We noticed that you're using an unsupported browser. The TripAdvisor website may not display properly.
We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Holiday Rentals in Islamorada, FL

Map
Satellite
Map updates are paused. Zoom in to see updated info.
Reset zoom
Updating Map...
Your filters are still active.
There are no pins in your viewport. Try moving the map or changing your filters.
dd/mm/yyyy dd/mm/yyyy
    There are no pins in your viewport. Try moving the map or changing your filters.
    • {providername} {price}
    {providername} {price}
      {listitems}
    {sold_out_text}
    We can't find prices for this accommodation
    From {rate_price} {rate_periodicity}
    Payment Protection
    Use a credit card to book with our Peace of Mind Protection.Learn more
    Find a rental
    Price per night
    Min
    to
    Max
    Bedrooms
    Any
    Amenities
    Select
    Community
    Select
    Payment
    Select
    Go to map view
    More filters
    All 114 Rentals in Islamorada
    loading...
    Sort by
    From
    $1,704
    / Week
    View Details
    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / Sleeps 4
    Overview Reviews (1) Make Enquiry
    From
    $2,958
    / Week
    View Details
    1 / 27
    4 of 5 stars (6) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Enquiry
    From
    $15,431
    / Week
    View Details
    1 / 1
    5 of 5 stars (13) Excellent
    10 Bedrooms / 8 Bathrooms / Sleeps 20
    Overview Reviews (13) Make Enquiry
    From
    $5,787
    / Week
    View Details
    1 / 13
    4 of 5 stars (1) Very good
    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
    • ?
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,568
    / Week
    Payment Protection
    View Details
    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Enquiry
    Amenities & Details
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,122
    / Week
    View Details
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $7,715
    / Month
    View Details
    1 / 1
    5 of 5 stars (2) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) 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
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,815
    / Week
    View Details
    1 / 50
    4 of 5 stars (17) Very good
    5 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (17) Make Enquiry
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,958
    / Week
    View Details
    1 / 30
    4.5 of 5 stars (7) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (7) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Beautiful designer appointed Oceanside canal home located at the Mile Marker 76.5 in Lower Matecumbe (South part of Islamorada). This home is the second one in on a point and has a great ocean view. Fully loaded kitchen with dishwasher, microwave, coffee maker, toaster, and blender. There are two... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,430
    / Month
    Payment Protection
    View Details
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    List your property for free!
    List your holiday rental where TripAdvisor travellers can find it.
    Add a Listing
    From
    $257
    / Night
    View Details
    1 / 13
    5 of 5 stars (26) Excellent
    Studio / 1 Bathroom / Sleeps 2
    Overview Reviews (26) Make Enquiry
    Amenities & Details
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,929
    / Week
    View Details
    1 / 13
    4.5 of 5 stars (16) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (16) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Waterfront
    • Water Views
    • Wi-Fi
    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 a couple of units. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool, sandy beachy area, and fishing pier with flats boat dockage (drawing 24' or less) located directly on the ocean.... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $891
    / Week
    View Details
    1 / 29
    5 of 5 stars (2) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (2) 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
    • ?
    • ?
    About this property
    Beautiful two bedroom townhouse on the Bay side with private beach access in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise! Come and relax at our beautiful, newly renovated townhome in the Florida Keys. The Executive Bay Club is located in Islamorada, the Sport Fishing... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $1,935
    / Week
    View Details
    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 7
    Overview Reviews (2) 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
    • ?
    • ?
