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Pet Friendly Holiday Rentals in Key West

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    Travellers to Key West are booking December dates now. Secure your holiday rental today, and have the perfect trip.
    63 Matching Rentals in Key WestView all 370 rentals
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    LA DOLCE VITA, OLD TOWN!!  STEPS TO DUVAL!! SLEEPS 2-4, 3 BLOCKS TO SOUTH BEACH!1 / 27
    (5)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    New Listing Family Friendly1 / 32
    (3)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Summer Blow Out! $300 off. Tiki Too Townhouse, 2 blocks from Duval,Pool, Bikes1 / 24
    (3)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 1 Bathroom, Sleeps 5 Quick View
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    • Secure Parking
    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A great place to stay and play near the water and Old Town Key West! Located in Truman Annex, a secure enclave of historic and exclusive residences, Truman Annex is the most exclusive and magnificent development in Old Town Key West with wide streets lined with multi-million dollar homes that are...
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    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 1 Bathroom, Sleeps 5
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    5 Bedrooms, 3 Bathrooms, Sleeps 18 Quick View
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    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Private Garden
    • Parking
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    While relaxing in the free form lagoon pool, the surrounding scenery makes you feel like you are on your own deserted island. Upon entering the 3200+ square foot home, the spacious nature of the home is evident providing ample room for large groups. Around the back of the home, the large deck with...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 3 Bathrooms, Sleeps 18
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    Luxury Rental Old Town Key West Close to Beach. Private Heated Pool1 / 22
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Garden
    • Wi-Fi
    • Satellite TV
    • Secure Parking
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    Beautiful property. This house was stunning, thank you so much for letting us stay there. All amenities were provided. I love all the plants and trees surrounding the pool and...
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    About this property
    Beautiful Keywest home blocks from Higgs Beach, playgrounds, restaurants, and famous Duval street. This rental includes use of 2 beach cruisers. Private Pool and front yard. Tropical Oasis. Includes washer and dryer. This is a beautiful Key West home in old town. All amenities included.
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Grill
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Satellite TV
    • Housekeeping Included
    • Patio
    • Washer
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    2017 Historic Preservation Award Winner! This licensed vacation home was recently featured on Key West's historic home tour and is available to rent monthly. We recently completed a massive 6-month remodel, making this one of the more spectacular vacation homes you'll find for rent in Old Town. In...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Catamaran CALYPSO with Summerallthetime Sailing Co1 / 31
    (12)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Secure Parking
    • Air Conditioning
    • Ocean Views
    • Waterfront
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 April 2017
    We had the pleasure to sail around the Florida Keys on the Calypso last month. The boat was great and very well kept. Beds were comfortable and cabins felt clean and polished...
    Reviewed 28 March 2017
    Capt John took our family of 4 on an ultimate Spring Break Keys journey!The sailboat is well equipped and very clean and modern. We had plenty of room to rest and play on...
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    About this property
    The Beautiful 42' Catamaran Calypso is a spacious Luxury Boat with all the latest Amenities. With 3 Cabins available... it sleeps 6 people comfortably. Each cabin has its own bathroom with all new faucets and electric flush toilets. Aboard Calypso you will find several places to lounge, sit back,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Patio
    • DVD Player
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This fully furnished turn-key two bedroom bungalow is the perfect spot to escape the winter weather in tropical Key West! Full kitchen, luxury shower, high ceilings and washer/dryer in unit! Also has a nice little fenced in outdoor space with a picnic table for enjoying the beautiful weather in the...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Waterfront
    • Grill
    • Patio
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This private ground floor waterfront home is located in the Key Haven subdivision of fine homes. Beautifully decorated with all new furniture, new flat screen televisions, new beds that includes two king size for extra comfort, large open living room with french doors invites in the tropical...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    Sailboat Camping 4 The Adventurous!1 / 15
    (1)Terrible
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Rosie is at anchor in harbor just off the bustling downtown life of Key West. She has a very comfortable queen size V berth bed, a cozy saloon (living room) great for curling up, amazing sunset views, and in a very friendly neighborhood of boats! Rosie is a 33ft Pearson Sloop anchored only a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    3 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    • Secure Parking
    • Air Conditioning
    • Private Garden
    • Satellite TV
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful home in the desirable canal front community of Key Haven. At the end of a quiet street this 3/2 home features a 2010 renovated kitchen, gorgeous enclosed back porch for relaxing, 2 boat lifts on the canal. The home is set deeply off the street for privacy, and has a long driveway for 2+...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 8
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    5 Bedrooms, 5 Bathrooms, Sleeps 14 Quick View
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    • Air Conditioning
    • Satellite TV
    • Wi-Fi
    • Private Garden
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    KEY WEST MANSION - Incredible 3-Story Mansion W/ Private Beach, Pool, & Spa This KEY WEST MANSION is 'Grande' to say the least. With unspoiled views from every angle, to playful colors, and unrivaled decor and design, this home is a Chateau unlike any other. This Chateau is designed in true keys...
