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Rentals with Pool in Islamorada, FL

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    Travelers to Islamorada are booking December dates now. Secure your vacation rental today, and have the perfect trip.
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    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
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    5 of 5 stars (4) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    3.5 of 5 stars (2) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
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    1 Bedroom / 1 Bathroom / Sleeps 3
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    About this property
    The Moroccan room is a fabulous honeymoon destination with king size canopy bed. Room features a/c, coffee maker, heat, microwave, refrigerator, TV, WiFi. Enormous bathroom with sunken tub and terrycloth robes to lounge in includes full breakfast. LOCATED IN A QUIET, SECLUDED, TROPICAL SETTING YET... View all property information
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    Islamorada, Florida Keys 33036
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    4 Bedrooms / 5 Bathrooms / Sleeps 10
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    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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    2 Bedrooms / 2 Bathrooms / Sleeps 10
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    • Towels Provided
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    About this property
    Make yourself at home in your own private paradise in the Fabulous Florida Keys! The exclusive Executive Bay Club is a gated community with 24 hour security situated waterfront on the Florida Bay in Islamorada, just an hour from the hussle and bustle of Miami, yet a world away. Enjoy five-star... View all property information
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    Islamorada, Florida Keys 33036
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    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Stereo System
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    • Refrigerator
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    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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    Islamorada, Florida Keys 33136
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    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Private Fishing...
    • Children's Pool
    • Water Views
    • Waterfront
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • DVD Player
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    2 bedrooms, 2 full bathrooms, 1 half bathroom, sleeps 6 This magnificent oceanfront home is at Mile Marker 85 in exclusive Angler's Reef - 52 homes . Quaint streets & walking paths wind through this village-styled retreat. Enjoy a drink in the lushly landscaped pool area overlooking the ocean or on... View all property information
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    Islamorada, Florida Keys 33023
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
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    • Water Views
    • Waterfront
    • Boat Available
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This property is a single family home, 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 by onsite securty. Rates start at $2,475 per week plus 12.5%... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 25
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    travelers have booked this property
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    • Private Outdoor...
    • Gym
    • Deck
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    • TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed November 16, 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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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    Amenities & Details
    • DVD Player
    • Stereo System
    • Internet Access
    • Satellite TV
    • Watersports Nearby
    • Waterfront
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed August 20, 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 June 30, 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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    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
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    • Satellite TV
    • DVD Player
    • Internet Access
    • There Are Tennis...
    • Waterfront
    • Watersports Nearby
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This beautiful villa has all new furnishings and is located in the exclusive oceanfront gated community of Angler's Reef in Islamorada at Mile Marker 84. Angler's reef is a luxury retreat resort framed by mangroves and the clear waters of the Atlantic ocean with 52 colonial detached villas set... View all property information
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    Islamorada, Florida Keys 33036
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    $495
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    3 Bedrooms / 3 Bathrooms / Sleeps 7
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    • TV
    • Swingset
    • DVD Player
    • Private Outdoor...
    • Wi-Fi
    • Housekeeping...
    • Watersports Nearby
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Beautiful 3 bedroom / 2 bath in the heart of Islamorada. With a pool. A short walk to Chica Lodge and Moorings Village and all the best restaurants in the Keys like Morada Bay. Located in the best location of the Florida Keys. The house has many different places to relax, lounge and forget all the... View all property information
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    Islamorada, Florida Keys 33036
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    $428
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Water Views
    • Private Fishing...
    • Air Conditioning
    • DVD Player
    • Waterfront
    • Satellite TV
    • Internet Access
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Lower Matecumbe Key condo description Welcome to paradise! This beautiful three bedroom, two and a half bath end unit condominium sleeps 6 people. Master bedroom has a king bed with direct access to the water front balcony. Second bedroom has a queen bed and the third has two twin beds. Brand new... View all property information
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    Islamorada, Florida Keys 33036
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    1 / 41
    5 of 5 stars (3) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Shared Tennis Court
    • Wi-Fi
    • Satellite TV
    • Private Fishing...