    About this property
    Water Front home, located Oceanside in Lower Matecumbe key, Islamorada mile marker 73, (The Sport Fishing Capital of the World). 15' wood dock and 12’ wide ramp, so bring your own boat and enjoy the sun!! Easy canal access to the ocean. Maximum boat size is 27'. Only 1 boat allowed. There is a... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,250
    / Night
    Payment Protection
    View Details
    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $180
    / Night
    Payment Protection
    View Details
    1 / 11
    3 of 5 stars (1) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
    travellers have booked this property
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    From
    $3,858
    / Month
    View Details
    1 / 11
    3.5 of 5 stars (2) Average
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Grill
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Modest home in great subdivision. Excellent, deep dockage on a wide canal with easy ocean and bay access via Snake Creek. Cool tropical breezes can be enjoyed on the screened in porch. Minimum Stay for this home is 28 night minimum. Wirelss internet. Click Here for Map! CLICK HERE to view photos... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,430
    / Week
    View Details
    1 / 8
    3 of 5 stars (1) Average
    3 Bedrooms / 4 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Internet Access
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • ?
    • ?
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    VR-203 You can not rent this property for less than one week. Relax and rejuvenate at The Palms. Features are a plantation-style home and beautiful wrap around porch, 3 bedrooms/3.5 baths, a beach entry pool, and abundant coquina decking. The natural landscaping enhances the amazing grounds and... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33063
    From
    $3,858
    / Month
    View Details
    1 / 23
    3.5 of 5 stars (2) Average
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (2) 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
    This 2Bed/2Bath stilt home is located at mile marker 89 at the very end of Indian Waterways subdivision. Located on a canal with approximately 30' of dockage, you'll have almost immediate access to the Florida Bay and just a 7 minute boat ride to Tavernier Creek, which takes right over to the... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $321
    / Night
    Payment Protection
    View Details
    1 / 20
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    Get the List
    From
    $238
    / Night
    View Details
    1 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Gym
    • Satellite TV
    • Shared Outdoor Pool...
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    About this property
    If you’ve been to Islamorada you know it as the sportfishing capital of the world, a place where you’ll find every water-related activity imaginable, with fine restaurants to crab shacks serving local fare, and plenty of nightlife for both the young and young at heart. If you’ve never been here, a... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    From
    $1,286
    / Week
    Payment Protection
    View Details
    1 / 9
    2 Bedrooms / 4 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Ocean Views
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • Wheelchair access
    • Elder access
    About this property
    This oceanfront condo in Islamorada Florida (Keys) is located at mile marker 90. It is the best ocean view from everyroom and is on the 4th floor. IT IS A ONE WEEK MINIMUM AND 4 PERSON MAXIMUM BY LICENSE. ..It has all tiled floors, newly painted, new AC, and has all the conveniences of home.... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    From
    $193
    / Night
    View Details
    1 / 12
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    About this property
    Welcome to our beautiful, private and secure gated community with all of the amenities to make your vacation as relaxing or exciting as you wish. Located on Plantation Key in Islamorada at mile marker 88.5 on the bay side and boasting a great 60 slip marina, it provides quick access to the ocean... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $11,509
    / Week
    View Details
    1 / 13
    5 Bedrooms / 7 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    About this property
    You can not rent this property for less than one week. The ultimate island experience awaits you at Kara-Pan I. This exquisite, private, two story, Plantation Style home is located on a pristine natural white sand beach with oceanviews that inspire relaxation. The 5 bedroom 7 bath home with a wrap... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $296
    / Night
    View Details
    1 / 15
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview 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
    Special vacation rental rates for off-season bookings and also for some last minute dates! Call us now for details. Located in Islamorada the fishing capitol of the world, this is a beautiful home decorated with Island style decor. Over 3,000 square feet of living space. 100' of dock, less than two... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $9,644
    / Month
    View Details
    1 / 9
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview 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
    Please contact us if you have any policy questions since we do not agree with this website forcing us to choose policies they dictate. We have our own polices so please ignore what's posted in the policies section on this website. Also please visit our website at www.KeysRentalHouse.com Beautiful... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $230
    / Night
    Payment Protection
    View Details
    1 / 5