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    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 14
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    3 Bedrooms, 3 Bathrooms, Sleeps 8 Quick View
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    • Washer
    • Internet Access
    • Air Conditioning
    • DVD Player
    • Patio
    • Grill
    • Satellite TV
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Our Old Town Eyebrow has an ideal location on the island of Key West! Only 1 1/2 blocks from the famous Duval Street but set back in a quiet, comfortable neighborhood for you to enjoy your time with loved ones. Stunning views of the Key West Light house greet you as you enter our home. The unique...
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    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 8
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    Seaside Condo $1750-$2500 mon. Spring-Summer-Fall1 / 17
    (2)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Outdoor Dining Area
    • Shared Outdoor Pool (Unheated)
    • Wi-Fi
    • Satellite TV
    • Terrace
    • Air Conditioning
    • Secure Parking
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 March 2016
    This apartment was the perfect place to experience Key West, it was sunny and quiet, right across the street from the beach and just minutes away to Old Town with it's great...
    Reviewed 12 March 2016
    This Key West getaway condo is a wonderful escape from the freezing temperatures of the northeast. I was here other years and noticed this time that there is a beautiful new...
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    About this property
    This delightful sunny, quiet apartment is located across the street from Smathers beach and just a ten minute drive to Old Town. The apartment is set in a large lush tropical garden with two Olympic size swimming tools, tennis court, shuffle board court and outdoor lounging and dining areas, It is...
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    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Key West Condo 2 br, 2ba - ocean veiw from balcony1 / 12
    (7)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Hot Tub
    • Air Conditioning
    • Private Outdoor Pool (Heated)
    • Patio
    • Grill
    • Washer
    • Satellite TV
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 January 2017
    Very nice condo overlooking the Key West airport. The unit has covered parking. There is a pool and tennis court. Bikes can be rented form real estate group that manages the...
    Reviewed 27 October 2016
    Very nice condo, I will rent it again next time. With a covered parking spot. Convenient to everywhere. Close to the beach and a nice pool.
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    About this property
    The resort all the convenience and comfort of your own home with these spacious fully equipped 2 bedroom condos located just minutes from Smathers Beach and 2 miles from Key West Airport. This location is also two miles from popular Higgs Beach and between 4 miles from the Key West Lighthouse...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    4 Bedrooms, 4 Bathrooms, Sleeps 10 Quick View
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This three story, elegant home has something for everyone! It is located three blocks from Duval Street and two blocks from the historic Key West Seaport. There are three bedrooms on the second floor and a third floor suite with living room, efficiency kitchen, bedroom and full bathroom. There is...
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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 10
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    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Ocean Views
    • Wi-Fi
    • Waterfront
    • Air Conditioning
    • Patio
    • Satellite TV
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This is for the guest that would like to experience the yachting lifestyle without ever leaving the dock. Staying at the dock allows you to come and go as you please whether it be scootering around Wilmington town or shopping, eating and drinking your way down to the board walk on front street ....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    The Tree House Old Town 2 Bedroom MONTHLY Rental1 / 12
    (5)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 7 Quick View
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    • Grill
    • Air Conditioning
    • Porch
    • Outdoor Dining Area
    • Balcony
    • Wi-Fi
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 9 January 2017
    The Tree House is appropriately named, tucked away on quite street a couple blocks off fun and busy Duval, the windows open wide, right into the canopy of mature trees, as does...
