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Florida Keys Cottages

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    Travellers to Florida Keys are booking December dates now. Secure your vacation rental today, and have the perfect trip.
    38 Matching Rentals in Florida KeysView all 1,347 rentals
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    Bayfront Cottage, Beach, Dock, Marina1 / 56
    (3)Very good
    1 Bedroom, 1 Bathroom, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Casa Manana Conch Cottage1 / 41
    (8)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • DVD Player
    • Satellite TV
    • Patio
    • Grill
    • Internet Access
    • Air Conditioning
    • Private Outdoor Pool (Unheated)
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 23 April 2012
    We've stayed in 4 different vacation rentals for a month or more at a time, and I think we enjoyed Casa Manana the best. Lots of character, great location, friendly cats and...
    Reviewed 2 July 2011
    The home was wonderful & the perfect size for our family. It was close to everything & we enjoyed the nearby church bells while sitting by the pool. We were surprised...
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    About this property
    Casa Mañana at 800 Virginia Street is perfectly situated for the guest who wants to enjoy Key West at its finest. Located just three blocks from Duval Street, home of world famous watering holes, shopping, and dining, this Old Town jewel is just steps away from Fausto’s Food Palace, Sandy’s Café,...
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    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Waterfront Key Largo Bayside Cottage Paradise1 / 20
    (28)Excellent
    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
    Kid friendly
    Smoking allowed
    Reviewed 21 May 2017
    Just a great place to hang your hat and kick back. Water front tranquility. Like having an aquarium and tropical ecosystem as your back yard, lizards included, then this is...
    Reviewed 13 May 2017
    Beautiful location and it felt like we were home. Gladys even provided beach towels (which we forgot) and throw blankets for watching TV. Every little detail was taken care of...
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    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...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 4 Bathrooms, Sleeps 4
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    Atlantis House Master Suite1 / 22
    (21)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Housekeeping Included
    • Air Conditioning
    • Patio
    • Hot Tub
    • Parking
    • Wi-Fi
    • Satellite TV
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 17 December 2015
    My husband and I stayed with Kayla and Steve for five days and it was the most relaxing fun filled stay ever. The accommodations were very clean and our hosts were the...
    Reviewed 12 February 2015
    Atlantis House is a very special hideaway. It is called a guest house, and we were truly the guests of Steve and Kayla. They were so welcoming from the day we arrived...
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    About this property
    About Us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique Guesthouse with only 2 suites... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both...
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    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Tropical Cottage with Sandy Beach1 / 12
    (46)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Washer
    • Waterfront
    • Grill
    • Satellite TV
    • Balcony
    • Internet Access
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 August 2017
    We stayed in the pet friendly cottage. It was my husband and I, my 2 college age kids, and our 2 yorkies. Very comfortable 2 bedroom, 2 bath cottage nicely decorated and...
    Reviewed 13 July 2017
    Absolutely the best place to stay in Key Largo! My family and I stayed and fell in love. It's very comfortable, stocked very well and the property and views are amazing! We will...
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    About this property
    Cozy cottage with sandy beach located in Key Largo on an acre of tropical waterfront. The children will enjoy playing on the beach with toys provided. Or fish from the 100ft dock with fishing equipment provided. Bring a boat and have FREE dockage. Lounge in the hammock under the palm trees and...
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    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Florida Keys Sailing on Conch Key. Bayfront 2 BR cottage with 23 foot Sailboat1 / 19
    (14)Excellent
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Waterfront
    • Wi-Fi
    • Porch
    • Satellite TV
    • Ocean Views
    • DVD Player
    • Air Conditioning
    • Grill
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 11 September 2017
    We LOVED Conched Out! The cottage was stocked with everything! The cottage is what we expected to see in the Keys. It was like we stepped back in history and got to admire this...
    Reviewed 4 August 2017
    My wife and I along with another couple spent a wonderful week on Conch KeyOur house had a full kitchen. dining room, living room and two bedrooms. Our back door was just ten...
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    About this property
    Our Florida Keys tradional island home is a fully furnished 2 bedroom, 1 bath plus Florida room with a deck overlooking the bay. It is surrounded by lush vegetation and large towering coconut palm trees. The house has been decorated in a nautical flavor with many fine antiques collected from around...