    1 Bedroom / 2 Bathrooms / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,858
    / Month
    View Details
    1 / 1
    2 Bedrooms / 1 Bathroom / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Satellite TV
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    'Cute & Keysy' perfectly describe this Conch home! Located in the Tollgate Shores subdivision of Lower Matecumbe (south Islamorada), this delightfully quaint home has lots of character, charm, and is well-maintained. You'll enjoy sea breezes and the smell of salty air coming through the windows of... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,829
    / Week
    View Details
    1 / 1
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Add some Caribbean spice to your next visit to the Florida Keys. This two-bedroom/two-and-half bath villa sits within Angler's Reef, a charming community of detached town homes that take their inspiration from the architecture of the British West Indies. Located at mile marker 85, on Windley Key,... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    Enquire for rates
    1 / 8
    4 of 5 stars (2) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (2) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Hot Tub
    • 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 pretty, four-bedroom, three-bath house is conveniently located in the heart of Islamorada, the fishing capital of the world. Situated in a pretty upscale neighborhood of all waterfront homes, the house is equipped with all the comforts of home. It is additional tidy and modernly furnished.... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $698
    / Night
    View Details
    1 / 16
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview 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
    Ocean front retreat with overwhelming views of the Atlantic, large open verandahs, 100 feet of very private white sandy beach, and a gated entrance. The beach is very private on 3/4 of an acre loaded with palm trees. You can snorkel in the backyard on coral reefs within 1000 feet of the shore. Use... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $230
    / Night
    View Details
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $230
    / Night
    Payment Protection
    View Details
    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Grill
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • x
    • x
    About this property
    Enter through a private garden with a tropical atmosphere to a quiet and secluded room with a queen size bed and a private bath. The room is completely private and features a coffee maker, microwave, refrigerator, TV and free WiFi. Full breakfast. LOCATED IN A QUIET,SECLUDED , TROPICAL SETTING... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33136
    From
    $4,501
    / Month
    View Details
    1 / 1
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Grill
    • Internet Access
    • Satellite TV
    • Waterfront
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    Looking for an extended stay in the Upper Keys that won't bust the bank? If so, you need not search any farther than this cozy, modern home on Islamorada's Plantation Key. Located in the popular Indian Waterways neighborhood, this three-bedroom/two-bath house is a great value at just $3,500 per... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    Enquire for rates
    1 / 47
    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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 34747
    From
    $120
    / Night
    View Details
    1 / 16
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Balcony
    • Dishwasher
    • Dryer
    • Grill
    • Satellite TV
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Vacation in beautiful peaceful Islamorada, in the Florida Keys. Islamorada, 'Fishing Capital of the World'. Bayside access Townhouse is a newly redone 2 bedroom, loft, 1 1/2 bath, comfortably sleeps 6 adults, patio with BBQ. Fully furnished and kitchen totally equipped. Washer/Dryer, Flat screen... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $459
    / Night
    View Details
    1 / 8
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Internet Access
    • Private Outdoor...
    • Satellite TV
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    Oceanfront splendor on the Atlantic ocean. Has a 350' pier that can accomodate most any size boat. Just relax by the pool on those hot days or take a dip in the ocean. The pool is heated for the winter months. The house is extremely private. There is a wooden fence around the house and... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    From
    $166
    / Night
    Payment Protection
    View Details
    1 / 9
    1 Bedroom / 1 Bathroom / Sleeps 2
    traveller have booked this property
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Internet Access
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This wonderful room opens up into a garden with a water pond. It includes a/c, coffee maker, TV, free WiFi, heat, microwave, refrigerator, shared bath with one other couple. Pool on premises. Close proximity to the beach. Includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $114
    / Night
    Payment Protection
    View Details
    1 / 7
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Grill
    • Housekeeping...
    • Internet Access
    • Shared Outdoor Pool...
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    A small stand alone room in the corner of the garden. Features a/c, coffee maker, free WiFi, grill on premises, heat, microwave, refrigerator, shared bathroom with one other couple, TV and includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET MINUTES TO FISHING, DIVING,... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $4,115
    / Month
    View Details
    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview 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
    • ?