    Reviewed 19 October 2016
    I am a 31 yr old entrepreneur that can work from anywhere and was looking to escape from the brutal New Jersey winter we were having. So I booked a the entire month of March in...
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    About this property
    Our lovely home is rented for a 28 day minimum.Enjoy the lovely Key West ocean breeze from your private Tree House. Two Blocks to Blue Heaven, 4 blocks to the beach, 3 blocks to Duval, 3 blocks to the biggest pool on the Island, you will not find a better or quieter location to enjoy all that Key...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 7
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    Mermaid Cove- A small compound- Sleeps up to 121 / 28
    (10)Average
    4 Bedrooms, 4 Bathrooms, Sleeps 12 Quick View
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    • Balcony
    • Washer
    • Outdoor Dining Area
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2015
    If you want to experience Key West like the locals do, then Mermaid Cove is for you. Quaint hideaway in the midst of historic Key West close to shops and few restaurants Mermaid...
    Reviewed 19 October 2014
    We met up at Mermaid Cove with my sister's family to celebrate our nieces college graduation. The perfect setting for young adults! For the parents, it was just fun seeing our...
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    About this property
    Mermaid Cove is a small island compound that is great for large groups or big families. It's made up of 2 apartments and 2 cottages with an intimate courtyard in the middle with BBQ grill and table, shaded by a massive mango tree. Located right on Duval Street, Mermaid is just a block and a half...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 4 Bathrooms, Sleeps 12
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Parking
    • Satellite TV
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    A convenient hideaway for your Key West and Lower Keys adventures, this two-bedroom condo is tucked into a quiet complex near shopping, bars, live music, beaches, and Mallory Square. Cozy, fully-appointed rooms include everything you'll need for your Key West vacation but your own clothes. With...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Mango Hideaway-King Suite just steps off Duval St1 / 18
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Patio
    • Grill
    • Private Garden
    • Wi-Fi
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 6 May 2017
    The Mango Hideaway is a nice spot in the middle of Old Town. Walking distance to everything. Private patio and entry off of the side street are a plus. Great location and a...
    Reviewed 4 March 2017
    We had a great time in Key West staying in the Mango Hideaway!Very private and comfortable yet only a minutes walk to Duval street.Also centrally located in old town so seeing...
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    About this property
    Mango Hideaway is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local as...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Conch Haven Old Town 1/1 MONTHLY Rental1 / 12
    (1)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Satellite TV
    • Patio
    • Washer
    • Hot Tub
    • Air Conditioning
    • Internet Access
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 28 November 2016
    This property is very convenient to everything in Key West. We walk every day--we can go to the beach, the sunset, Duval, and all of the various attractions on foot. The...
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    About this property
    This 1200 sq ft luxury apartment in the the heart of Old Key West is located only 2 blocks off Duval St and is a short walk or bike to all the fun of Key West ! Very quiet street with no through traffic. The property is completely private and safe, surrounded by a 6 foot gated fence and tropical...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Terrace
    • Air Conditioning
    • Satellite TV
    • Internet Access
    • Washer
    • Patio
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautifully renovated duplex in Old Town. 2 bed/1.5 bath. Sleeps 4-6. There is a private stairway to apartment/loft upstairs. Upstairs unit is a massive 1100 sq ft with cathedral ceilings and loft (2nd bdrm). There is a king bed in the master, full bed in the loft and a pull-out sofa. Fully...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Hot Tub
    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    New owners and wide open availability! It is not too late to come to Key West! Key West Casablanca Too is the perfect get-a-way vacation rental for two! Casablanca Too is one half of an impeccably maintained duplex that is located on the edge of the Meadows and Historic Old Town. This is a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool1 / 28
    (2)Excellent
    4 Bedrooms, 3 Bathrooms, Sleeps 7 Quick View
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    Amenities & Details
    • Air Conditioning
    • Washer
    • Private Outdoor Pool (Heated)
    • DVD Player
    • Internet Access
    • Satellite TV
    • Grill
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    Such a wonderful and comfortable home. We were steps away from Duval street but it was so quiet at night. The pool was a great way to relax after a long day of walking and...
