Florida Keys Vacation Rentals

(486 rentals)
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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautifully appointed 3rd floor ocean-view condo at the prestigious 1800 Atlantic Complex in Key West. This unit is an extra large floor plan with a nice ocean view. This property features 2 queen beds in the master bedroom and a king in the guest bedroom. Full size washer/ dryer and 1 assigned private ...

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Property Type

Key West Condo

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Big Coppitt Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Smathers Beach

$283

avg/night

$283
avg per night
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Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

3 bedroom 2 bath home, heated / chilled pool, plenty of parking for trailers / boats / on a deep water canal with a view to die for.

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Property Type

Big Coppitt Key House

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Key West Condo | On the beach
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$1540

avg/night

$1,540
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Mar Y Sol is a beautiful oceanfront condominium featuring three bedrooms and two and a half baths, located at 1800 Atlantic. Enjoy the balmy breezes from your 60-foot private wrap-around balcony, offering a stunning view of the Atlantic Ocean.Mar Y Sol includes renovated kitchens and bathrooms.The ...

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Property Type

Key West Condo

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Summerland Key House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$349

avg/night

$349
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for the perfect getaway for your Florida Keys Vacation? Look no further! Tropical Oasis is just the home for you and your guests with only 23 miles to Key West!This two bedroom and two bath home, located on Summerland Key, is situated on a corner canal allowing easy access to open water for ...

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Property Type

Summerland Key House

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Key West Condo
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
1 review

Distance to beach: 0.5 miles to Ft. Zachary Taylor State Park

$397

avg/night

$397
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

So welcome to Key West and the Shipyard section of the Truman Annex. You have many choices of accommodations and since I am not a real estate salesman or property manager, allow me let the photos and description speak for themselves. My over sized two bedroom, one bathroom condominium end unit (cross ...

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Property Type

Key West Condo

Featured review

"A touch is all you need…"

A touch of Cuba was the perfect little spot. We are now spoiled to the conveniences of renting direct with the owner, having Class A rated efficiencies, Beach, Bikes, Pool, very quiet and well kept area ...

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

The k2 escape is the very best in indoor/ outdoor living. The full size heated pool is surrounded by lush mature tropical landscaping with your very own backyard poolside sandy beach. Tiki hut bar, outside cabana living room, zen outdoor shower and sun deck enhance this Centrally located Key West retreat. ...

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Property Type

Key West House

Featured review

"Highly Recommend!"

My husband and I recently rented this home for a month and we couldn’t have enjoyed it more! Let me start with our favorite space… the backyard. From the heated pool, to the outdoor shower, guest house, ...

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Marathon House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Completely remodeled 3 bedrooms, 2 bath house in Marathon - the middle of the Florida Keys, on Mile Marker 51, only one hour to Key West. OUR WEEKS ARE SATURDAY - SATURDAY. Beautiful place in a quiet neighborhood. Direct access to the ocean, with 37 feet of dock. House set up for fishing and relaxing. ...

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Property Type

Marathon House

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Marathon House
5 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4 bathrooms
1 review

Distance to beach: 3 miles to Sombrero Beach

$484

avg/night

$484
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Come and live the KeyZ life for the week or the month! Gorgeous home just off the open water on a deep water canal gulfside. This is a boater/fishing paradise with 60 feet of docking space, deluxe fish cleaning station located on the gulfside! Relax poolside at our signature swimming pool/tiki gar ...

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Property Type

Marathon House

Featured review

"Wonderful Rental"

We came with our family of 10 and had a wonderful time. The house was perfect for us. It is beautiful and spacious. The outdoor area is fantastic with a sun deck, two sofas and large sun umbrella. The ...

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Cudjoe Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

$159

avg/night

$159
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This Cudjoe Key home is neat as a pin with all the comforts of home. Bright and shiny kitchen with everything you may need to create wonderful get together. The large comfortable living room has plenty of seating including recliners in the sofa and loveseat. Laminate hardwood floors throughout. 3 large ...

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Property Type

Cudjoe Key House

Featured review

"Wonderful relaxing vacation home"

We recently stayed at the Sunset Bay home and couldn’t have been happier with the rental. Never having rented a home in the Keys I wasn’t sure what to expect but the Action Keys realty team was efficient ...

