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Beach House Rentals in Florida Keys, FL

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    1 / 17
    4.5 of 5 bubbles (32) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    1 / 14
    4.5 of 5 bubbles (38) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 8 | Quick View
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    1 / 17
    5 of 5 bubbles (16) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    1 / 20
    5 of 5 bubbles (24) Excellent
    Key Largo
    2 Bedrooms, 4 Bathrooms, Sleeps 4 | Quick View
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    • DVD Player
    • Air Conditioning
    • Patio
    • Ocean Views
    • Wi-Fi
    • Washer
    • Satellite TV
    • Waterfront
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Charming and secluded CBS construction seaside cottage with all of the comforts. Two bedrooms each with queen size bed and private bath. Also a third bathroom in the main area for your convenience. Fully equipped kitchen/dining room with a bar cabinet and a washer/dryer closet. For your outdoor... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 1 week ago
    We really enjoyed our stay, the owner is extremely helpful. The property is amazing don't hesitate to book !
    5 of 5 bubbles Reviewed February 24, 2017
    The waterfront Key Largo Bayside Cottage was in fact, Paradise. There was plenty of space for both couples. The outside accommodations were superb. We spent lots of time on the...
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    1 / 55
    5 of 5 bubbles (19) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Grill
    • Waterfront
    • Satellite TV
    • Hot Tub
    • Wi-Fi
    • Air Conditioning
    • Ocean Views
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Its all about being newly renovated, on the top floor of the best building with the largest end unit with the most windows - twelve. You will have the most magnificent unobstructed ocean views from the living room, kitchen, master & guest bedrooms and balcony. This unit sleeps four adults, (the... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed 1 week ago
    Beautiful waterfront condo with stunning views of water and wildlife. This condo was exceptional in that it has all the amenities of home in the most pristine setting. The...
    5 of 5 bubbles Reviewed 4 weeks ago
    We've stayed at various units in the Ocean Point Complex and this building (400) and unit (4416) are by far the best! End unit on the top floor offers extra windows, all with...
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    1 / 39
    5 of 5 bubbles (36) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Internet Access
    • Waterfront
    • Air Conditioning
    • Sauna
    • Washer
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This Luxury unit is 1375 sq ft of breath taking beachfront living space in this tropical complex. Great views from the 40 foot deck which encompasses the whole unit. Every room has a spectacular view of the tropical Nature Preserve and the Atlantic Ocean. The complex is oceanfront with an Olympic... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 21, 2016
    We were so thrilled to stay in this vacation rental, My mom is in a wheelchair full time and there was enough room for her to get around, the bathroom was perfect for her. My 2...
    5 of 5 bubbles Reviewed August 5, 2016
    Best aspect: owner Kathy W. communicated as stay got closer. She even asked how we were doing the day of travel and invited us to call her with any concerns or questions. We...
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    1 / 13
    5 of 5 bubbles (7) Excellent
    Key West
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Terrace
    • Wi-Fi
    • Air Conditioning
    • Porch
    • Balcony
    • Satellite TV
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    About this property
    Located in the heart of Duval St, this unique property offers a central location to the Key West landmarks and sights. Enjoy all Key West has to offer from a historic building with a private balcony overlooking Duval St. This property features a 1 bedroom with a king size bed, full bath and... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 10, 2017
    This is a lovely place to stay,well furnished, and ideally located right in the heart of the 'action'. However, it is quite expensive, with $25 per day parking charge plus...
    5 of 5 bubbles Reviewed February 26, 2017
    5 stars. Great place, everything included, didn't have to bring anything. Old Florida style, best location, in the middle of all the action, balcony lets you view all. Restaurants...
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    1 / 23
    5 of 5 bubbles (11) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    • Air Conditioning
    • Satellite TV
    • DVD Player
    • Grill
    • Waterfront
    • Wi-Fi
    • Patio
    • Washer
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    A quite, private, waterfront residence in the lower Florida Keys, the American Caribbean. Decorated in Nautical and Tropical décor. Undeveloped property on one side and across the canal. On a boating canal with dockage for your boat, Free launching at the nearby marina and space for your boat... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed 2 weeks ago
    Went down for Thanksgiving with my wife and kids and we had a great time. The house is perfect and is located between Key West and Marathon so you are close enough to all the...
    4 of 5 bubbles Reviewed September 11, 2016
    Charming tropical cottage feel, with a deck that looked out on canal. Key deer joined us daily and that was pretty cool. Great house for us, 2 couples and our boat! Fished...