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    Conch Key, Florida Keys 33050
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    Two Bedroom Historic Hideaway Olivia Retrea Private Pool  Key West- Monthly1 / 26
    (1)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Private Outdoor Pool (Unheated)
    • Satellite TV
    • Grill
    • DVD Player
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 August 2015
    This is a lovely home that is obviously well loved by the owners. Everything is well maintained the pool is sparkling clean. There is beautiful artwork throughout the home. It...
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    About this property
    Look no further you have found a beautiful 2 bedroom 2 bath 'Shot-Gun' house in the heart of Old Town Key West, just 4 blocks from Famous Duval Street. This great property is very spacious and will accommodate up to 6 guests comfortably. There is a Fully equipped kitchen with a full size dining...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    Conch Key TreeTop one BR Cottage with 23' Sailboat1 / 23
    (18)Excellent
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • DVD Player
    • Waterfront
    • Grill
    • Air Conditioning
    • Wi-Fi
    • Balcony
    • Satellite TV
    • Ocean Views
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 August 2017
    Sailing,kayaking,fishing,riding bikes across 2 1/2 mile bridge if you are into that . Beautiful sun sets to see night time offers hearing the palm trees while the ocean breeze...
    Reviewed 5 July 2017
    Great sailboat and other amenities. Barry and Tammy are wonderful. Easy to be very active or very lazy at this rental. Sail, bbq, watch sunset in kayak, take chairs and sun...
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    About this property
    This one bedroom, one bath cottage is located high in the swaying coconut trees overlooking the water. The living room area has sliding glass doors that open onto a small deck area with a water view. The bedroom is tastefully furnished with an antique queen bedroom set and the entire cottage is...
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    Location Information
    Conch Key, Florida Keys 33050
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    Quaint KeyLargoCottage, 1 bedroom,sleeps 4 comfy1 / 40
    (25)Very good
    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
    • Grill
    • Porch
    • Parking
    • Air Conditioning
    • Satellite TV
    • Washer
    • Outdoor Dining Area
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 18 July 2017
    This cottage is just as advertised. Just spent 4th of July week here and our stay was perfect. This cottage is conveniently located to Islamorada and Marathon we traveled all...
    Reviewed 11 December 2016
    We stayed 5 days/4 nights in early December. Two adults and a 40lb dog, plenty of room and the place had everything we could possibly need: tidy bathroom with full-size...
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    About this property
    Quaint cottage located on mile marker 100. Key Largo is known as the 'Dive Capital of the World.' John Pennekamp Coral Reef State Park has two beaches, and a replica of a shipwreck in the water which is great for snorkeling. We are located only a few blocks from the Marina where you can go fishing,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 3 Quick View
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    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Hideout Cottage has a full size bed and one single bed, kitchenette with 4 burner electric stove, full-size microwave, small fridge with complete kitchen and dining utensils plus linens and towels are provided. This cottage can sleep 2 adults with 1 child or 2 children if a provided cot is...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 3
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Patio
    • Ocean Views
    • Waterfront
    • Grill
    • Hot Tub
    • Washer
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Hidden Hammock Resort is located in Summerland Key, the Florida Keys' best kept secret! Our premium location just 23 miles from Key West allows you to enjoy the festivities and nightlife of Duval Street while still having a nice and quiet retreat to come back to. When you're ready to relax, we'll...
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    Location Information
    Summerland Key, Lower Keys 33042
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Patio
    • Housekeeping Included
    • Wi-Fi
    • Private Garden
    • Air Conditioning
    • Parking
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    About us... #1 rated Guesthouse in Key West on TripAdvisor for 2016 and 2017! Romantic, Private, Boutique.... steps away from the Beach and Ocean and the Key West Marine Park. Free bike use, super fast WI-Fi and off street parking! Reserve 1 room for a couple or both rooms to accommodate up to 4....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Waterfront Cottage with boat1 / 10
    (2)Average
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Wi-Fi
    • Washer
    • Grill
    • DVD Player
    • Waterfront
    • Air Conditioning
    • Satellite TV
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2015
    Wonderful location for paddle boarding. Saw manatees every day. Not to far from shopping, restaurants and local businesses for boat rentals or snorkeling. The house has clean...