    Reviewed 4 December 2016
    Very nice clean Bungalo. Close to Dival walking distance from everything In old town. My only minor complaint is that the barbecue pit was absolutely filthy. I spent a lot of...
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    About this property
    The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The charm and historic features have been retained, while all the luxuries of today have been added. There is a master bedroom, with king bed and full bath, on the first floor. Additionally, there is a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    Hyatt Beach Club1 / 17
    (1)Very good
    2 Bedrooms, 5 Bathrooms, Sleeps 6 Quick View
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    • Ocean Views
    • Shared Outdoor Pool (Unheated)
    • Washer
    • Hot Tub
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 29 January 2016
    I own at this hyatt timeshare. The units are spacious. Very clean and nice grounds. Only problem is away from downtown and car is needed. Hyatt working on new shuuttle service...
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    About this property
    This property is located on the north side of Key West 4 miles from downtown.It is available from Dec. 27th to January 3rd. A great venue for the holiday season. This is a great two bedroom two bath unit with master bedroom and en suite. Private balcony which overlooks outdoor infinity pool. Also a...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 5 Bathrooms, Sleeps 6
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    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    • Internet Access
    • Balcony
    • Terrace
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This unit offers the perfect way to visit Key West, park your car and walk everywhere. Sunset celebration is only steps away. This town home is complete luxury with viking appliances, custom kitchen cabinets, granite counter tops, beautifully furnished, and Westin Hotel heavenly beds. The amenities...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Chavez House! C 1870: Spacious and Luxurious! Great Reviews!1 / 31
    (1)Excellent
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Grill
    • Satellite TV
    • Internet Access
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 April 2017
    This was my families first stay in Key West. The Chavez house was absolutely beautiful. All modern amenities and the location was close to everything! We didn't need our car...
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    About this property
    Newly available! The Historic Chavez House on Margaret Street! This 3 bedroom 2 bath two story eyebrow house was Built in 1870 and is in the National Register of Historic Places. Newly renovated and very well appointed! Fine linens, gorgeous furniture, ultra comfortable mattresses, and a cool...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    Eyebrow Suite-1 BR/1BA steps off Duval St.1 / 24
    (4)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Waterfront
    • Wi-Fi
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Hot Tub
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2017
    This was our 2nd time staying with Andrews Inn and Cottages. They are amazing!! The staff is very accommodating, the suites are wonderful, and we can't wait to go back. I highly...
    Reviewed 23 March 2017
    Eyebrow House has a ton of room, lovely front porch and rear patio. The negative for senior citizens is that it has only a queen bed and hideabed which works for kids, not...
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    About this property
    The Eyebrow House is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Poinciana House1 / 25
    (47)Excellent
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Grill
    • Satellite TV
    • Patio
    • Private Outdoor Pool (Heated)
    • Wi-Fi
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    The house was a 1/2 block off Duvall Street. Was close to all restaurants and attractions. The house was very cute and clean. The pool was fantastic. We would definitely stay...
    Reviewed 5 April 2017
    The Poinciana House is a wonderful small house with pool for two people. My wife and I stayed for a week and had a great experience. The house is perfectly located for...
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    About this property
    Poinciana House, a one-bedroom, two-full bath conch cottage, is a standout in authentic Florida design and guest friendliness. The private pool area and tropical garden is where you find the namesake Royal Poinciana tree complete with a chair hammock beckoning from one enormous branch. Swinging...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    La Prive1 / 25
    (22)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Shared Outdoor Pool (Unheated)
    • Patio
    • DVD Player
    • Wi-Fi
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    The four of us stayed at the residence for two weeks. We are all 68 plus. We were looking for a relaxing place to stay and found it. It is a ten minute walk from Duval Street...