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    1 / 14
    5 of 5 bubbles (26) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Grill
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Outdoor Dining Area
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    Relax of the Island Style front porch and enjoy Key West at it's finest. Centrally located, less than a block from Duval - this Completely updated 2 Bedroom, 1 Bath will simply amaze you! High Ceilings, tall windows, full kitchen with separate dining room and plenty of space to make your Key West... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed February 14, 2017
    Rented this place for my sister's bachelorette party and we had an amazing stay. It really is walking distance to everything and the shared pool was great. It was such a bonus...
    4 of 5 bubbles Reviewed February 14, 2017
    Key West Bahama House is located in the perfect spot. Rooms are very nice and clean. The only downside in April of 2016, there was construction at the building behind and beside...
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    1 / 17
    5 of 5 bubbles (16) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Waterfront
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Washer
    • Hot Tub
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ocean Pointe Suites is located directly on the Atlantic Ocean. This unit is completely renovated and is located in building 4 which is the most desirable building. Featuring magnificent ocean views from the living room, master bedroom and porch. This unit offers 1 King bed in master bedroom, 1... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed August 30, 2016
    The property manager was very helpful. The property was recently remodeled and very clean. It was spacious enough for two couples. Two bathrooms were ideal since there were two...
    5 of 5 bubbles Reviewed August 16, 2015
    The apt. Was beautiful in an awesome location. Close to shopping areas. Marina was great. Fishing was awesome. There were lots of people diving. Lots to do too little time...
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    1 / 16
    4.5 of 5 bubbles (3) Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Balcony
    • Washer
    • Central Heating
    • Hot Tub
    • Terrace
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Ocean Pointe Suite is located directly on the Atlantic Ocean. This unit is renovated and is located in building 1. Featuring beautiful views from the living room, kitchen and porch. This unit offers 1 King bed in master bedroom, 1 Queen bed in guest bedroom, a pull out queen sofa, 400 thread count... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed September 27, 2016
    I chose this location for several reasons. We came here to attend a wedding in Key Largo, but I'm rather picky about the places I choose to stay. This place offers everything I...
    4 of 5 bubbles Reviewed July 3, 2016
    Ocean Pointe was exactly what we needed for our 5 day getaway with friends. The staff was very friendly and the condo was clean and has a kitchen equipped for cooking. The beds...
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    1 / 14
    4 of 5 bubbles (2) Very good
    Marathon
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Wi-Fi
    • Air Conditioning
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    This beautifully furnished and newly renovated condo is airy and offers all the comforts of your own home. Walk in to a spacious living room with an adjacent dining area and then onto a full kitchen with everything necessary to prepare and serve your meals. The kitchen has granite counter tops, a... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed November 30, 2016
    Great location and beautifully decorated. We had all that we needed. We did have some trouble getting in to the unit since we arrived late in the evening, but it was resolved...
    4 of 5 bubbles Reviewed November 9, 2016
    Place was great one of the best I have in in the keys but when we left they tried to say we had left the house in a mess but every room was scrubbed clean and took photos in case...
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    1 / 21
    5 of 5 bubbles (6) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • DVD Player
    • Hot Tub
    • Washer
    • Waterfront
    • Ocean Views
    • Satellite TV
    • Wi-Fi
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    We are offering for rent our beautiful, 2/2 condominium located directly on the ocean in Key Largo (Tavernier), Florida. As this is 4th floor "END" unit there are many windows that provide an open, bright feel and offer views of the ocean throughout. Our location provides direct ocean access in... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed 1 week ago
    Clean, bright, spacious, comfortable - we loved this condo. We've stayed in various condos for the past 15 years when visiting the keys. This unit was in the top 5.
    5 of 5 bubbles Reviewed February 16, 2017
    We have been renting this condo for 12 years. We are extremely happy with this condo. The condo has everything you need whether it be for a week or a month. The condo is very...
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    1 / 12
    5 of 5 bubbles (3) Excellent
    Big Pine Key
    1 Bedroom, 1 Bathroom, Sleeps 2 | Quick View
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    • DVD Player
    • Air Conditioning
    • Parking
    • Wi-Fi
    • Private Yard
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Welcome to your Big Pine Getaway! Enjoy everything Key West has to offer and the quiet evenings of Big Pine. Only a short 25 minute drive to Key West, and less than 10 minutes to the beautiful beaches of Bahia Honda State Park. You are also a quick 15 minute drive north to Marathon.. Enjoy the... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed 3 weeks ago
    This was easily the best self check-in accommodation we encountered during our two week stay in Florida. The owner has thoughtfully created a beautiful, airy and spacious one...