    Reviewed 30 December 2014
    We rented this property for a family Christmas vacation. We had a great time.Pros:Lots of screened in outdoor space including a dining set.Plenty of parkingDock and...
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    About this property
    Keysey home with direct access to the bay or ocean from the dock. Centrally located to stores, restaurants and all that Key Largo has to offer. We are located 2 miles from Pennekamp Park and 4 miles from the Jacobs Aquatic Center. Enjoy the Manatees swimming at the dock or fish and snorkel at the...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Grill
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Internet Access
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Beautiful Sailfish Cottage is right in front of the bay and has it's own tiki hut facing the water with my personal favorite, a tiki shower for 2 containing 4 relaxing shower heads. It's a freestanding cottage which sleeps 2. We also call this cottage the Honeymoon Suite. Please call/email for...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 5 Quick View
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    • Air Conditioning
    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The elevated queen-sized bed in the Keys Cottage is surrounded by a unique wall mural and has a super-comfy memory foam mattress. Decorated with a Spanish pirate influence, the cottage also features a kitchenette with small fridge, stovetop, toaster, coffee machine and complete kitchen and dining...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 5
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    Ann Street Tranquility:  A cozy and peaceful cottage1 / 16
    (49)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Amenities & Details
    • Satellite TV
    • Grill
    • Air Conditioning
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 October 2016
    Returning to Ann Street. Such a comfortable bed!!We love the little Ann Street compound with its secluded pool and lush gardens. Tranquility was the perfect size for us two...
    Reviewed 19 September 2013
    Owners were unbelievably nice from the beginning of communication with them! This cottage lives up to its name. I'm pretty sure the maid skips the bathroom when she cleans in...
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    About this property
    This charming one bedroom cottage is the perfect hideaway. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer. Within 2 blocks you'll find Key West classics like The Bull, Sloppy...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Southernmost Retreat- 1 Block from Duval1 / 99
    (4)Very good
    3 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    • Patio
    • Grill
    • Porch
    • Air Conditioning
    • Outdoor Dining Area
    • Internet Access
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 3 January 2017
    This is a nice spot right of strip. Place is more for a family w young kids. Third bedroom is kinda small. Other than that place was real confronting. Enjoyed how close to...
    Reviewed 9 November 2015
    Enjoyed our stay here. Fairly sparse furnishings, but clean and functional. Location and price were the best points for this cottage. Short walk to everything, location is just...
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    About this property
    Just 1 short block from Duval Street the Southernmost Retreat is a recently renovated and decorated 3 bedroom, 2 bath house located Simonton Street. The Southernmost Retreat is located in the Simonton Historic Cottages enclave and is surrounded by fine restaurants, art galleries, shopping and in...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 3 Bedrooms, 2 Bathrooms, Sleeps 6
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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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    • 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 3 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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    Key West, Florida Keys 33040
    Holiday Rental House - 4 Bedrooms, 3 Bathrooms, Sleeps 7
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Mermaid Cottage is located between the Jungle Cottage and the Manatee at the aft of the property. It has been nicely painted with coral reef and mermaid setting by a well-known Canadian artist. It has a queen size bed, 1 bunk bed which can sleep 2 kids, kitchen and dining utensils, microwave,...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Wi-Fi
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Dolphin Cottage is a nice freestanding cottage located aft of the Captain’s Unit. Although this unit does not face the water it is only about 100 feet to the beach, waterfront tiki hut, sailboats and water toys. It has beautiful screened in patio and can sleep 2 adults and 2 kids. It has a...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Air Conditioning
    • Wi-Fi
    • Parking
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Jungle Cottage is originally part of the fishing camp back in the 50s which has now been decorated and custom painted by a local artist who shares the same name as the popular sailboat (The Morgan). Our Jungle Cottage has a king size bed, 1 bunk bed accommodation for 2 kids in a separate room...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • 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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    Tranquility1 / 24
    (29)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 4 Quick View
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    • Terrace
    • Wi-Fi
    • Satellite TV
    • Grill
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Balcony
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 14 June 2017
    Tranquility is a true Key West experience...clean cottage, clean pool, great location! Plan to rent bikes as parking is VERY limited and once you park your car you will not...
    Reviewed 28 June 2015
    The Tranquility Cottage (#5 at The Colony Cottages) is adorable. The cottage is bright, cutely decorated, and the compound is quite inviting. It is conveniently located and an...
