken. The pool water had a green tint and was finally shocked by the pool guy. One of the closet doors was broken off and placed in the closet. One of...
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    3 of 5 stars (3) Average
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Satellite TV
    • Sauna
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    Complex Amenities - MM 88.5 - Building has five floors - Large swimming pool & children's pool - Exercise room with sauna - Laundry room on each floor - Billiard and Ping-Pong room - Adult party lounge - Cookout facilities - Direct access to Florida Bay and then ocean - Minutes from Islamorada,... View all property information
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    Location Information
    Islamorada, Florida Keys 34747
    2 of 5 stars Reviewed 22 August 2013
    In addition to my wife's comments there is another thing a prospective renter must take into consideration: the lease agreement states that any disputes with the rental agent be...
    2 of 5 stars Reviewed 13 August 2013
    My husband and I recently rented this condo for a 3-night dive trip with our 2 boys, ages 17 and 19. While the condo itself was clean, the building was old and the parking lot was...
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