    5 of 5 bubbles Reviewed 3 weeks ago
    Mario's accommodations are cozy , comfortable and clean. Mario is very friendly and professional. He made himself available to us via cell phone for any questions or concerns. He...
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    1 / 15
    5 of 5 bubbles (4) Excellent
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 4 | Quick View
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    • Washer
    • Air Conditioning
    • DVD Player
    • Porch
    • Balcony
    • Parking
    • Outdoor Dining Area
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    Upper Duval is the best! A few steps away from the Southernmost pt & beaches,great restaurants,art galleries, Louies backyard,and Blue Heaven. A few more steps from Mallory sq, Sloppy Joes, Smokin tuna, the pier restaurants, entertainment day and night. Have the best of both worlds, be in the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed March 9, 2016
    First time renting from Trip Advisor. The entire process went very smooth & would definitely recommend it. Stayed at this location for a week with spouse and another couple...
    5 of 5 bubbles Reviewed March 18, 2015
    Wonderful location. Delightful owners. Relaxed and comfortable. Pool area great...sun if you want it and shade if you need it. Would definitely recommend to friends and will stay...
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    1 / 12
    5 of 5 bubbles (3) Excellent
    Duck Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Hot Tub
    • DVD Player
    • Waterfront
    • Wi-Fi
    • Washer
    • Ocean Views
    • Patio
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    SPA VILLA ON BLUE WATER CANAL ASK ABOUT OUR DECEMBER & JANUARY RATES Nestled within the charming island resort of Hawk's Cay Escape to your very own Tropical Paradise in the heart of the Florida Keys. Although we are not affiliated with Hawks Cay Resort the Marina, Spa, Dolphin Facility,... View all property information
    Location Information
    Duck Key, Florida Keys 33050
    5 of 5 bubbles Reviewed 4 weeks ago
    I was so happy to find this gem available during spring break only 3 days prior. I brought my 5 kids down with me. The villa was nice and clean with a view of the water in back...
    5 of 5 bubbles Reviewed May 24, 2016
    This is a great place to spend a week. The unit is clean with a beach decor, accommodating four adults with no problem. The location is half way down the Keys so it was not too...
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    1 / 24
    5 of 5 bubbles (1) Excellent
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 6 | Quick View
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    • Washer
    • Satellite TV
    • DVD Player
    • Ocean Views
    • Parking
    • Patio
    • Air Conditioning
    • Internet Access
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    2 Bdrm, 1 Bath, Washer/dryer, Dishwasher, Great Porch View Of Southard St, Pool<BR><BR>Multiple week and military discounts available. Great Fall rates! Queen bed in Master Bedroom, two single beds in second bedroom, fold out queen bed in couch, gated back patio with gas grill, lounge chairs, table... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed July 14, 2016
    Condo was ideally located for all our activities. Very comfortable and enjoyable! Cindy was a pleasure to work with, can't wait to return to Tiki, Too!
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    1 / 30
    5 of 5 bubbles (7) Excellent
    Marathon
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Ocean Views
    • DVD Player
    • Wi-Fi
    • Satellite TV
    • Washer
    • Hot Tub
    • Waterfront
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Come to the Florida Keys and enjoy living in luxury at 'Blue Heaven'. There are blue skies, crystal clear blue water, calm tropical breezes at 'Blue Heaven' every day. This beautiful new three bedroom, three bath villa has 2,000 square feet on 2 levels with under cover parking. It is located in the... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed July 27, 2016
    I stayed in this condo for a week with my 3 children (ages 12, 19, and 20) and a friend and her child (age 20). The condo was located near all that we wanted to explore in...
    5 of 5 bubbles Reviewed November 23, 2014
    Really enjoyed this home, clean,secure, owner answered all questions in a timely fashion. Highly recommended!
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    1 / 15
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • DVD Player
    • Air Conditioning
    • Balcony
    • Wi-Fi
    • Washer
    • Satellite TV
    • Hot Tub
    • Private Outdoor...
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Take a dip in our gorgeous new pool, or jacuzzi (for 14 people)! Ocean Pointe Suites in Key Largo is an all-suite resort located directly on the Atlantic Ocean. Our 60 acres in the Florida Keys are part of a protected mangrove forest, entered through a private gatehouse and road. The suite offers a... View all property information
    Location Information
    Tavernier, Key Largo 33070
    1 / 22
    5 of 5 bubbles (3) Excellent
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Hot Tub
    • Air Conditioning
    • Outdoor Dining Area
    • Parking
    • Wi-Fi
    • Balcony
    • Washer
    • Grill
    Suitability
    • Pet-friendly
    • Child-friendly
    • ?