    • Air Conditioning
    • Waterfront
    • Watersports Nearby
    • Water Park Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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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    $258
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    1 / 21
    5 of 5 stars (3) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
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    Amenities & Details
    • Internet Access
    • Waterfront
    • Hot Tub
    • DVD Player
    • Air Conditioning
    • Satellite TV
    • Water Views
    • Private Tennis Court
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed February 7, 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 September 2, 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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    2 Bedrooms / 4 Bathrooms / Sleeps 4
    traveler have booked this property
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    • Linens Provided
    • Ocean Views
    • Grill
    • Air Conditioning
    • Balcony
    • Parking
    • Wi-Fi
    • Elevator/Lift access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    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
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    Islamorada, Florida Keys 33070
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    5 of 5 stars (19) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 4
    travelers have booked this property
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    Amenities & Details
    • Satellite TV
    • Air Conditioning
    • Waterfront
    • Stereo System
    • Sauna
    • Internet Access
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed July 19, 2015
    This was our second at Summer Sea and Rosella and I will be back again. We met with Richard to gain entry as before, who took the time to show us all the improvements made to...
    5 of 5 stars Reviewed April 30, 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...
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    $2,775
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    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Boat Available
    • TV
    • DVD Player
    • Watersports Nearby
    • There Are Tennis...
    • Air Conditioning
    • Stereo System
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • 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 by onsite security. Rates... View all property information
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    Islamorada, Florida Keys 33036
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    $1,596
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 6
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    • Air Conditioning
    • Water Park Nearby
    • Ocean Views
    • Private Fishing...
    • Water Views
    • TV
    • Wi-Fi
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Fabulous vacation home in the exclusive gated oceanfront community of Anglers Reef at mile marker 85 in Islamorada of the Florida Keys. Luxurious beach decor, plush furnishings, spacious accommodations that comfortably sleep 6 adults and children of all ages will feel right at home with the many... View all property information
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    Islamorada, Florida Keys 33036
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    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Satellite TV
    • Waterfront
    • Private Fishing...
    • DVD Player
    • Hot Tub
    • Air Conditioning
    • Children's Pool
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    AVAILABLE: Present through November 26, 2015. April 2016 and beyond. KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a month. This helps keep the property exclusive, serene and beautifully respected--something you will truly enjoy... View all property information
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    Islamorada, Florida Keys 33036
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    5 Bedrooms / 5 Bathrooms / Sleeps 10
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    • Air Conditioning
    • TV
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Hot Tub
    • Ocean Views
    • Watersports Nearby
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    About this property
    Islamorada Venetian Shores luxury waterfront 5BD/5BA with 100' dock and boat lift, custom pool with spa and waterfall, elevator & private master suite on the 3rd floor. Instant big boat access to both the ocean and bay from 100' wide, deep canal. Spacious home offers over 5,000 sf including porches... View all property information
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    Islamorada, Florida Keys 33036
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    $3,290
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    1 / 24
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Waterfront
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Watersports Nearby
    • Wi-Fi
    • Swingset
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Canal-front house, quiet and in the nicest of neighborhoods (Plantation Key Colony). Situated on the bayside on Mile Marker 90. All remodeled,white tiled floor, furnished in wicker/rattan and decorated with the ocean & beach ambiance in mind. Boat dockage in the back and easy access to few boat... View all property information
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    Islamorada, Florida Keys 33070
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    $120
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    1 / 29
    3 Bedrooms / 2 Bathrooms / Sleeps 8
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    Amenities & Details
    • Shared Tennis Court
    • Satellite TV
    • Private Tennis Court
    • DVD Player
    • Private Outdoor...
    • Air Conditioning
    • Internet Access
    • Private Fishing...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ENJOYABLE, CENTRAL LOCATION, PLANTATION KEY, 3 bedroom + loft, 2 bath; 1400 sf 2 story, all bedrooms and 1 full bath are upstairs & downstairs is the living area and 1 additional full bath. The unit is clean, comfortable, quiet and restful. The community is gated with security, no pets are allowed;... View all property information
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    Islamorada, Florida Keys 33036
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    $179
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    1 Bedroom / 1 Bathroom / Sleeps 3
    traveler 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
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    $3,255
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    1 / 49
    5 of 5 stars (6) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (6) Make Inquiry
    Amenities & Details
    • Satellite TV
    • DVD Player
    • Watersports Nearby
    • Air Conditioning
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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 May 13, 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 February 13, 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 (23) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (23) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • DVD Player
    • Internet Access
    • Waterfront
    • Satellite TV
    • Stereo System
    • Water Views
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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 March 24, 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 May 19, 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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    $800
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
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    Amenities & Details
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $107
    / Night
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    1 / 15
    5 of 5 stars (12) Excellent
    2 Bedrooms / 1 Bathroom / Sleeps 6
    Overview Reviews (12) Make Inquiry
    Amenities & Details
    • DVD Player
    • Waterfront
    • Satellite TV
    • Children's Pool
    • Internet Access
    • Air Conditioning
    • Playground
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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 July 7, 2015
    Me, my husband, two teenagers and my mother-in-law stayed. Everything was nice and clean and the place is easy to find. I snorkeled right off from the little private beach every...
