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House Rentals and Cottages 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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    1 / 19
    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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    4.5 of 5 stars (7) Very good
    1 Bedroom / 1 Bathroom / Sleeps 3
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    3.5 of 5 stars (2) Average
    1 Bedroom / 1 Bathroom / Sleeps 4
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    • Sauna
    • Ocean Views
    • Air Conditioning
    • Wi-Fi
    • TV
    • Watersports Nearby
    • DVD Player
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Come enjoy our home away from home. Perfect for a couples retreat. Enjoy your own fully equipped condo. Sip coffee on the balcony and watch the beautiful sunrise. Read one of our Jimmy Buffett books and dream of running away for a life on sea. Once this salt air gets in you you will never want... View all property information
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    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed June 4, 2015
    My husband and I stayed 10 days at this condo and loved it. It is clean, comfortable and fully equipped. We have already booked it for next spring. The beach is crushed coral...
    3 of 5 stars Reviewed April 11, 2015
    I spent a week at Sea Gulls with my 18 year old daughter. The unit was well equipped and clean. The pool and tennis courts were nice. The view was adequate. To the left, a...
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    1 / 25
    2 Bedrooms / 3 Bathrooms / Sleeps 6
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    • Satellite TV
    • DVD Player
    • Internet Access
    • There Are Tennis...
    • Waterfront
    • Watersports Nearby
    • Air Conditioning
    • Water Views
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    1 / 24
    3 Bedrooms / 3 Bathrooms / Sleeps 8
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    • Refrigerator
    • Washer
    • Air Conditioning
    • Internet Access
    • Patio
    • Dryer
    • DVD Player
    • Satellite TV
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    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
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    • 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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    Islamorada, Florida Keys 33036
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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
    Suitability
    • 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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    1 / 33
    4 Bedrooms / 5 Bathrooms / Sleeps 10
    traveler have booked this property
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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 / 23
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    • Watersports Nearby
    • Terrace
    • Air Conditioning
    • Linens Provided
    • Grill
    • Wi-Fi
    • Balcony
    • Parking
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    Enjoy spectacular water views from the private petite beach, large TIKI hut, boat dock and marina, You'll be just steps away from the ocean, Enjoy spectacular water views and amazing sunsets, just steps away from Founder's park with private beach, private kiddie pool,and play area plus large... 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
    traveler have booked this property
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    Amenities & Details
    • Private Outdoor...
    • Gym
    • Deck
    • Air Conditioning
    • Waterfront
    • Washer
    • Internet Access
    • TV
    Suitability
    • 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 / 21
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    traveler have booked this property
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    Amenities & Details
    • DVD Player
    • Waterfront
    • Internet Access
    • Washer
    • Water Views
    • Deck
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Relax and enjoy a peaceful getaway in beautiful Islamorada, Florida. This unique home is nestled on a bay overlooking the ocean. We are located on Lower Matecumbe Key just a few miles south of the hustle and bustle of downtown Islamorada. This is a spacious three bedroom with vaulted ceilings, a... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed November 18, 2014
    We stayed at Captains Cove again for our annual fishing weekend. Cindy, the new owner, has made several updates to the house, deck and dock which enhanced the property since our...
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    1 / 20
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • Balcony
    • Patio
    • Terrace
    • Satellite TV
    • Linens Provided
    • Refrigerator
    • Stove
    • Towels Provided
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • ?
    • 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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    Islamorada, Florida Keys 33070
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    $229
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • DVD Player
    • Housekeeping...
    • TV
    • Wi-Fi
    • Shared Outdoor Pool...
    • Watersports Nearby
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • ?
    • ?
    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... View all property information
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    Islamorada, Florida Keys 33036
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    $139
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    1 / 4
    1 Bedroom / 1 Bathroom / Sleeps 2
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    • Grill
    • Shared Outdoor Pool...
    • Stereo System
    • DVD Player
    • Wi-Fi
    • Air Conditioning
    • TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • 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... View all property information
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    Islamorada, Florida Keys 33136
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    $2,800
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    1 / 8
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Make Inquiry
    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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    Islamorada, Florida Keys 33036
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    $428
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    1 / 21
    3 Bedrooms / 3 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • 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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    $300
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    1 / 29
    5 of 5 stars (22) Excellent
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Reviews (22) Make Inquiry
    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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    5 of 5 stars (18) 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 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...
    5 of 5 stars Reviewed April 21, 2015
    The apartment is well appointed with comfortable furniture and plenty of crockery and cutlery. The building is quiet and the view from the balcony over the pool and dock out to...