    • Smoking allowed
    • x
    About this property
    This 2 bedroom, 2 bathroom unit offers all the convenience and comfort of your own home. It is spacious and fully equipped. Located just minutes from Smathers Beach, two miles from Higgs Beach.<BR>This condo is a fourth floor unit (there are two elevators in the building). It has a private balcony... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 25, 2017
    Found Key West absolutely enchanting, and this little condo was in a perfect location to get to the hustle and bustle of downtown Key West, but be able to retire to a quieter...
    5 of 5 bubbles Reviewed November 22, 2016
    Lovely clean condo with great views of the salt ponds. Fully equipped with everything you need. Great having a supermarket on site too.
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    1 / 32
    4.5 of 5 bubbles (3) Very good
    Key West
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Parking
    • DVD Player
    • Washer
    • Internet Access
    • Patio
    • Satellite TV
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • Smoking allowed
    • x
    About this property
    Coral Hammock was built in 2004. Casa Paradiso is a spacious 3 bedroom, 3 bath home in a beautifully landscaped gated community. It features 2 king size beds and one queen.The kitchen is fully equipped with modern appliances, dishes and cooking utensils.There is an outdoor grill. There is a brand... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed March 7, 2017
    The townhouse on Stock Island (Key West) met all of our needs. It was clean, roomy and convenient. Having 3 full baths was a real plus for 6 women. The pool was delightful...
    5 of 5 bubbles Reviewed November 12, 2016
    House was very clean and the owner was very helpful and responsive. I would definitely stay again and would highly recommend it to anyone going to key West !
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    1 / 23
    5 of 5 bubbles (5) Excellent
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Wi-Fi
    • Washer
    • Satellite TV
    • DVD Player
    • Hot Tub
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    The newly renovated oceanfront condo is located in Tavernier Key, a community situated along the southern border to Key Largo. The grounds encompass over 60 acres and is situated in a tropical paradise surrounded by mangrove forest, coconut trees and the pristine turquoise waters of the Florida... View all property information
    Location Information
    Tavernier, Key Largo 33070 3100
    5 of 5 bubbles Reviewed 4 weeks ago
    This is a very nice condo and very adequate for 4 people although you can't get more than 2 people on the balcony at one time. It is pretty small but does look right out at the...
    5 of 5 bubbles Reviewed July 9, 2016
    I started looking for a place to stay for 10 days, the hotels were way to expensive. I happen to stumble upon Ocean Pointe in Tavernier Fl. I rented a timeshare,I didn't book...
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    1 / 39
    4.5 of 5 bubbles (16) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Air Conditioning
    • Parking
    • Internet Access
    • Grill
    • Patio
    • Satellite TV
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • ?
    • Smoking allowed
    • x
    About this property
    Located at Papa's Hideaway, the serene grounds strike you immediately upon entering the beautifully landscaped, gated property. Located just one block off World Famous Duval Street, Garden of Eden is the perfect combination of quiet Key West living and optimum access to all of the islands best... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed September 10, 2015
    Beautifully decorated Old Key West home. Our kids (12, 5) loved seeing the Iguana in the courtyard. The pool was nice to relax in after a day of sightseeing. Beds were...
    5 of 5 bubbles Reviewed September 9, 2015
    We brought my daughter, her best friend, and her boyfriend to Key West to celebrate her 21st birthday. The pool was a welcome retreat from the heat and the pub crawls. The...
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    1 / 25
    Cudjoe Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Waterfront
    • Satellite TV
    • DVD Player
    • Washer
    • Patio
    • Wi-Fi
    • Parking
    • Air Conditioning
    Suitability
    • Pet-friendly
    • Child-friendly
    • x
    • Smoking allowed
    • x
    About this property
    Venture Out Unit 411 is a waterfront unit with 35' of dock space and Wi-Fi internet access that will provide you with all of the comforts of home. Rather than be cramped into a simplistic motel room, you'll have all of the benefits of having a kitchen, dining room, living room, two bedrooms, two... View all property information
    Location Information
    Cudjoe Key, Florida Keys 33042
    1 / 25
    5 of 5 bubbles (40) Excellent
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • Waterfront
    • Air Conditioning
    • Ocean Views
    • Parking
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    • Pet-friendly
    • Child-friendly
    • x
    • x
    • Smoking allowed
    • x
    About this property
    BRAND NEW WHISPER QUIET $5300/42,000 BTU'S TRI-ZONE AIR CONDITIONING/HEATING SYSTEM PROFESSIONALLY INSTALLED AND COMPLETED IN MAY 2014. Simple and unpretentious, the Oceanfront Bungalow Hideaway is a mobile home located right on the water at Boot Key Harbor. Only 45 miles south to Key West. One... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed November 10, 2016
    My Wife and I, My daughter and her Husband, we had a Great time there, the place was clean, and there were no dissatisfaction there, we plan to go there again, the owner Bill C...