    5 of 5 stars Reviewed July 9, 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...
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    $129
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    1 / 9
    5 of 5 stars (1) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
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    Amenities & Details
    • Housekeeping...
    • Stereo System
    • Watersports Nearby
    • Air Conditioning
    • Wi-Fi
    • Shared Outdoor Pool...
    • DVD Player
    • TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • Smoking allowed
    • 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 YET... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed July 26, 2015
    This cute place was a perfect stop on a little crawl down the keys I planned for me and my mom. I loved the garden and rooftop patio. Very good service and hosts. Thank you Mrs...
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    $185
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    1 / 6
    4 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Internet Access
    • Stereo System
    • Waterfront
    • Water Views
    • DVD Player
    • Boat Available
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    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
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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed November 18, 2014
    Just wanted to thank Bill for a wonderful four days at his place. Condo has tremendous views -- you are on the top floor -- amenities are great as well as the sleeping...
    4 of 5 stars Reviewed July 7, 2014
    The pool is sparkling clean. You can enjoy the ocean-view from the pool area. The balcony is a wonderful place to hang out and relax. Close to everything.
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    $4,480
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    1 / 11
    5 of 5 stars (4) Excellent
    5 Bedrooms / 4 Bathrooms / Sleeps 9
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Private Outdoor...
    • Water Views
    • Waterfront
    • DVD Player
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    From
    $1,100
    / Week
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    1 / 16
    5 of 5 stars (1) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • DVD Player
    • Washer
    • Water Views
    • Air Conditioning
    • Stereo System
    • Satellite TV
    • Waterfront
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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 January 6, 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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    $800
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    1 / 30
    4.5 of 5 stars (10) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (10) Make Inquiry
    Amenities & Details
    • Shared Tennis Court
    • Water Views
    • Satellite TV
    • Waterfront
    • Air Conditioning
    • DVD Player
    • Internet Access
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed July 23, 2015
    Our group consisted of 5 adults and 1 teenager and we had a great time. We had all of the room we needed for sleeping, food prep and eating. Everything else was outside in the...
    3 of 5 stars Reviewed March 4, 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...
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    From
    $3,300
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    1 / 19
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Microwave
    • Water Views
    • Air Conditioning
    • Dishwasher
    • Porch
    • TV
    • Shared Outdoor Pool...
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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
    $1,500
    / Night
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • Ocean Views
    • Waterfront
    • TV
    • Stereo System
    • DVD Player
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    About this property
    The Royal Palm, South - Ocean Front Home Catch Bonefish and Tarpon from Our 450-Foot Fishing Pier. Inspired by owner Phil Sena —with nothing compromised— this luxurious Caribbean home is on the ocean's edge with 180 degrees of unobstructed ocean views and sunrises. Complete privacy. Full... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 24, 2015
    Rolled out of bed early every day this week with my boys and family friends for my favorite commute: 50 yard walk to a private boat slip at the resort. We rented a boat...
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    $89
    / Night
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    1 / 7
    1 Bedroom / 1 Bathroom / Sleeps 2
    travelers have booked this property
    Overview Make Inquiry
    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
    $7,500
    / Month
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    1 / 9
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Private Outdoor...
    • DVD Player
    • Waterfront
    • Water Views
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed July 23, 2015
    We stayed here with four friends. This house was beautifully decorated and the grounds were well kept. It was very clean and lots of room. We really love the totally private third...
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    $4,500
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    1 / 13
    4 of 5 stars (1) Very good
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Internet Access
    • Water Views
    • Deck
    • Waterfront
    • Satellite TV
    • Washer
    • Private Outdoor...
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • 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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    Location Information
    Islamorada, Florida Keys 33036
    From
    $3,000
    / Week
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    1 / 27
    Studio / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Washer
    • TV
    • Wi-Fi
    • Dryer
    • Patio
    • Waterfront
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    With the weather getting hotter, the water is once again the place to be in South Florida. Fortunately, you'll barely have to venture out your back door to take a soak while vacationing at this quaint oceanfront conch house. Located on Islamorada's Lower Matecumbe Key, near mile marker 76, this... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $18,000
    / Month
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    1 / 11
    5 of 5 stars (1) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Waterfront
    • Water Views
    • Internet Access
    • Satellite TV
    • Boat Available
    • Deck
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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 June 16, 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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    From
    $8,950
    / Week
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    1 / 13
    5 Bedrooms / 7 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Water Views
    • Hot Tub
    • Private Outdoor...