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Islamorada House
2 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 2 bathrooms
2 reviews

$118

avg/night

$118
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Located at Mile Maker 87 Bayside. This gated condo complex offers a large heated pool, club house, Jacuzzi, two tennis court, large Bayside beach. This townhouse (sleeps 8) has just been totally renovated with beautiful tropical furniture, all new kitchen, small garden patio with hammock, living room ...

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Property Type

Islamorada House

Featured review

"Great vacation"

We have never stayed in the Florida Keys before so this was a new adventure that we will definitely do again. The weather was a perfect 80 degrees. Nothing but chill time. We would start the day in the ...

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Big Pine Key House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$137

avg/night

$137
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Simple and sweet with no muss, no fuss. It’s all right here – Gulf Side! This quaint two bedroom vacation home offers views, a deep-water boating and swimming canal and a protective seawall. This home offers 2 queen-size beds and an additional sleeper sofa.A glassed-in porch and all the ...

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Property Type

Big Pine Key House

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$450

avg/night

$450
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautifully renovated 2 bedroom 2 bath ocean view condo at 1800 Atlantic available for monthly rentals. King in the master, queen in the second bedroom and a double pull out in the living room. The unit is tiled throughout. The bathrooms have been nicely upgraded and did we mention the view from Poolside ...

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Property Type

Key West Condo

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Islamorada House
3 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3.5 bathrooms
2 reviews

$978

avg/night

$978
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the coastal home of your dreams in the relaxed residential retreat of Coral Cove. As soon as you pull into our driveway, you’ll be able to walk, bike or paddle everywhere in town. Our newly constructed two-story house has 3 spacious bedrooms, a study area with bunk beds, plus 3 and ...

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Property Type

Islamorada House

Featured review

"Bayside Paradise Perfection"

Our family has been traveling to Islamorada for Spring Break for the last 4 years and this was by far our favorite place to stay! Our family enjoyed the private oasis that the townhome provided. We felt ...

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Key West Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$989

avg/night

$989
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pool
  • WiFi

About this property

This condo has been beautifully renovated. Both bedrooms and the living room open onto a spacious 40 ft private balcony. There is a King Bed in the Master bedroom and 2 twin beds in the guest bedroom.1800 Atlantic is directly on the Atlantic ocean in Key West, adjacent to Smathers Beach the City ...

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Property Type

Key West Condo

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Key Largo House
5 BR | 5 BA | Sleeps 15 | Quick View
Sleeps 15, 5 bedrooms, 5 bathrooms

$569

avg/night

$569
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This is a large 5 bed / 5 bath single family home which is located on a very quiet residential deep waterfront canal in oceanside Key Largo. There are no bridges to the ocean and within minutes of your 70’ sea wall dock, you will be in the open waters of the Atlantic and the John Pennekamp State ...

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Property Type

Key Largo House

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Little Torch Key House
3 BR | 2.5 BA | Sleeps 7 | Quick View
Sleeps 7, 3 bedrooms, 2.5 bathrooms

Distance to beach: 5 miles to Bahia Honda

$297

avg/night

$297
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to "SUNSET LANDING". Located in one of the best boating areas in the Florida Keys, this beautiful 3 bedroom, 2 1/2 bath home overlooks the salt ponds facing west for your own private sunset viewing every night. It is tastefully decorated with all the amenities you need to enjoy your ...

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Property Type

Little Torch Key House

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Summerland Key House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$313

avg/night

$313
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to the cleanest blue water flow-thru canal in the Keys! This comfortable home is clean and conveniently located at MM 24.5 on Summerland Key, near the beginning of a deep blue water canal.This elevated CBS home has concrete floors covered in ceramic tile and carpet in the bedrooms. The ...

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Property Type

Summerland Key House

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Marathon House
4 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 4 bathrooms
1 review

$1161

avg/night

$1,161
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Must See Stunning 3095 Sq. Ft 4/4 SFH on ground level with pool, 45 ft of dockage, outdoor kitchen and access to the ocean by boat.This gorgeous property features an open floor plan with elegant furnishings, state of the art kitchen with Viking appliances and an induction cooktop, quartz countertops, ...