    4 of 5 bubbles Reviewed June 19, 2016
    Bill the owner of the Property was excellent to deal with and answered all questions promptly regarding the property and surrounding areas . The Property was exactly as as...
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    1 / 52
    5 of 5 bubbles (14) Excellent
    Key West
    5 Bedrooms, 4 Bathrooms, Sleeps 16 | Quick View
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    About this property
    Almost Southernmost Retreat is made up of ALMOST SOUTHERNMOST and ALMOST SOUTHERNMOST TOO on the 400 block of Truman Avenue is the perfect location between Duval Street and Whitehead Streets. This style is common throughout the islands. Located in a row of identical cigar-maker cottages, the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed January 1, 2015
    Three generations, nine people, stayed here over Christmas. We each had space to be by ourselves, and we all had space to get together. Nine of us sat around the table in the...
    5 of 5 bubbles Reviewed September 3, 2014
    I came to the Almost Southernmost Retreat for my friends bachelorette party for Labor Day weekend 2014. We had 12 girls and there was more than enough room for everyone. This...
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    1 / 33
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Tropical Village Cottage - is a two bedroom, two bath vacation cottage that overlooks a large shared seasonally heated pool, sun-deck and pool-side grilling station. With all the amenities of contemporary living set in island style and decor. Tropical Village Cottage is your ticket to a stress free... View all property information
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    Key West, Florida Keys 33040
    1 / 14
    4.5 of 5 bubbles (8) Very good
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Large 3 Bedroom, 2 Bath OCEANFRONT condo. Breathtaking views of the Atlantic from every room. Tropical landscaped property with large heated pool and Jacuzzi. Just steps to Smathers Beach which has swimming, jet skis, parasailing, etc. Fully appointed condo with all the amenities of home at... View all property information
    Location Information
    Key West, Florida Keys 33040
    4 of 5 bubbles Reviewed February 9, 2015
    Loved the condo! Besides a few minor issues the place was everything it promised and more. Nicely and comfortably decorated with lots of room (there were 6 adults). The balcony...
    5 of 5 bubbles Reviewed December 29, 2014
    The condo comfortably fit out family of 5. It had lovely ocean views, homey updated decor, a pool & jacuzzi, while walking distance to Smather's Beach equipped with all kinds of...
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    1 / 24
    4 of 5 bubbles (16) Very good
    Islamorada
    2 Bedrooms, 2 Bathrooms, Sleeps 4 | Quick View
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    This is a neat house! It sits right on the ocean with a large yard (by keys standards!). Very nicely landscaped (hibiscus, palm trees, tall pine trees, green grass)with statues from all over the world. Very private with a big gate. The house is decorated with pictures taken from all over the world... View all property information
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    Islamorada, Florida Keys 33036
    4 of 5 bubbles Reviewed January 11, 2014
    Location, location, location; this home was a great getaway, and beautifully landscaped (but not manicured) with older Australian pines, sea grape, palms and silver buttonwood...
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    1 / 17
    5 of 5 bubbles (1) Excellent
    Marathon Shores
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Hideaway By the Sea is located in a small, quiet complex (Gulfpointe II) with only 20 units, tucked away on a private peninsula that juts into the Gulf of Mexico. Located on the islands of Marathon in the heart of the Florida Keys, Key Largo is about 50 miles north, Key West is about 50 miles... View all property information
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    Marathon Shores, Marathon 33050
    5 of 5 bubbles Reviewed March 13, 2017
    Felt just like home, decorated beautifully. Very responsive owners. There's nothing like a getaway to the Florida Keys. We miss Hideaway by the Sea already and can't wait to...
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    1 / 33
    4.5 of 5 bubbles (3) Very good
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • Pet-friendly
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    • x
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    About this property
    Welcome to your home away from home! “Bel Cielo” is a beautiful two-story condo in the quaint community of Moon Bay, located at mile marker 104 in Key Largo. (Moon Bay was recently featured on HGTV's Beach Front Bargain Hunt!) Featuring 1,146 square feet of living space with handsome furnishings,... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed August 20, 2015
    The condo is beautifully decorated. Furniture is gorgeous and functional. Love the local photos throughout. The location of the condo inside Moon Bay is wonderful. Literally...