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    About this property
    TRANQUILITY - The epitome of life in Key West, this charming cottage is full of color and creativity, lovingly restored with no detail overlooked for a Key West vacation rental Florida. Fabulous artwork, fun collectibles, beautiful stained glass all give this cottage the unique feel that keeps...
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    Location Information
    Key West, Florida Keys 33045
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 4
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    2 Bedrooms, 2 Bathrooms, Sleeps 5 Quick View
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    • Patio
    • Satellite TV
    • Wi-Fi
    • Balcony
    • DVD Player
    • Washer
    • Air Conditioning
    • Parking
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Open floor plan 2/2 kitchen, living and dining step right out to deck overlooking canal with a direct view to the bay 60 ft dock master bedroom has a king size bed and guest room has 2 twin beds. Great boating facilities you can dock behind the property and be in the Florida Bay in no time at all...
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    Location Information
    Tavernier, Key Largo 33070
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 5
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    • Grill
    • Waterfront
    • Satellite TV
    • Air Conditioning
    • Parking
    • Wi-Fi
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Captain's Unit can sleep 2 adults and 1 to 2 kids. It is a one-bedroom suite with its own Jacuzzi tub and a tiki shower. It has 1 king size bed, which also faces the water. An additional bedroom with 2 single beds (bunk bed style)which can be opened for this cottage making it a 2 bedroom. This...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    FREE Kayaks, Fishing, Sail, Snorkel W/ Cottage!1 / 46
    (1)Very good
    2 Bedrooms, 1 Bathroom, Sleeps 6 Quick View
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    • Parking
    • Waterfront
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    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Owner’s Cottage is also right in front of the bay with 2 bedrooms; it can sleep 2 adults and 1 to 3 kids. The main bedroom has a queen size bed; the second bedroom has a queen size loft bed and a twin bed on the ground floor. There’s also a full size pullout sofa bed in the living room. The...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 6
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    ROBERT FROST COTTAGE1 / 10
    (1)Very good
    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    • Wi-Fi
    • Air Conditioning
    • Satellite TV
    • Private Garden
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 19 November 2016
    This place was very nice and cozy just steps away from duval . Perfect for a quiet get away for you and/or your spouse . I've stayed many places and this one was just right for...
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    About this property
    Over 100 miles from mainland Florida and the southernmost point in the United States, Key West has attracted numerous artists and writers, including Ernest Hemingway, Wallace Stevens, Ralph Ellison, Elizabeth Bishop, Tennessee Williams, Robert Frost, and James Merrill. At 410 Caroline Street is...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Internet Access
    • Patio
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
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    Ann Street Cottage: A bright and airy home near Duval Street1 / 24
    (47)Very good
    1 Bedroom, 2 Bathrooms, Sleeps 2 Quick View
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    Amenities & Details
    • Patio
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • Internet Access
    • Air Conditioning
    • DVD Player
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 2 July 2013
    I selected this cottage via computer. The location is excellent for seeing ALL the sights of Key West. This cottage is as represented. The kitchen was spacious and nicely...
    Reviewed 1 August 2012
    The location is excellently placed in Key West. My girlfriend and I were never more than a 15 minute walk to anything that we needed and the kitchen had many of the things we...
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    About this property
    Tucked away in an inviting compound you'll find the perfect hideaway called Ann Street Cottage; a charming one bedroom cottage. The quiet compound is located just one block from Duval Street combining the best of both worlds for relaxing and taking advantage of all that Key West has to offer....
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 2 Bathrooms, Sleeps 2
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Satellite TV
    • Internet Access
    • Grill
    • Private Outdoor Pool (Heated)
    • Air Conditioning
    • DVD Player
    • Patio
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    This newly renovated unit is located just two blocks from world famous Duval Street surrounded by coconut palms and blooming bougainvilleas this charming one bedroom bungalow is a true island hideaway. The bungalow features an one level open space living/dining area, full kitchen and a spacious...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 2 Quick View
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    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    The Manatee Cottage is originally part of the fishing camp triplex back in the 50s which has now been newly tropically decorated by the owner with emphasis on manatee and sea life. It has a partial view of the bay. This cottage has a king size bed, 1 bunk bed accommodation for two kids in a...
