Florida Keys Vacation Rentals

(486 rentals)
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Cudjoe Key House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$281

avg/night

$281
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This home is situated on a beautiful canal in the prestigious Cudjoe Gardens. It is impressive from the moment you pull in the driveway! There is a tropical grand entryway leading into the spacious and beautifully furnished living room. From there, continue through the sliding glass doors on to the screened ...

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Property Type

Cudjoe Key House

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Key West House
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom

$489

avg/night

$489
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Nassau Suite is a bi-level suite with a very spacious bedroom upstairs a king bed, TV, writing desk w/outlet for computer and chair, in-room safe, iron & ironing board complete with Bahama ceiling fan, A/C and colorful Caribbean artwork. The upstairs bathroom has a walk in shower.Downstairs in ...

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Property Type

Key West House

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Key West Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Beautifully renovated, this 2-bedroom, 2-bath penthouse offers stunning views of the Atlantic Ocean and Smathers Beach. The fabulous kitchen features stainless steel appliances and granite countertops. Enjoy breathtaking sunrises from the balcony, where you can awaken to morning reflections.The recently ...

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Property Type

Key West Condo

Featured review

"beautiful ocean view condo"

condo was very clean and on the top floor with vault ceilings. Check in process was seamless as well as checkout.

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Key Largo Estate
5 BR | 5.5 BA | Sleeps 17 | Quick View
Sleeps 17, 5 bedrooms, 5.5 bathrooms
2 reviews

$2800

avg/night

$2,800
avg per night
View Details

Key Amenities

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

About this property

Southern Diversion Estate Key Largo - Brand New private gated 1 acre estate on the ocean with private beach, tiki hut , tropical private pool and 105ft of deepwater dockage. Great location just 8 minutes from The Ocean Reef Club. Docks provide up to 100amp service and water. There is a deepwater channel ...

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Property Type

Key Largo Estate

Featured review

"Wonderful home for our large family!"

This is a great house. Lots of room for 6 adults and 6 youth age 12-6! The caretaker Joe was super helpful! Everything was perfect!

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

$360

avg/night

$360
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Perfectly situated in Old Town Key West. This quaint pool cottage is perfect for a couple with occasional visitors. beautifully decorated with amazing outside space to enjoy our island breezes and cool off in our pool. This beautiful property has been well maintained with a newly renovated Kitchen. Queen ...

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Property Type

Key West Cottage

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Key West Condo | On the beach
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pool
  • WiFi

About this property

Keys to Paradise: A 5-Star Beachside RetreatThis beautiful 3-bedroom, 2-bath condo is located in a private beachside resort, conveniently close to Old Town Key West and just steps away from the beach. It's also an easy bike ride to all that Key West has to offer.Keys to Paradise is a direct ...

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Property Type

Key West Condo

Featured review

"Amazing, Heaven, Can't wait to go back"

THE KEYS TO PARADISE CONDO IS SO WONDERFUL. The view is Breathtaking. The condo is well kept and clean. It has beautiful furnishings and distinctive artwork on the walls. The condo is in the perfect location,facing ...

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

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Buccaneer Boathouse! Pack your floral shirts, swimming gear and sandals and come on down to Little Torch Key in the beautiful Florida Keys. This lovely home is spacious with 2 bedrooms and 2 bathrooms. It offers a large open kitchen, dining and living area for everyone to hang-out and plan ...

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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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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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Tavernier House | On the beach
4 BR | 3 BA | Sleeps 15 | Quick View
Sleeps 15, 4 bedrooms, 3 bathrooms

$1700

avg/night

$1,700
avg per night
View Details

Key Amenities

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

About this property

An exclusive property with 300 feet of open ocean, private beach, dock, boat basin, ramp on Millionaires' Road. This property is approximately 5.5 acres of total privacy (contract will be for 3 out of 5 acres) with 3,000 square feet of quiet enjoyment for a romantic getaway or family trip with the ...

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Property Type

Tavernier House

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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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Summerland Key House
3 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 1 bathroom

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

No steps here! Looking for the perfect ground level home for your FL Keys vacation? Look no further, Casa Morada is the place for you!Florida Keys Vacation Rentals – Amazing canal front 3 bed conch style house located in prestigious community of Summerland Key Cove. It is the first canal from ...

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Property Type

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

$750

avg/night

$750
avg per night
View Details

Key Amenities

  • Pool
  • WiFi

About this property

3 Bedrooms, 3 Full Bathrooms, Backs to Community Pool, Sleeps up to 6This home was built in 2004. It has been well maintained and is ready for you to enjoy on your next vacation in Key West. You can stay in this 3 Bedroom home for less than the cost of one room in some local hotels. There is a nice ...