    4 of 5 bubbles Reviewed August 11, 2014
    Bel Cielo is nicely furnished and well maintained. An abundance of bath and beach towels is included and the kitchen is fully equipped. The owner responded promptly to questions...
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    1 / 25
    5 of 5 bubbles (4) Excellent
    Key West
    3 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    Toon Hall: World-class comfort, lush tropical surroundings and unmatched privacy characterize the former winter home of Pulitzer Prize winning cartoonist, author and artist, Jeff MacNelly. Designed to accommodate a large family or group, this three bedroom home has two full baths plus the... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 21, 2016
    We rented the entire compound for our wedding, please see my review on Tropical Village for more information. I did not stay in this cottage but our guests had rave reviews and I...
    5 of 5 bubbles Reviewed March 5, 2015
    My family and I stayed at Toon Hall the last week in February and had a blast. The home is located close to Higgs Beach, a few blocks away, and a few blocks from Duvall St. The...
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    1 / 10
    5 of 5 bubbles (9) Excellent
    Big Pine Key
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    This 2 bedroom 2 bath ground level home with a glassed in Florida room, is on a boating canal with only 1/4 mile to open water. In five minutes at idle speed you have immediate access to the Atlantic or the Gulf of Mexico via Bogie Channel. The Canal has 50 feet of concrete seawall with bumpers... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed November 20, 2016
    My hubby and I along with sister and bro-in-law had the best time. This cottage is quaint and very clean and has everything you could possibly need. They thought of everything...
    5 of 5 bubbles Reviewed July 11, 2016
    We rented this house from Captain Ron and had a great time. We brought a boat and were able to dock it in the canal with no problems. The house was outfitted with everything we...
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    1 / 30
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    About this property
    This gorgeous two bedroom, one bathroom property is located in one of the most desirable areas of downtown Key West. With it's lavish walkways, on-site pool and private parking, you will be able to relax and enjoy being in the heart of it all. Take a stroll to Duval Street or to the beach; both... View all property information
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    Key West, Florida Keys 33040
    1 / 19
    4 of 5 bubbles (10) Very good
    Marathon
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
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    About this property
    Located in the centre of Marathon. This destination is perfect for discovering the beautiful Florida Keys. One hour's drive from Key West or Key Largo. Marathon is famous for the sportfishing including but not limited to Marlin, Sailfish, Mahi-Mahi and there are numerous places to rent a boat,... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed October 7, 2015
    My husband and I rented the condo for one week and enjoyed our stay. We'll rent again when in the Keys. PROS: Owner is friendly, responsive, and the rental process was simple...
    3 of 5 bubbles Reviewed July 29, 2015
    I've been going to Sombrero Resort for many years now and am sad to see what has been happening to it. While at one time it was a resort, it has now become resort/condo. Many...
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    1 / 28
    4.5 of 5 bubbles (23) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    About this property
    Lush and tropical gardens surround this beautiful development in the heart of historic Old Town. Private, secured parking beneath the complex and security entrances gives the feeling of exclusivity unparalleled in Key West. The foyer of this Mediterranean Style unit with Mexican Tile downstairs... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed April 7, 2015
    Very well decorated an equipped with everything needed. Nice open area, the pictures do not do it justice. Larger living area and dining than the photos show. Two nice balconies...
    5 of 5 bubbles Reviewed August 6, 2014
    Excellently furnished, Immaculately clean. Completely up to date appliances and amenities. (Washer & dryer just off the kitchen!) Tip-Bring your own laundry detergent Traveled...
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    1 / 18
    5 of 5 bubbles (1) Excellent
    Marathon Shores
    6 Bedrooms, 3 Bathrooms, Sleeps 12 | Quick View
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    • x
    About this property
    This private vacation home is situated at a great location close to the middle of Marathon with just a lovely short walk or bike ride to the famous Sombrero Beach. 6 bedroom/ 3 bathroom with comfortable and inviting coastal designed decor. Attention to detail with fine linens and beach towels. 2... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 27
    4 of 5 bubbles (4) Very good
    Tavernier
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    Travelling with your family or friends and want to stay all together? Prefer to cook by yourself while on the vacation? Or maybe you just want to feel yourself like home, not like in a hotel. If you have many people in your party, or big family, or want to have some privacy from your friends or... View all property information
    Location Information
    Tavernier, Key Largo 33070
    5 of 5 bubbles Reviewed March 1, 2017
    For the money the apartment we had was perfect. The location and the amenities were unbeatable. We definitely plan to return soon!