    • ?
    About this property
    This charming 2 bedroom and 2 bathroom home is located at the 90 mile marker. This home is centrally located to shopping, restaurants, and grocery store. This home offers deep water dockage and easy access to the Atlantic Ocean via Tavernier Creek. Great outdoor space whether you are sitting on... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,215
    / Month
    View Details
    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Internet Access
    • Washer
    • Waterfront
    • Water Views
    • Wi-Fi
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    This delightful 2 bedroom, 2 bathroom home is located in Port Antigua (south Islamorada) at the 74 mile marker. While not located directly on the bay, you'll still be able enjoy the homeowners park that has a beach and beautiful sunsets. The home comes equipped with Wi-Fi internet. Click here to... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $459
    / Night
    View Details
    1 / 24
    2 Bedrooms / 2 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
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    ower Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. The units are available for rent by the week, or month. Each unit sleeps up to 6 people - rent one or all... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $487
    / Night
    View Details
    1 / 14
    1 Bedroom / 2 Bathrooms / Sleeps 4
    Overview 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
    MINIMUM RENTAL 1 MONTH: Everything in this unit is exquisite - furnishings, linens, updated kitchen, appliances, and bathrooms. Great views of Florida Bay and our fabulous Keys sunsets. This complex is conveniently located just steps from a full service marina and 2 highly acclaimed restaurants.... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $6,430
    / Week
    View Details
    1 / 38
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Dishwasher
    • Dryer
    • Fireplace
    • Grill
    • Hot Tub
    • Internet Access
    • Private Outdoor...
    • Washer
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    OSPREY BAY VILLA! Wonderful bayfront home in the heart of Islamorada in the fabulous Florida Keys for rent by the week or monthly. Offering 5 bedrooms and 3 full baths on 2 living levels overlooking the Florida Bay with its incredible sunset views. Sleeps 10 people comfortably. Spacious fully... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $129
    / Night
    View Details
    1 / 6
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview 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
    Call Property Manager for Best Rate. Located on Windley Key this gated 5 unit complex has the best of the Keys with a private pool sandy Beachfront, fishing pier with flats boat dockage (drawing 24' or less) located directly on the ocean your views could NOT be any better. Under the condo... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $219
    / Night
    View Details
    1 / 26
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview 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
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33070
    From
    $5,787
    / Month
    View Details
    1 / 33
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    From
    $172
    / Night
    View Details
    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY 1 MONTH: This 4th floor end unit in one of Key Largo's finest bay front condominium complexes offers a beautiful view of the Florida Bay and lots of natural light. You'll love the updated kitchen with granite counters, new cabinetry and appliances. New linens and fresh paint add to... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys
    From
    $5,787
    / Week
    View Details
    1 / 36
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dishwasher
    • Dryer
    • Grill
    • Internet Access
    • Private Outdoor...
    • Washer
    • Water Views
    Suitability
    • Pets allowed
    • Smoking allowed
    • Suitable for children
    • x
    • x
    • ?
    • Wheelchair access
    • Elder access
    • ?
    • ?
    About this property
    How about sipping coffee and watching the sun come up as you fish off the end of your very own 300 foot pier? Sounds good, right? Well, that's just one reason to stage your upcoming vacation at this lovely, hacienda-style home on a quaint and private oceanfront street in Islamorada. CLICK HERE to... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys 33036
    From
    $459
    / Night
    View Details
    1 / 22
    3 Bedrooms / 2 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
    Upper Duplex - This is one of three rental units on this fabulous property. The Little Bay property is a one acre lush tropical setting in a gated compound located directly on Florida Bay. This is one of 3 separate units for rent by the week or month. Each unit sleeps up to 6 people - rent one... View all property information
    Make Enquiry
    Location Information
    Islamorada, Florida Keys