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    1 / 21
    5 of 5 stars (3) Excellent
    2 Bedrooms / 3 Bathrooms / Sleeps 6
    travelers have booked this property
    Overview Reviews (3) Make Inquiry
    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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    1 / 19
    2 Bedrooms / 2 Bathrooms / Sleeps 5
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    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Housekeeping...
    • 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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    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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    $275
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    1 / 29
    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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    Location Information
    Islamorada, Florida Keys 33036
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    $2,775
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    1 / 14
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • 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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    Location Information
    Islamorada, Florida Keys 33036
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    $5,000
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    1 / 10
    2 Bedrooms / 2 Bathrooms / Sleeps 4
    traveler have booked this property
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    Amenities & Details
    • Water Views
    • Internet Access
    • Waterfront
    • Hot Tub
    • Stereo System
    • Satellite TV
    • Air Conditioning
    • Sauna
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Imagine waking to the beauty of a sunrise brimming over the aqua seas. Linger in your master suite and watch the ocean shift through a prism of aqua, blues and emerald greens. Gentle breezes waft through this two bedroom, two bath condo with comfortable appointments and an elegant sea glass... View all property information
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    Islamorada, Florida Keys 33036
    From
    $2,490
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    1 / 17
    3 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Washer
    • Internet Access
    • Dryer
    • Stereo System
    • Air Conditioning
    • DVD Player
    • Deck
    • Satellite TV
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    The house is perfect for those traveling with different age groups, in-laws, teenagers or 2 families. The house is extra clean and has modern furnishings. It has 3 bedrooms, 2 baths. Upstairs there are 2 bedrooms, 1 bath with a new leather couch that pulls out to a queen size bed. Downstairs an... View all property information
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    Islamorada, Florida Keys 33036
    From
    $495
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    1 / 12
    3 Bedrooms / 3 Bathrooms / Sleeps 7
    Overview Make Inquiry
    Amenities & Details
    • 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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    Location Information
    Islamorada, Florida Keys 33036
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    $250
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    2 Bedrooms / 3 Bathrooms / Sleeps 6
    traveler have booked this property
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    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    This Coastal Conch Style Cottage has been recently updated to accommodate vacation renters and their families. The cottage has all new furnishings and accessories that offers a 'home away from home' feel. The Coastal style conch cottage is located in the gated community, ocean front resort... View all property information
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    Location Information
    Islamorada, Florida Keys 33040
    From
    $4,900
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    1 / 9
    2 Bedrooms / 2 Bathrooms / Sleeps 4
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    Amenities & Details
    • 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: November: 4950 January through May: $5000 single month, three or more months $4900.each month PLEASE DO NOT SUBMIT A REQUEST FOR A PERIOD LESS THAN ONE FULL MONTH KINDLY NOTE: MONTHLY RENTAL. To maintain the beauty of Beacon Reef, rental contracts must be for no less than a... View all property information
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    Islamorada, Florida Keys 33036
    From
    $300
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    1 / 22
    4.5 of 5 stars (3) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (3) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Waterfront
    • Wi-Fi
    • Watersports Nearby
    • Horse Riding Nearby
    • Water Views
    • TV
    • There Are Tennis...
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    **We do not use the optional calendar feature on this listing. ** ***For holiday weeks, lobster opening week, and lobster mini season week rates will be higher.*** This is a very popular rental, so book your preferred week well in advance of peak season! I reply to EVERY inquiry. If you do not... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 22, 2015
    My husband and I just returned from Casa Rio. The home was clean and comfortable and quaint. The outdoor area was beautiful, charming and relaxing. We had access to bicycles...
    5 of 5 stars Reviewed April 14, 2015
    We had a wonderful time at this waterfront paradise. Waking up in the morning to a beautiful view of the waterway outside the window of our bedroom. Not to mention enjoying the...
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    $2,000
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    1 / 25
    2 Bedrooms / 2 Bathrooms / Sleeps 5
    Overview Make Inquiry
    Amenities & Details
    • Shared Outdoor Pool...
    • Hot Tub
    • Gym
    • Balcony
    • Internet Access
    • Patio
    • Satellite TV
    • Refrigerator
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    MINIMUM STAY: 29 DAYS Exceptional condo with panoramic views of the Atlantic Ocean. This condo is in one of the most popular condo complexes in Islamorada - The Palms of Islamorada. Comfortably furnished and ready for your arrival this unit offers an updated kitchen with Corian counters,... View all property information
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    Islamorada, Florida Keys 33036
    From
    $85
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    1 / 19
    1 Bedroom / 1 Bathroom / Sleeps 2
    Overview Make Inquiry
    Amenities & Details
    • Refrigerator
    • Grill
    • Balcony
    • Air Conditioning
    • DVD Player
    • Private Fishing...