    3 of 5 bubbles Reviewed January 30, 2017
    Ocean Point is a great resort located just south of Key Largo. The resort is located to all restaurants and local attractions. The grounds are well maintained and secure...
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    1 / 6
    4.5 of 5 bubbles (6) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Escape to Key Largo's ultimate weekend or vacation getaway ~ the best Inn in the Florida Keys. Located directly on the Atlantic Ocean, in unspoiled Largo Sound. Offering the best access to the finest of Florida Keys charter fishing, Everglades's excursions, Eco-tours, snorkeling and scuba diving.... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed February 10, 2017
    My husband and I reserved a suite on the ground floor which was both convenient and lovely. The Inn was a quiet oasis minutes from Pennekamp state park and was just what we were...
    5 of 5 bubbles Reviewed June 5, 2015
    one of the nicest place&staff i have ever rented hope to go back soon and visit gilda & crew DANNY&SHIRLEY TRY IT YOU WILL LIKE IT DANNY
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    1 / 17
    5 of 5 bubbles (10) Excellent
    Big Pine Key
    3 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • x
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    About this property
    REEL PARADISE, located in Big Pine Key, Florida Keys offers a large open format Keys retreat with vaulted ceilings. 3 bedrooms – King bed master suite – Queen bed master suite and two full beds in a spacious third bedroom, 3 baths, large kitchen, dining room, family room, sitting area, large... View all property information
    Location Information
    Big Pine Key, Florida Keys 33043
    5 of 5 bubbles Reviewed March 13, 2017
    Very nice house.Everything is kept immaculate.The house is very roomy and well stocked.The grounds are beautiful.There is a nice spot to relax or cookout by the canal.The owner...
    5 of 5 bubbles Reviewed August 5, 2015
    This is a great place to enjoy the lower keys. Extremely clean and well appointed. We stay there as often as we can. I can't wait to go back.
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    1 / 28
    Marathon Shores
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • x
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    About this property
    The "Mermaid House" sits directly on the ocean with the unobstructed views, gorgeous sunrises and some of the best boating access in the Marathon area. House offers 4 Queen Bedrooms and 2 full bathrooms. 3 bedrooms and a bathroom are located on the ground level. Upstairs is the Queen Master bedroom... View all property information
    Location Information
    Marathon Shores, Marathon 33050
    1 / 13
    5 of 5 bubbles (2) Excellent
    Key Largo
    3 Bedrooms, 3 Bathrooms, Sleeps 8 | Quick View
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    • Central Heating
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    • Pet-friendly
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    • x
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    • x
    About this property
    THE MOON BAY PENTHOUSE located beautiful Key Largo. This beautiful Penthouse condo is on the Florida Bay side of Key Largo at Moon Bay Condos just one mile from John Pennekamp State Park. The Penthouse condo is 1 of 2 original, top floor, large Penthouse units that includes 2 parking garages that... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    5 of 5 bubbles Reviewed 4 weeks ago
    This is a large condo on a top floor in the complex that is at the very beginning to FL Keys (MM 104) in Key Largo. Plenty of room for a large family, big enclosed terrace, each...
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    1 / 33
    Key West
    4 Bedrooms, 2 Bathrooms, Sleeps 10 | Quick View
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    • ?
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    • x
    About this property
    Welcome to "Duval Street Retreat" - The perfect vacation rental for large groups looking to be around all the Duval St action! Duval St. Retreat consists of two separate two-bed, one-bath condos located at 1124 Duval St. The property is only a couple steps (or stumbles) away from fine dining,... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 27
    4.5 of 5 bubbles (21) Very good
    Key West
    2 Bedrooms, 3 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    The beaches of the Atlantic Ocean are less than a 7 minute walk away. This ultra luxurious 2 bedroom, 2-1/2 bath, 2 story house has been totally redecorated by one of Key West’s most talented designers, Michael Pelkey. Sitting in a row of 6 townhomes built by Key West's premier builder, Island... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed December 11, 2014
    It was our first time in Key West and, well, you just never know. I got this one spot on though. The decor is fun. the kitchen is very functional. The two master suites were...
    5 of 5 bubbles Reviewed October 25, 2014
    The townhouse is excellent. Location is also a huge positive. Clean and updated. Wifi was easy to access.
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    1 / 36
    4.5 of 5 bubbles (14) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • ?
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    • x
    About this property
    This house is in a quiet residential neighborhood where loud boisterous parties are not appropriate. This 2 bedroom, 2 bath, 2 story house has an open floor plan featuring lots of pine walls and floors throughout. Upstairs is the king bedroom and a full bath and downstairs is the second bedroom... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed November 9, 2014
    We were very happy with this house rental. The pictures only hold a small window into this gem. Walking distance to Duval (although a cab was only $6 if needed). Great living...