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Property Type

Key West House

Featured review

"Southern Charm with a boat slip!"

Our family had a wonderful time staying in this townhome style rental. We relaxed and enjoyed the views of the bay and marina from the back porch. The boat slip worked great for our rental boat. This ...

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

Distance to beach: 800 yards to Ft. Zachary Taylor State Park

$429

avg/night

$429
avg per night
View Details

Key Amenities

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

About this property

Envision yourself relaxing in a beautiful wood framed conch cottage with overhead fans lazily turning below the sloping tin roof in the heart of Old Town in Key West. This is the best value in Key West as it is no cookie cutter small rental condo but a private town home (one of only seven available for ...

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Property Type

Key West Cottage

Featured review

"Island Magic"

Great location! Great people! Very nice place that gave us memories of a lifetime! I’ll be returning soon!

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

$358

avg/night

$358
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Aaarrrghhhhhhh MATEY! Florida Keys Vacation Rentals – Looking for a perfect sunny get away in the beautiful Florida Keys? Blackbeard’s Bounty is just the place for you and your guests!This tropical oasis is located on Little Torch Key and is only 28 miles from Key West. Situated on a wide ...

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Property Type

Little Torch Key House

Featured review

"We hope to be back Loved our stay"

Great location for boating/Fishing Agua Azul is an amazing place great home to relax and chill out family had a amazing time

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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
4 BR | 3 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 3 bathrooms
3 reviews

$525

avg/night

$525
avg per night
View Details

Key Amenities

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

About this property

PLEASE INQUIRE WITHIN FOR ALL STAYS AND SPECIAL DEALS!!!OCEANFRONT Jewel in the Heart of Islamorada and on Tavernier Creek allows for easy access to everything the Upper Keys have to offer and direct Ocean and Bay access. This Open Water home HAS IT ALL. -Brand New (Sept 2017) Huge, heated ...

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Property Type

Islamorada House

Featured review

"Love this house"

Great location! Sunrises and sunsets were amazing. Easy location to open water, kids loved going out on boat. Fishing right off the dock. Lots of wildlife. Everyone loved the outdoor bathroom! Very convenient. ...

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

$50

avg/night

$50
avg per night
View Details

Key Amenities

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

About this property

Unit #179 - At the “Tree Top Paradise” we have spared no expense to make sure your vacation is not just a vacation but an experience of your life with a peak a boo view of the canal. This home is a fantastic 2 bedrooms (Queen beds) and a sleeper sofa and 2 baths. You have a large lovely screened ...

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Property Type

Cudjoe Key House

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

$587

avg/night

$587
avg per night
View Details

Key Amenities

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

About this property

When they say it's all about the location, this home says it all!By city ordinance, you must rent this property for 29 days or longer!!Welcome to this beautifully restored, remodeled second-floor 1933 Key West home on Caroline Street.A stairway decorated with wainscoting will lead you ...

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Property Type

Key West House

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

$116

avg/night

$116
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly

About this property

Kick back and relax in this Island vacation home. Or, enjoy the spacious deck located off the kitchen area, and take in the warm tropical breezes, canal and spectacular sunset skies. Fish from the dock or take advantage of the convenient boating access and cruise out to Looe Key, site of some of the best ...

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Property Type

Summerland Key House

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

$183

avg/night

$183
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful ocean front apartment with easy access to pool ,spa and beach. Dock with boat slips and tiki hut overlooking Atlantic Ocean. Community exercise room Master Bedroom overlooking the ocean Two bedrooms, two full baths. Gourmet equipped kitchen Laundry room Balcony with spiral stairs ...

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Property Type

Islamorada Apartment

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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
View Details

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

$259

avg/night

$259
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Pet friendly
  • Private pool
  • WiFi

About this property

Florida Keys Vacation Rentals – Come and enjoy a magnificent vacation with open water views at this beautiful Big Pine Key home. This home boasts décor by award winning Key West decorator and is super roomy, with three bedrooms and two bathrooms. A large, well-appointed eat-in kitchen will ...

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Property Type

Big Pine Key House

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Ramrod Key Cottage
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
1 review

$285

avg/night

$285
avg per night
View Details

Key Amenities

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

About this property

Newly renovated cottage with million dollar oceanfront views. The beautiful in ground pool will give the serenity you need for a relaxing escape.