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    Location Information
    Key Largo, Florida Keys 33037
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 2
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    Ann Street Gardens1 / 25
    (56)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
    My husband and I have stayed in several places in Old Town KW. This little spot is a hidden gem. It is quirky KW at its finest! Perfect location for a couple just wanting to...
    Reviewed 11 August 2017
    This place exceeds all expectations! Location is perfect, staff is amazing we will book Year after Year! Thank you Tim, Bill and Sabrina! The Desjarlais family
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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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    Key West Ginger Whole House1 / 23
    (50)Very good
    2 Bedrooms, 2 Bathrooms, Sleeps 6 Quick View
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    Amenities & Details
    • Parking
    • Wi-Fi
    • Grill
    • Satellite TV
    • Hot Tub
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 12 July 2016
    I just stayed at the Key West Ginger House with my husband and family and my big dog and it was great. The location is the best since it is on the Southernmost Point, close to...
    Reviewed 16 October 2014
    We enjoyed our stay at Ginger House (just 2 of us for 25th wedding anniv.) . So clean and comfortable. Great private patio out back. Jewel of a view of sun and moon and stars...
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    About this property
    KEY WEST GINGER HOUSE - An absolute jewel of a Key West vacation home a few doors from Duval Street, named for the breathtaking ginger plants blooming in our tropical paradise. Key West Ginger House is a historic home built in 1933, the epitome of what you have in mind when you are thinking about...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 6
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    CHARMING KCB POOL COTTAGE, PVT POOL,46 FT DCK,WIFI1 / 57
    (21)Excellent
    2 Bedrooms, 2 Bathrooms, Sleeps 4 Quick View
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    Amenities & Details
    • Wi-Fi
    • Satellite TV
    • Washer
    • Air Conditioning
    • Patio
    • DVD Player
    • Private Outdoor Pool (Heated)
    • Waterfront
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 7 August 2017
    Stayed for a week at Michelle's lovely beach cottage with my husband and 2 sons. The layout of the place is great--even though it is small it is well thought out and everyone...
    Reviewed 10 July 2017
    My family and I had a wonderful vacation staying at this well equipped house! Michelle, the Owner, had everything you could ever need while staying at the Keys! We also...
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    About this property
    $1,500 (Standard Rate for 2017) - additional rates apply to holidays and Lobster Weeks.ASK ABOUT REDUCED FALL RATES! (September 2017- December 22, 2017) Reduced rates do not apply to holiday weeks. PRIVATE-ON-SITE POOL, 45 FT DOCK, PRIVATE BEACH ACCESS AT EXCLUSIVE INCH BEACH- TAGS INCLUDED,...
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    Location Information
    Key Colony Beach, Florida Keys 33051
    Holiday Rental House - 2 Bedrooms, 2 Bathrooms, Sleeps 4
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    1 Bedroom, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Air Conditioning
    • Parking
    • Private Garden
    • Wi-Fi
    • Satellite TV
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    About this property
    Key West Cottage located in Mid-town away from the maddening crowd when you want to be and close enough to join in when you're ready. <BR><BR>Our cottage is surrounded by lush vegetation including: coconuts trees, mango trees, tamarind trees, banana plants, guava plants, Spanish lime trees and...
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    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 1 Bedroom, 1 Bathroom, Sleeps 4
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    2 Bedrooms, 1 Bathroom, Sleeps 4 Quick View
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    Amenities & Details
    • Internet Access
    • Satellite TV
    • Shared Outdoor Pool (Unheated)
    • DVD Player
    • Patio
    • Air Conditioning
    Suitability
    Pet friendly
    Kid friendly
    Smoking allowed
    Reviewed 13 October 2014
    Nice place. Quiet location. I would have thought someone might clean the pool during our stay since the iguanas in the trees used it for their bathroom quite frequently...
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    About this property
    This property has it all! The styling of the original shot gun homes of Key West restored with a beautiful natural cypress exterior combines with the clean lines of a contemporary home. Each Twin opens to it's own semi-private deck and lounge area with steps into a large kidney shaped pool with...
    View all property information
    Location Information
    Key West, Florida Keys 33040
    Holiday Rental House - 2 Bedrooms, 1 Bathroom, Sleeps 4
    Make Enquiry
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