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Property Type

Marathon House

Featured review

"Sunny Daze in Marathon!"

I didn’t know much about Marathon other than it was in the keys. Upon hearing from a family friend that it was the Keys best kept secret we couldn’t resist. The Sunny Daze house was perfect for my family ...

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Big Pine Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$213

avg/night

$213
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Barracuda Bungalow in Big Pine Key! This quaint ground level home is perfect for your next Florida Keys getaway. There's plenty of space with 3 bedrooms and 2 baths, it's pet friendly, has a brand new pool and hot tub and sits on a great boating canal! Bring the whole family and the ...

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Property Type

Big Pine Key House

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Key West Yacht
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom
2 reviews

$244

avg/night

$244
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

We specialize in amazing vacations and honeymoon and extended stays for two guests, aboard a yacht that stays dockside without the chance of seasickness allowing you to come and go according to your own schedule. Our pedigree Hatteras, a custom 60' motor yacht, a timeless classic designed for elegant ...

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Property Type

Key West Yacht

Featured review

"Great experience!"

The Paradise is a grogerous yacht. The woodworking is amazingly beautiful. The bed is very comfortable. We really enjoyed our stay and was very pleased. Captain Berry & Tamara were very tentative and superior ...

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Cudjoe Key Villa
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$393

avg/night

$393
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a home away from home? Via Villa is the place! This vacation home is located in Cudjoe Gardens on Cudjoe Key, only 20 miles from Key West. Situated on a corner canal, there is ample dockage for large boats, water and electric on the dock, as well as a waterside fish cleaning table. Via Villa ...

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Property Type

Cudjoe Key Villa

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Key West House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • WiFi

About this property

3-Bedroom, 1.5-Bath Historic Conch House in the Heart of Old Town Key WestThis charming Conch house features a queen bed in the master bedroom, a queen bed in the first guest bedroom, and two queen beds in the second guest bedroom. The kitchen has been beautifully renovated, and there is a wonderful ...

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Property Type

Key West House

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Islamorada House | On the beach
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$1377

avg/night

$1,377
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Nestled between the Cheeca Lodge and Caribbean Resort, our 4-bedroom oceanside home offers a unique beachfront experience for those looking for a luxurious and private getaway. Each spacious bedroom and en suite bathroom is inspired by modern coastal furnishings. Perfect for entertaining family and friends, ...

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Property Type

Islamorada House

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Summerland Key House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
3 reviews

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Keys Life Come on down to “Keys Life” and enjoy a great Florida Keys vacation. Located in one of the best deep-water boating areas. The crystal blue canals and superb deep-water boating will make your fishing days a dream. Great outside entertaining areas with a perfect pool to splash around ...

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Property Type

Summerland Key House

Featured review

"Keys life"

Enjoyed our stay at Keys Life. The home was beautiful. The weather was quite windy so we weren’t able to get out as much as we wanted in our boat but we were able to get some nice lobster! It was nice ...

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Marathon House
2 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 3 bathrooms
14 reviews

Distance to beach: 1 miles to Sombrerro Beach

$452

avg/night

$452
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Lemon Key CottageWelcome home…Thanks to Hurricane Irma, we now have a beautiful newly renovated home! We've spent over $150K on a complete restoration and modernization. (check out the new pics) Lemon Key Cottage is absolutely stunning with new: bathrooms, kitchen, appliances, flooring, ...

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Property Type

Marathon House

Featured review

"Christmas Vacay"

10 ️ Rating! I called Florida Rentals. I Booked. Counted Down the days until our Christmas vacation began. We were able to take homemade cookies to the USCG base on Christmas Day. We were able to see ...

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Summerland Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$179

avg/night

$179
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Florida Keys Vacation Rentals – This Summerland Key vacation home is situated on a private, fully fenced lot, with a tastefully decorated interior with great features such as hardwood floors and a beautifully well-equipped, custom kitchen. Spacious living and dining rooms provide ideal entertaining ...

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Property Type

Summerland Key House

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Key West House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
2 reviews

Distance to beach: 2 miles to Smarthers Beach and Higgs Beach

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Rate reduced for December 2024. This home sits in Key Lime Grove Subdivision which I was born and raised in. It is a neighborhood rich in history and conveniently located on the Island. This home welcomes you with a white picket fence! It has been nicely upgraded down to the wood floors and crown molding ...

