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Pet Friendly Holiday Rentals in Islamorada, FL

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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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    From
    $177
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
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    $686
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    1 / 38
    5 of 5 stars (23) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    $314
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    1 Bedroom / 1 Bathroom / Sleeps 3
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    $2,400
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    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Internet Access
    • Private Fishing...
    • Private Outdoor...
    • DVD Player
    • Water Views
    • Air Conditioning
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    $1,097
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Enquiry
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    • Private Outdoor...
    • Internet Access
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Islamorada, Florida Keys 33036
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    $686
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    1 / 21
    5 of 5 stars (3) Excellent
    4 Bedrooms / 4 Bathrooms / Sleeps 10
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Hot Tub
    • Water Views
    • DVD Player
    • Stereo System
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    WWW.SCHOONERHAMMOCK.COM This unique property offers : -master suite -apartment -cottage -3 full kitchens On Atlantic Ocean. Simple, sweet, and serene sanctuary. Please contact Andy Cancela 828 808 1693 We love The Lord and look forward to sharing our home with you. View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed 14 January 2015
    Growing up in South Florida and the Keys but now moved farm away, I wanted to show my husband and young children the Florida I remembered as a child. This my friends was more than...
    5 of 5 stars Reviewed 24 October 2014
    My family/extended family stayed here in June 2012 for two weeks and it was beyond wonderful. The owner ALWAYS was quick to respond to emails even if it was to say "you're...
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    From
    $245
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    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveller have booked this property
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    • Air Conditioning
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Housekeeping...
    • DVD Player
    • Stereo System
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • 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
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    Islamorada, Florida Keys 33036
    From
    $191
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
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    Amenities & Details
    • Grill
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • ?
    • 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 YET... View all property information
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    Location Information
    Islamorada, Florida Keys 33136
    From
    $122
    / Night
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    1 / 7
    1 Bedroom / 1 Bathroom / Sleeps 2
    travellers have booked this property
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Stereo System
    • Housekeeping...
    • Air Conditioning
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Wi-Fi
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • 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
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,360
    / Week
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Shared Outdoor Pool...
    • Washer
    • Water Views
    • Hot Tub
    • Wi-Fi
    • Satellite TV
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    From
    $6,857
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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Dryer
    • DVD Player
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Spacious 3/3 canal front home in Lower Matecumbe. 75 Ft of dock with 45 FT cut-in for extra boat protection. Walk down the street to world famous Robbies for dinner/drinks and boat, kayak and jet-ski rentals. Located on MM 77, this place is close to many restaurant and tourist sites. Just a few... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,840
    / Month
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Refrigerator
    • Balcony
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Washer
    • DVD Player
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Great location canal front on the ocean side of Lower Matecumbe Key. The home sits on a double lot giving lots of space. The home wraps around a large boat basin for ample dockage. At times we have kept three 26 to 28 ft center console fishing boats here. This is a perfect dock setting to work... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $588
    / Night
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    1 / 19
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Private Outdoor...
    • Waterfront
    • DVD Player
    • Air Conditioning
    • Stereo System
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $206
    / Night
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    1 / 24
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Satellite TV
    • Hot Tub
    • Deck
    • Boat Available
    • Air Conditioning
    • Water Views
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Newly remodeled mobile home cottage is more than you've imagined so far. Enjoy the bright open living area with panoramic horizon view from the kitchen/living room. Open the 2 sets of French Doors to bring the outside, in. Sit on the wrap around deck to watch the Sun Rise out of the water, year... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $137
    / Night
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    1 / 22
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Enquiry
    Amenities & Details
    • Washer
    • Satellite TV
    • Air Conditioning
    • Stereo System
    • Internet Access
    • DVD Player
    • Deck
    • Dryer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL 1 MONTH: Villa Riolo is an updated single family stilt home and perfect for your next holiday in Islamorada! It comfortably sleeps 6 in two bedrooms. This home has been meticulously cared for over the years and for the first time the owners are offering you an opportunity to share... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $3,840
    / Week
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    1 / 29
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Enquiry
    Amenities & Details
    • Air Conditioning
    • Dryer
    • Washer
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful four bedroom, Ocean Front home with private beach in sunny Islamorada (near Key Largo). Welcome to our little slice of paradise in the Florida Keys! Come and relax at our beautiful ocean front home with breathtaking, panoramic views of the Atlantic ocean. This spit level home is located... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $240
    / Night
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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Make Enquiry
    Amenities & Details
    • DVD Player
    • Deck
    • Satellite TV
    • Air Conditioning
    • Dryer
    • Washer
    • Stereo System
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM RENTAL 1 MONTH: Location, location, location! This home has it all - ocean side Lower Matecumbe location, totally remodeled in 2009. Relax by the cocktail pool or sunbathe in the private roof top sunning area. There are blue water ocean views from almost every room in this home. It is... View all property information
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    Location Information
    Islamorada, Florida Keys
    From
    $490
    / Night
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    1 / 24
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Enquiry
    Amenities & Details
    • Dryer
    • Internet Access
    • Satellite TV
    • Washer
    • Air Conditioning
    • DVD Player
    • Stereo System
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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
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    Location Information
    Islamorada, Florida Keys