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Property Type

Ramrod Key Cottage

Featured review

"Great view and nice pool Loc Loc Loc"

Very quiet location. The pool is very nice with a million dollar view. Prefect place for two of you to relax and chill out at the pool. This place is in a great location and has everything you will need ...

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

$266

avg/night

$266
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

Florida Keys Vacation Rentals – Need a private space to call home during your sunny stay in the Florida Keys? Conchy Joe’s is the place! This beautiful home has 3 bedrooms and 2 bathrooms. The interior is fully furnished and decorated in Florida Keys fashion with plenty of space for friends ...

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Property Type

Cudjoe Key House

Featured review

"Island getaway"

Always enjoy our stays in Keys when we find such a lovely place to have family come to join us. Some homes have a great location some have great amenities, but finding one like this, that has both is ...

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Key West Mobile home
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms
1 review

$200

avg/night

$200
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Located just 10 miles from Key West on beautiful Geiger Key. Cozy and comfortable canal front getaway perfect for the fisherman eager to explore the crystal blue waters of the Keys or the person wanting to experience all that Key West has to offer. Deep water with quick direct access to Atlantic Ocean. ...

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Property Type

Key West Mobile Home

Featured review

"Awesome Key West Getaway-We'll be back!"

This location is amazing just minutes to downtown Key West and a few minute idle by Boat to the Ocean(we brought our own boat and docked out back!) Had fun Snorkeling in crystal clear water, and even tried ...

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

$183

avg/night

$183
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy all the beauty the Florida Keys has to offer in this well-appointed, tastefully decorated 2 bedroom, 2 bath condominium located on the 4th floor overlooking Buttonwood Bay, at the Rock Harbor Club, Key Largo. This is a gated community offering a beautiful pool, tennis courts, bocce court, gorgeous ...

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Property Type

Key Largo Condo

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Key West Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$650

avg/night

$650
avg per night
View Details

Key Amenities

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

About this property

Bluegrass Seabbatical is a Spectacular 3 bedroom 2 bath oceanfront condominium at 1800 Atlantic. Enjoy the incredible ocean front view from all 3 bedrooms and the living room. This property is close to 2000 sq feet and can be your fantastic home away from home. Available for extended stays during the ...

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Property Type

Key West Condo

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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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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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Big Pine Key House
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

A get away to "Our Island Thing" will be unforgettable vacation for everyone. Huge 1,900 square-foot house with lots of room for the whole family and kids. Four bedrooms and two bathrooms, this two level concrete home is roomy and airy.The second floor has a huge kitchen, living and dining ...

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Property Type

Big Pine Key House

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

$343

avg/night

$343
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Paradise Palms! This amazing 3 bedroom home on Cudjoe Key is perfect for your next Florida Keys vacation! Tropical landscaping surrounds an inground pool that overlooks a beautiful canal...everything you could want and more! There is also large concrete dock for your boat, quick easy ocean ...

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Property Type

Cudjoe Key House

Featured review

"Excellent location & Super clean Home"

My family and I stayed for the month of June 2022 and this was the first time we had visited Cudjoe Key. The house was beautiful and VERY clean. The kitchen was well equipped with everything you needed ...

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

$989

avg/night

$989
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Great top floor 2 bedroom Condo on the Atlantic ocean with views of the ocean and courtyard. The property has a full size fully equipped kitchen with a washer/dryer. Both bedrooms and the living room have impact doors open to your private balcony. There is a King bed in the master bedroom and a queen ...

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Property Type

Key West Condo

Featured review

"New Year’s vacation"

Wanted to go to the Florida Keys, but this place popped up several times during my search. I’m so glad I chose this place. Breathe taking is the best word to use. Beautiful beach (7miles of it), nice ...

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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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$1484

avg/night

$1,484
avg per night
View Details

Key Amenities

  • Oceanfront
  • Pool
  • WiFi

About this property

Beautiful top floor ocean front 2 bedroom 2 bath condo at La Brisa in Key West. The property has a queen bed in each bedroom and the master has an en suite bathroom. Totally renovated Kitchen and a balcony with amazing Sunrise Views across Smathers Beach. The living room has a flat screen smart TV ...

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Property Type

Key West Condo

Featured review

"Vacation"

Very thing was good the condo was perfect and the pool was great the parking was close to the elevator

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Tavernier Mobile home
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
8 reviews

$160

avg/night

$160
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner

About this property

This property is located on a very unique spot. Very private. Too perfect to describe.During the day you could sunbathe while fishing for snappers, tarpon and lobsters from your private dock. Later on you may want to jump in for a swim or cruise the area on the kayak At early evening you may enjoy ...