    Reviewed 16 August 2016
    This is a very nice property in a quiet part of Old Town. We enjoyed the pool and chose the o cool in a couple of nights so it was easy. Great stay.
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    About this property
    This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting pool for the exclusive use of compound residents. La Prive has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Treetop Studio w/ Jacuzzi in Old Town, steps off Duval St.1 / 7
    (3)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • DVD Player
    • Washer
    • Hot Tub
    • Satellite TV
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 April 2017
    We booked the Treetop Studio for our first trip to Key West. Everything about it was perfect! The location is just a block off of Duval, but south of the crazy end, so the...
    Reviewed 29 March 2017
    What can I say? This was literally a perfect place from top to bottom. We stayed for a week and it was very nice to have a kitchen in room to save some $$. We loved going out to...
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    About this property
    The Treetop Studio is ideally located in a quiet three-unit compound a half block off Duval St. in the heart of Old Town Key West. Our guests enjoy the best of both worlds, as the restaurants, world-class galleries, and vibrant nightlife of Duval St. are just a few steps away. You feel like a local...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Air Conditioning
    • Washer
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Brand New! Solaris Cottage Garden, located on one of Key West most private slow lanes, and is a Bohemian Dream!. Perfect for a couple or single guest ready to explore all that Key West has to offer! This unique vacation rental just completed renovation December 1st 2016! All new furnishings and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Solaris Cottage: Historic Old Town Lane, 14 minute walk to Beach!1 / 24
    (5)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Internet Access
    • Grill
    • Air Conditioning
    • Washer
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 31 March 2017
    The cottage is located within 10 minutes of just about everything. Quiet street. The cottage was extremely well kept and clean. Kitchen was just what we needed-dishes, glasses...
    Reviewed 30 March 2017
    There's little you can't walk to from this quiet, private location. Beach, bars, restaurants - all right there!
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    About this property
    Solaris Cottage, located on one of Key West most private slow lanes, was built for you. We guarantee that the moment you step onto the front porch and into the cool, sun-dappled living area, your stress will drop away and your creativity will soar. This one-bedroom, one-bath unit is located on a...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Grande & Petite Maisons: Sleeps 12, Pool & Parking, Best Key West Location1 / 24
    (2)Excellent
    6 Bedrooms, 7 Bathrooms, Sleeps 12 Quick View
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    Amenities & Details
    • Internet Access
    • Air Conditioning
    • Balcony
    • Satellite TV
    • Grill
    • Washer
    • Private Outdoor Pool (Heated)
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    Recently a group of twelve close friends traveled to Key West for a few days of fun in the sun. Since we live in the Chicago area we wanted a place to stay that could house all...
    Reviewed 21 March 2017
    These two houses are a great place to stay. All new kitchen equipment, nice furnishings, all rooms have their own private bath plus a 1/2 bath on the first floor og the grande...
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    About this property
    Grand Maison and Petite Maison together sleep a total of 12 guests. They boast 6 bedrooms each with its own en suite bathroom. Spacious with plenty of room allowing for large family get-a-ways, reunions, or wedding parties. Great outdoor spaces where friends and family can gather or taking time...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 6 Bedrooms, 7 Bathrooms, Sleeps 12
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    4 Bedrooms, 5 Bathrooms, Sleeps 8 Quick View
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    • Private Outdoor Pool (Heated)
    • Internet Access
    • Air Conditioning
    • Grill
    • Satellite TV
    • Washer
    • Balcony
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Grand Maison on Duval is located in the Gallery District right on Duval Street near the Southernmost Point. The home is just a few blocks away from the Southernmost Beach, night clubs, and tourist areas which makes it a perfect spot to vacation as it is a quick safe walk to everything Key West has...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 5 Bathrooms, Sleeps 8
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    Pelican Landing Flamingo Retreat1 / 22
    (20)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Grill
    • Satellite TV
    • Terrace
    • Internet Access
    • Balcony
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 21 July 2013
    I chose the Pelican Landing due its proximity to Duvall Street and the ability to secure the rental for daily rates. The unit was spacious and had a lot of accommodations within...