    3 of 5 bubbles Reviewed August 12, 2014
    Pros - charming cottage, two bathrooms, private pool, dish washer, washer and dryer, nice bed and linens, just a few blocks from Duval, plenty of street parking. Cons - across...
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    1 / 13
    4.5 of 5 bubbles (2) Very good
    Marathon
    1 Bedroom, 2 Bathrooms, Sleeps 4 | Quick View
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    • Pet-friendly
    • Child-friendly
    • x
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    • x
    About this property
    This condo has full resort amenities: Marina with boat dockage, heated pool, tennis & basketball courts, bicycles, canoes, kayaks, paddle boats, tiki huts with picnic tables & charcoal grills, security and wifi. Waterfront to the beautiful Gulf of Mexico, parking for boat trailers, with plenty of... View all property information
    Location Information
    Marathon, Florida Keys 33050
    4 of 5 bubbles Reviewed January 31, 2017
    The unit was beautifully decorated and we were comfortable there. The Gulf view was great, right out our door. The other people were friendly and everyone seemed happy to be...
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    1 / 12
    4.5 of 5 bubbles (17) Very good
    Key West
    2 Bedrooms, 2 Bathrooms, Sleeps 5 | Quick View
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    • Pet-friendly
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    • x
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    • x
    About this property
    Tropical 2 bedroom, 2 bath Key West Condo. Large balcony overlooking pool. Full kitchen and living room with all the amenities of home. Large heated pool and Jacuzzi. Tennis court and gym. Washer and dryer in unit. Great condo complex on quiet side of island. Located 1 mile from Smathers... View all property information
    Location Information
    Key West, Florida Keys 33040
    5 of 5 bubbles Reviewed 3 weeks ago
    The place was very nice and clean. There were plenty of blankets, pillows, towels, etc. The breeze was fantastic. The balcony was secluded enough that I didn't feel like people...
    5 of 5 bubbles Reviewed October 25, 2016
    Really enjoyed my stayed, I Will definitely will stay hear again, everything was just as expected, location was great, owner was fantastic and very helpful, apartment was very...
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    1 / 35
    Key West
    2 Bedrooms, 1 Bathroom, Sleeps 4 | Quick View
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    • x
    About this property
    Truman at Duval - if you're looking for South Beach slick-- not here! If you're looking for Key West charm and location, look no further. Small 2 bedroom, 1 bath, apartment that just screams fun and good times! Duval, with its world class reputation, beckons you to come play. Sight-seeing, people... View all property information
    Location Information
    Key West, Florida Keys 33040
    1 / 43
    4 of 5 bubbles (1) Very good
    Key Largo
    1 Bedroom, 1 Bathroom, Sleeps 3 | Quick View
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    • Pet-friendly
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    • x
    • x
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    • x
    About this property
    This 1 Bedroom Apartment is located upstairs overlooking direct views to Florida Bay. It is furnished in white with tile floors, air conditioning, WIFI, cable Television with 75 channels. Linens are provided and the kitchen is fully stocked for cooking. You have private door step parking and can... View all property information
    Location Information
    Key Largo, Florida Keys 33037
    4 of 5 bubbles Reviewed 3 weeks ago
    We enjoyed our stay at this Key Largo RV Park. The accommodation was a wee bit dated but nevertheless quite comfortable and very clean. The apartment is spacious with all the...
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    1 / 20
    5 of 5 bubbles (6) Excellent
    Marathon
    3 Bedrooms, 2 Bathrooms, Sleeps 6 | Quick View
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    • Ocean Views
    • Air Conditioning
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    • Pet-friendly
    • Child-friendly
    • ?
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    • x
    About this property
    Stay at our Marathon Key Vacation Rental House in the heart of the Florida Keys. Vacationers find great tarpon, dolphin, sailfish, and snapper fishing, coral reefs and wrecks for scuba diving. Marathon is situated at the mid-point of the Florida Keys island chain, which is why locals have declared... View all property information
    Location Information
    Marathon, Florida Keys 33050
    5 of 5 bubbles Reviewed August 8, 2016
    The house was spacious and comfortable. Beaches, restaurants, grocery stores, etc. were all a short drive from the house and easy to get to. The rental is a good value for the...
    5 of 5 bubbles Reviewed July 15, 2016
    We mostly fished. This house had an amazing ocean access. Quiet area. Tarpon rolling in canal. Bait just outside canal. Close to anything in town you need. Will be staying here...
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