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Waterfront
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • 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
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $5,500
    / Week
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    1 / 14
    4 Bedrooms / 4 Bathrooms / Sleeps 8
    Overview Make Inquiry
    Amenities & Details
    • Hot Tub
    • Air Conditioning
    • Waterfront
    • Private Outdoor...
    • Water Views
    • Internet Access
    • Satellite TV
    • Washer
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    VR-202 You can not rent this property for less than one week. The Gardens is a 4/4 private home surrounded by impeccably landscaped grounds. This property has over 50 types of palms, abundant orchids, and bougainvilleas. At your doorstep is a breathtaking view of the Atlantic Ocean where you can... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $6,000
    / Week
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    1 / 22
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Private Outdoor...
    • Satellite TV
    • Waterfront
    • Deck
    • Water Views
    • DVD Player
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Village Permit # VR-204You can not rent this property for less than one week.Sit back, relax, a light breeze, gaze the blue waters of the Atlantic Ocean….and be lost. Southern Comfort is the perfect vacation home in the Florida Keys, located at MM 77. This very private Estate sits on 3+ acres... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $12,000
    / Week
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    1 / 49
    5 of 5 stars (13) Excellent
    10 Bedrooms / 8 Bathrooms / Sleeps 20
    Overview Reviews (13) Make Inquiry
    Amenities & Details
    • Water Views
    • Stereo System
    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Outdoor...
    • Waterfront
    • Ping Pong Table
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Got a large group that wants to 'get away from it all'? Or do you need lots of space for a family reunion or wedding? This is the perfect solution! Terrific location, beautiful view, two private pools for you to enjoy... And since it's 4 separate homes, you aren't right on top of each other. Wide... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 7, 2015
    Great location. Very clean and relaxing. If you are looking for a waterfront view, this place does not have it but it is only a very short walk down to the dock to have a...
    5 of 5 stars Reviewed October 17, 2014
    We stayed at the Alligator Reef Luxury estates as a group of 18 people. This was a business gathering to bring our team together from all over the world, and this estate couldn’t...
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    From
    $3,500
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    1 / 17
    4 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Air Conditioning
    • Private Outdoor...
    • Hot Tub
    • Satellite TV
    • Water Views
    • Internet Access
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    About this property
    Village Permit #VR-138 You can not rent this property for less than one week. An affordable ocean front, beach, pool and hot tub home.   This popular home is located in south Islamorada.  Three bedrooms, two baths, living kitchen and dining area are upstairs. Downstairs is a separate area with a... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $19,900
    / Month
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    1 / 15
    5 Bedrooms / 5 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Internet Access
    • Water Views
    • Deck
    • Satellite TV
    • Shared Outdoor Pool...
    • Air Conditioning
    • Hot Tub
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    ****This house cannot rent for less than 28 days, per County Ordinance**** Breathtaking Sunset's, Breathtaking Home. Pineapple Plantation is an unbelievable gated, New Bay Front home. It is perfectly located a Mile Marker 89, Islamorada. Boasting 5 Bedroom Suite's, Gourmet kitchen with an ocean... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $2,450
    / Week
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    1 / 19
    5 of 5 stars (3) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Inquiry
    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 March 25, 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 January 19, 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
    $805
    / Week
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    1 / 29
    4.5 of 5 stars (3) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Washer
    • Dryer
    • Wi-Fi
    • Stereo System
    • Shared Outdoor Pool...
    • Satellite TV
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Beautiful three 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... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed May 1, 2015
    Our townhouse was clean, spacious, & quiet. Lovely updated kitchen and laundry. The pool was delightful, and the beach & dock were very enjoyable as well. Very peaceful...
    5 of 5 stars Reviewed March 28, 2015
    I really enjoyed my stay! The place was great. I loved the layout. Very roomy. Enough space for everyone. The pool was great and even played a little tennis.
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    From
    $1,325
    / Week
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    1 / 23
    5 of 5 stars (1) Excellent
    2 Bedrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Water Views
    • TV
    • Dryer
    • Waterfront
    • Washer
    • Grill
    • Wi-Fi
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    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