    Reviewed 22 May 2013
    We stayed in a two bedroom unit, and had other friends in a separate unit. When we first pulled up we were a little worried because the outside is rather plain. We were...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Kali Zoi House - 28 Day Minimum1 / 27
    (1)Excellent
    3 Bedrooms, 3 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Grill
    • Washer
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Patio
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 4 weeks ago
    We had the best time staying at the Kali Zoi house! The location is absolutely perfect as everything seems to be walking distance. There were 5 of us in the house and there...
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    About this property
    28 DAY MINIMUM RENTAL TERM ONLY Kali Zoi is Greek for “good life.” That's what you'll have when you book a stay in this large, classic conch style house in historical Old Town. This 1,960 square foot, 2 story house has all of the charm of a 19th century home but was actually built in 1988 so it...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 3 Bathrooms, Sleeps 6
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    Quilted Giraffe1 / 25
    (2)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Patio
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Satellite TV
    • Wi-Fi
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 8 June 2011
    This cottage is perfect for a couple, with occasional visitors. Walking distance to everything, away from the Duval madness, and reflecting the owner's taste, this rental is...
    Reviewed 5 March 2010
    The heated pool and lush backyard foliage were the draw to this well appointed home. Parking was a nightmare, the neighbor to the right facing the house was most unpleasant. A...
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    About this property
    Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part of Old Town...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    Pelican Landing Harbor Island Retreat1 / 23
    (30)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Terrace
    • Shared Outdoor Pool (Unheated)
    • Grill
    • Internet Access
    • Satellite TV
    • Air Conditioning
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 March 2016
    When we arrived at Pelican Landing, we were greeted by one of the rudest workers I have ever dealt with in my life. I don't recall her name but if you can get past her and...
    Reviewed 15 October 2015
    Basically, it's just okay - not bad, not great. I felt like for the money we spent, it just should have been nicer. The whole place needed a new coat of paint. The carpet on the...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Pelican Landing Abaco Retreat1 / 48
    (12)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Internet Access
    • Terrace
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 April 2013
    Everything was as promised , great location , very nice and helpful staff .
    Reviewed 6 January 2013
    Very spacious with great balcony with dock/pool access. Would definitely stay again
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Tropical Escape1 / 26
    (84)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
    other travellers have booked this property
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    Amenities & Details
    • Air Conditioning
    • Hot Tub
    • Satellite TV
    • Patio
    • DVD Player
    • Washer
    • Wi-Fi
    • Private Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    This place is just perfect! Nice and clean, and check in was a breeze! But what I really loved about it is the location! You are in Key West, but you are far enough away from...
    Reviewed 2 weeks ago
    Owners were great and very accommodating. The condo is beautiful. Has everything you need. Pool was great to use. We would rent again when we come to key West. We had a great...
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    About this property
    This luxurious condo/hotel features a wonderful tropical interior design. It has 2 spacious bedrooms (one room with a king-size bed and a full bath and one queen-size bed with a full bath. The unit has a fully equipped kitchen that looks onto the living room with a queen-size sofa sleeper. The...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    A Touch of Bermuda in Key West1 / 19
    (16)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Satellite TV
    • DVD Player
    • Internet Access
    • Air Conditioning
    • Washer
    • Patio
    • Grill
    • Porch
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 1 week ago
    I stayed in Jack's condo (a touch of Cuba in Key West) this past week and we enjoyed every aspect of it. The condo is two bedroom one bath and was perfect for my party of three...
    Reviewed 20 September 2016
    My third trip to Key West this year. And question - WHY I did not stay here before??!!#@$ Great place, great location...two blocks of Duval, 100 feet to swimming pool and 5 min...