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Property Type

Key West House

Featured review

"Great getaway"

This house has everything we need. The best part is the private backyard with lovely gardens and a pool and an outdoor shower. Inside is also wonderful with 3 bedrooms, a big kitchen, a dedicated office, ...

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Little Torch Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Cape Cod South! This comfortable home is located 4 lots from the open water on the Gulf side of Ramrod Key. It sleeps 6, has a beautiful clean lot with a concrete dock, and sneak peak views of the open water. There is plenty of storage downstairs for your gear along with an extra bait freezer ...

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Property Type

Little Torch Key House

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Key West Apartment
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

$222

avg/night

$222
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

Galveston Porches Stylish one bedroom apartment in the heart of Old Town. Totally renovated and beautifully decorated. Everything you will need for your perfect Key West extended stay. 1 assigned parking space with the apartment. Full kitchen and washer dryer, Central AC and wifi access. The owners have ...

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Property Type

Key West Apartment

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Sugarloaf Key House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$229

avg/night

$229
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

This bright, very spacious and inviting, nicely-maintained Sugarloaf Key home is located just 20 minutes north of Key West. Nestled back in a beautifully manicured neighborhood and not far from Sugarloaf Lodge and Marina, you will have nearby access to boating, fishing, kayaking and a few local restaurants.An ...

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Property Type

Sugarloaf Key House

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Tavernier Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$250

avg/night

$250
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Within a 10 minute drive of Key Largo or Downtown Islamorada's best Restaurants, Bars, State Parks, Dive Boats & Fishing Charters.You'll enjoy this Charming 2 bedroom 2 bath suite with sleeper sofa in Ocean Pointe Suites; a private gated community nestled on the Atlantic's Edge.Located ...

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Property Type

Tavernier Condo

Featured review

"Perfect vacation"

We enjoyed staying at this property. The owners communicated quickly and provided good information and recommendations. The condo is clean and the perfect amount of space for our family. The location was ...

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Islamorada Townhome
2 BR | 1.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

We are delighted to offer this 2 story, 2 bedroom, 1 1/2 bathrooms OCEANFRONT TOWNHOUSE!!! There are a limited number of oceanfront townhomes available at Planation By The Sea! Enjoy the breathtaking views off of all 3 balconies catching the sunrise and sunset. The main living area and upstairs bedroom ...

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Property Type

Islamorada Townhome

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Key West Cottage
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Escape to the laid-back charm of Key West with The Gumbo Limbo Cottage, a beautiful and beachy vacation rental. Nestled in the heart of the island, this charming 1933 shotgun house has been impeccably restored and uniquely decorated, creating a tranquil and inviting atmosphere for your month-long getaway.As ...

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Property Type

Key West Cottage

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Key West Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Hot tub
  • Pool
  • WiFi

About this property

Beautifully renovated 2 bedroom 2 bath condo at the exclusive 1800 Atlantic Condo's. Each bedroom has a king size bed and plenty of closet space. Both have access to the private balcony that faces the nature preserve in a quiet tranquil location at the property. The unit is located across from the ...

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Property Type

Key West Condo

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Marathon House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$732

avg/night

$732
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Welcome to Tropical Sunsets, your tropical oasis in the heart of Marathon, Florida! This stunning 4-bedroom, 3-bathroom home offers a serene escape with breathtaking Gulf views, luxurious amenities, and a perfect location for relaxation and adventure.Property Overview:Prime Location: Tropical ...

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Property Type

Marathon House

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Key Largo Apartment | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

Inquire for rates

Inquire for rates

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Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Remodeled in 2023 - 2 Bedrooms & 2 Full Baths, Washer & Dryer in Unit, new Smart Appliances, 75 Inch TV, Computer Desk & Monitor, Fastest WIFI Speed Available! w/ all Cable Channels , Master has a King Bed, Guest has a Queen Bed and a Twin Bed, Entry with Key and/or Code, Open Concept w/Glass ...

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Property Type

Key Largo Apartment

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Florida Keys Vacation Rentals