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Property Type

Tavernier Mobile Home

Featured review

"Just amazing Keys experience!"

Where to start?? The property itself is located midway in the keys, offering short day trips as well as endless nearby attractions such as John Pennecamp Park, kayak/boat rentals, boat excursions, etc. ...

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Key Largo Mobile home
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

$233

avg/night

$233
avg per night
View Details

Key Amenities

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

About this property

Welcome to Lime Time! This exceptional Newly Remodeled two bedroom home is sitting right on the water, literally, of the Florida Bay in Key Largo. Unlike most of the neighboring construction, the water here is all around you, not 30 feet away. We have a large social deck off of an even larger screened ...

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Property Type

Key Largo Mobile Home

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

Distance to beach: 4 miles to Sombrero Beach

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

A Private And Convenient Piece of Paradise Awaits You In This Amazing 4 bedroom/ 3 bathroom Home Near Sombrero Beach. Our Home Is Located On A Deep Water Canal With Boat Access From The Yacht Club Boat Launch. ~KEY Z DREAMING~ Is Everything You Can Imagine With A Breathtaking Tiki Hut And Bar Located ...

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Property Type

Marathon House

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Key Largo Estate
7 BR | 5.5 BA | Sleeps 20 | Quick View
Sleeps 20, 7 bedrooms, 5.5 bathrooms
3 reviews

$800

avg/night

$800
avg per night
View Details

Key Amenities

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

About this property

Large, very spacious, beautifully appointed 7 BR home with breathtaking ocean views, large dock, pool, 2 jacuzzis, BBQ grill, 4 kayaks, large tiki, two fully equipped kitchens, all new appliances and major upgrades since Irma. Comfortably accommodates multiple families. Very private and secure with property ...

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Property Type

Key Largo Estate

Featured review

"Perfect house for families!! Amazing outdoor space!!"

We loved our stay at Casa Lorelane! We had 18 people and never once felt crowded. The living area on the second floor was amazing. The second kitchen on main floor made it easy to prepare food to enjoy ...

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Cudjoe Key Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$159

avg/night

$159
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

This super cozy, comfortable 2-bedroom, 2-bath vacation rental is located in the heart of Cudjoe Key, just minutes from the open ocean. Perfect for fishing, snorkeling, and diving enthusiasts, the home boasts easy access to some of the best spots in the Florida Keys.Relax and unwind in style after ...

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Property Type

Cudjoe Key Bungalow

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Islamorada Townhome
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms

$126

avg/night

$126
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Fully furnished 2 bedroom 1. 1/2 baths with balcony, heated pool, sauna and fitness room. Also a community room with flat screen and full kitchen, pool and ping pong. Beautiful ocean view from pool and community room. Huge ocean front dock for fishing, snorkeling and kayaking. WiFi , restaurants ...

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Property Type

Islamorada Townhome

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Key West Condo
Studio | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 0 bedrooms, 1 bathroom
5 reviews

Distance to beach: 0.5 miles to South Beach

$292

avg/night

$292
avg per night
View Details

Key Amenities

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

About this property

This Simonton Studio is neat, sweet and complete. * Pet friendly for additional flat fee of $90 *Cleaning fee of $70 is additional. * WiFi included * King size bed * Outdoor table and two chairs * spacious shower * excellent loctaion for walking Old Town * Duval Loop bus passes this adress ...

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Property Type

Key West Condo

Featured review

"Fantasic studio unit and a great location."

Very clean and well-equipped unit. It comes with cable tv and great internet. It is a great location, one block from Duval st.

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

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Make your memories at the Aloe House on Cudjoe Key! This home is located on a beautiful crystal clear canal with plenty of dockage for up to a 25 foot boat. The canals here provide great access to some of the best fishing in the Florida Keys. Enjoy boating, fishing or kayaking right from your back door.After ...

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Property Type

Cudjoe Key House

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

Distance to beach: 2 miles to Sombrero Beach

$353

avg/night

$353
avg per night
View Details

Key Amenities

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

About this property

A beautiful waterfront half duplex home in a tropical setting with views of the Gulf of Mexico and incredible sunsets. Recently renovated octagonal shaped home with wide open water views from every window. Newly furnished comfortable interior with all the amenities you'd expect. Brick pavers surround ...

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Property Type

Marathon House

Featured review

"Best trip EVER!"

Will definitely be back to this house. The house was perfect! We saw manatees, lots of sea turtles, tropical fish and caught a tarpon! The house is ideally located and very private. We had a fabulous two ...

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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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