    • TV
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    The Hippie Home was Built with Love in the Sunshine of the Spirit. Nestled in Islamorada, the Sportfishing Capital of the World. The Neighborhood is Quiet and Pet Friendly with a Private Beach and Tiki Hut. Close to Restaurants, Shopping, Recreation, Fishing Charters, Scuba Diving, and Snorkeling.... View all property information
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    Islamorada, Florida Keys 33036
    From
    $100
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    1 / 23
    1 Bedroom / 1 Bathroom / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • DVD Player
    • Waterfront
    • There Are Tennis...
    • Satellite TV
    • Ocean Views
    • Watersports Nearby
    • Air Conditioning
    • Water Views
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • ?
    • x
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Come watch the sunrise over the ocean while sipping coffee on the patio. If you love to fish, play in the water, or just relax this is the destination for you. Situated on the old highway ocean side in a small quiet RV Park. The park has a small sand beach with swimming. The roads in the park are... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    From
    $200
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    1 / 11
    2 Bedrooms / 2 Bathrooms / Sleeps 10
    Overview Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Linens Provided
    • Wi-Fi
    • Secure Parking
    • Towels Provided
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    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
    From
    $975
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    1 / 20
    4 of 5 stars (1) Very good
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Fireplace
    • Deck
    • Boat Available
    • Water Views
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    About this property
    Two Acre Ocean Front Estate in the heart of Islamorada. Over 200 feet of ocean front with an ocean front pool with two sides in the Atlantic. A large flat beach area with a large patio at the ocean's edge. The estate has two villas, both have a full kitchen, living room, pull out sofas and... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 stars Reviewed June 16, 2015
    A spacious place for a family wanting to relax but have fun. Islamorada is very peaceful but has lots to do. We loved this place because there was plenty of room for the kids...
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    $4,000
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    Studio / 3 Bathrooms / Sleeps 4
    Overview Make Inquiry
    Amenities & Details
    • Wi-Fi
    • Refrigerator
    • Washer
    • Waterfront
    • Dryer
    • Air Conditioning
    • TV
    • Grill
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    This delightful 2 bedroom 2 bathroom with a detached 1 bedroom 1 bath downstairs is located on a quiet canal in Plantation Key at mile maker 90 ocean side. This home has a renovated kitchen and is beautifully decorated throughout. The property is fenced in and has amazing water views. You won't... View all property information
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    Islamorada, Florida Keys 33036
    From
    $120
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    1 / 29
    3 Bedrooms / 2 Bathrooms / Sleeps 8
    Overview Make Inquiry
    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
    From
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    1 / 18
    4 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Make Inquiry
    Amenities & Details
    • Waterfront
    • Satellite TV
    • Wi-Fi
    • Water Views
    • Hot Tub
    • Stereo System
    • DVD Player
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • Elder access
    • x
    • x
    About this property
    This home is located minutes from Snake Creek Channel and is minutes from ocean and bay access. 1.5 mile north of the world famous Holiday Isle Tiki Bar and less than 2 hours away from Key West. If you enjoy fishing, snorkeling, diving this is the perfect for you . Located at Plantation Key Colony.... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    From
    $170
    / Night
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    1 / 26
    5 of 5 stars (1) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 4
    Overview Reviews (1) Make Inquiry
    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Satellite TV
    • Water Views
    • Dryer
    • Grill
    • Washer
    • Waterfront
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Welcome to Sol Y Mar SOL Y MAR is 2,500Sq.Ft. of Living Space,Three (3) Bedrooms, Two (2) Bathrooms on Three (3) Levels. Property is located in Tavernier, in Islamorada, Florida (MM90). The Center of the Keys, 1.5 Hours to Miami, 1.5 Hours to Key West; Shopping, Restaurants, Theaters, Sunset... View all property information
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    Islamorada, Florida Keys 33070
    5 of 5 stars Reviewed April 25, 2015
    Our family of 5 adults spent a week at Sol Y Mar in Tavernier Florida. We were fortunate to have Nestor Loredo as our agent. The house was all as promised. Nestor met us the and...
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    $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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    $1,040
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    1 / 19
    5 of 5 stars (3) Excellent
    1 Bedroom / 1 Bathroom / Sleeps 3
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    Amenities & Details
    • Ceiling Fans
    • Satellite TV
    • Grill
    • Internet Access
    • Refrigerator
    • Parking
    • Patio
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights You can have it all – privacy and convenience. The owners of this wonderful property called Sunshine Place are willing to share a portion of their piece of Paradise with you. The ground level living area of this home is perfect for one or two people who treasure... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed March 13, 2015
    If your looking for the whole package in one this is the place. View, comfortable, privacy and location. Best place I've stayed in the keys, hands down!