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    About this property
    NEWS BULLETIN. JUST HAD A BLOCK OF WEEKS OPEN UP FOR THE WEEKS OF AUGUST 19 TO OCTOBER 21 IN MY OTHER CONDO FIVE DOORS DOWN FROM MY COTTAGE THAT WILL ACCOMMODATE UP TO 4 PEOPLE SO I WILL DO RIGHT BY YOU WITH THE RATE IF THIS PROPERTY IS BOOKED. Now onto my vacation cottage.. Envision yourself...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    5 Bedrooms, 5 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Satellite TV
    • Wi-Fi
    • Private Outdoor Pool (Heated)
    • Washer
    • Hot Tub
    • Patio
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Whether you want to connect or reconnect with the island paradise of Key West, this residence, aptly named The Sanctuary, is a dream destination. Its L-shaped architectural design centers around a temperature-controlled pool, built-in hydro massage spa, graceful waterfall, and outdoor rain shower....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 5 Bedrooms, 5 Bathrooms, Sleeps 10
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    Pelican Landing Florida Retreat1 / 23
    (32)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Balcony
    • Satellite TV
    • Internet Access
    • Grill
    • Terrace
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 16 October 2015
    This condo was a bit dated and could a little TLC, but overall worked great. The location was nice on the water and was not too far from downtown. Everything worked really...
    Reviewed 4 September 2013
    Stayed at Pelican Landing in a group of 8. The interiors were all nice and comfortable with clean bathrooms and kitchen. Beds were comfortable and sheets were clean, sofabed was...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Pelican Landing St.John Penthouse1 / 20
    (32)Very good
    3 Bedrooms, 3 Bathrooms, Sleeps 10 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Balcony
    • Terrace
    • Grill
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 September 2013
    Relaxing fun time with friends. Rented beach cruisers and saw the island.
    Reviewed 19 July 2013
    Excellent friendly,clean, lots of linen and supplies. Rooms large and very cozy. loved the balconies and outside furniture. Everyone had smiles on their faces,it made you feel...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 3 Bedrooms, 3 Bathrooms, Sleeps 10
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    Pelican Landing Dominica Retreat1 / 21
    (25)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • DVD Player
    • Shared Outdoor Pool (Unheated)
    • Air Conditioning
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 10 March 2014
    Traveled with wife and brother and his wife. Very clean, nice size 1200 sf, convenient layout, Pool was nicely heated, adequate parking. about 3/4 of a mile from Malory Square...
    Reviewed 11 July 2013
    The condo was nice, a few updates are in order. More cooking untesils and cookware would be nice. Overall, clean, nice location, friendly neighbors and friendly and helpful...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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    Ann Street Gardens1 / 25
    (53)Very good
    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    Amenities & Details
    • Air Conditioning
    • Wi-Fi
    • DVD Player
    • Patio
    • Grill
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 weeks ago
    We absolutely loved the Ann Street cottage we rented. It was decorated very nice with stained concrete floor. The covered patio with grill was great. The pool I. The back was...
    Reviewed 15 August 2016
    I honestly hesitated to write this review because I want to keep it all to myself. My husband and I are unwilling transplants, having lived in Key West until about 6 years...
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    About this property
    (Ann Street Gardens is a 16+ compound. Regretfully, no children under 16 allowed.) The cottage is a cozy hideaway. The poolside area is picture-postcard perfect. The location is in the very heart of Key West's Old Town, a half a block off the world-famous Duval Street. In short, Ann Street Gardens...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    Pelican Landing Aruba Retreat1 / 21
    (38)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 8 Quick View
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    Amenities & Details
    • Internet Access
    • Balcony
    • DVD Player
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • Terrace
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 September 2016
    Even though the property may be older, they have done a great job up keeping the building and updating over the years so in turn this is a great apartment. A few blocks away...
    Reviewed 8 July 2014
    1960s property but well maintained with a good pool, new gas grills (all the better for cooking your catch) and located right on the marina. Our unit (1040) was on the first...
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    About this property
    Families are welcomed in our vacation rentals. Student groups are not permitted. Our minimum age requirement to rent is 25 years old. Everyone in your party must be 25 years old to check in unless accompanied by a parent. Our beautiful waterfront...
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    Location Information
    Key West, Florida Keys 33040
    Condo/Apartment - 2 Bedrooms, 2 Bathrooms, Sleeps 8
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