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    $500
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    1 / 38
    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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    $150
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    1 / 28
    5 of 5 stars (26) Excellent
    Studio / 1 Bathroom / Sleeps 2
    Overview Reviews (26) Make Inquiry
    Amenities & Details
    • Boat Available
    • Private Fishing...
    • Internet Access
    • Water Views
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • DVD Player
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • x
    • Smoking allowed
    • 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. Save almost 50% and book July 11 - 18 for only $900 plus tax! This is a... View all property information
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    Location Information
    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed April 16, 2015
    Ewa and Peter were incredible hosts at this beautiful property. We felt right at home immediately and had so many activities to do plus Ewa and Peter had loads of great tips...
    4 of 5 stars Reviewed January 19, 2015
    Great place for a couples private getaway. Host's are very pleasant & leave you to yourselves, but are there if you need anything. No stove, you have to use a microwave/convection...
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    $800
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    1 / 45
    5 of 5 stars (2) Excellent
    4 Bedrooms / 3 Bathrooms / Sleeps 8
    Overview Reviews (2) Make Inquiry
    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
    $1,500
    / Night
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    1 / 15
    5 of 5 stars (1) Excellent
    3 Bedrooms / 3 Bathrooms / Sleeps 10
    Overview Reviews (1) Make Inquiry
    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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    Location Information
    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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    $1,250
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    1 / 27
    4.5 of 5 stars (4) Very good
    2 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (4) Make Inquiry
    Amenities & Details
    • Satellite TV
    • Water Views
    • Shared Outdoor Pool...
    • Grill
    • Refrigerator
    • Balcony
    • Patio
    • Internet Access
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    • ?
    About this property
    Minimum Rental: 7 Nights (Saturday to Saturday) BROCKHAUS ON THE GULF is an end unit townhouse on the water's edge with water views on 3 sides! The main living area faces the Florida Bay, one side faces the inlet leading to the marina basin and the back faces the marina. The panoramic open... View all property information
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    Location Information
    Islamorada, Florida Keys 33070
    4 of 5 stars Reviewed June 1, 2014
    Having stayed in other properties at Futura Yacht Club over the years, I can honestly say that this was by far the nicest. The kitchen had been recently renovated with new white...
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    $800
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    1 / 30
    4.5 of 5 stars (9) Very good
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (9) 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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    Islamorada, Florida Keys 33070
    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...
    5 of 5 stars Reviewed January 13, 2012
    The condo was great! It was clean and located in a great place in the Keys. There were many excellent restaurants in the area when you wanted to go out, and a full kitchen when...
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    $2,900
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    1 / 29
    5 of 5 stars (2) Excellent
    3 Bedrooms / 2 Bathrooms / Sleeps 6
    Overview Reviews (2) Make Inquiry
    Amenities & Details
    • Deck
    • Wi-Fi
    • Water Views
    • Boat Available
    • Satellite TV
    • DVD Player
    • Air Conditioning
    • Stereo System
    Suitability
    • Pet-friendly
    • Wheelchair access
    • Child-friendly
    • x
    • x
    • ?
    • Smoking allowed
    • Elder access
    • x
    About this property
    Location: Islamorada, Islamorada Area, Florida Keys, Florida, USA View Map Accommodations: House, 3 Bedrooms, 2 Baths, sleeps 6 122 Nautilus Drive, Islamorada, Florida Keys mile marker 74.5 bay side, White Marlin Beach located 75 miles south of Miami and 75 miles North of Key West. It has three... View all property information
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    Islamorada, Florida Keys 33036
    5 of 5 stars Reviewed May 29, 2015
    We thoroughly enjoyed our week here, with our adult children. The home is very clean and well-maintained and beautifully decorated and furnished in a tropical style. The outdoor...
    5 of 5 stars Reviewed May 12, 2014
    We loved staying at Villa Marlin, and the owner was very helpful before and during our stay. The home is prettier than the pictures, and we felt right at home!
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    $18,000
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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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    $1,100
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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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    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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    $179
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    1 / 5
    1 Bedroom / 1 Bathroom / Sleeps 3
    traveler have booked this property
    Overview Make Inquiry
    Amenities & Details
    • TV
    • Deck
    • Watersports Nearby
    • Air Conditioning
    • Stereo System
    • Patio
    • Wi-Fi
    • DVD Player
    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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    Location Information
    Islamorada, Florida Keys 33036