Florida Keys Vacation Rentals

The Florida Keys - Islamorada, Cudjoe Key, Key West, Marathon and more

Key West Condo

2 Bed 1 Bath 6-Jan Sleeps

Key West Roof Top Condo Property Id: 293087

Rental Info:

Minimum Stay: 1 Nights

Water Front

Roof Top Waterfront Condo 2 bedroom, 1 bath, sleeps 6 Key West Florida MM10

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summerland keys

5 Bed 4 Bath 10-Jan Sleeps

Summerland Estate Property Id: 271701

Rental Info:

From $ 3000 p/week
Minimum Stay: 7 Nights

Smoking Allowed
Water Front

Gorgeous ocean front 5 bedroom 4 bath pool home, dock, hottub, pooltable, private. tiki hut with bar

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Waterfront Home

1 Bed 1 Bath 3-Jan Sleeps

Pelican Harbour Key Largo Property Id: 235638

Rental Info:

Minimum Stay: 5 Nights

Water Front

Pelican Harbour Key Largo 1 bed - 1 bath - sleeps 3 Key Largo Florida

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Islamorada Rental

0 Bed 1 Bath 4-Jan Sleeps

Islamorado Studio Rental Property Id: 121530

Rental Info:

Minimum Stay: 7 Nights

Water Front

Islamorada Studio Rental Islamorada, Florida Studio, 1 bath, sleeps 3

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Key Colony Beach

2 Bed 2 Bath 1-6 Sleeps

Key Colony Beach Property Id: 177344

Rental Info:

Minimum Stay: 7 Nights

Key Colony Beach Pet Friendly 2 bed, 2 bath, sleeps 6

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Waterfront Condo

2 Bed 2 Bath 6-Feb Sleeps

Key Colony Waterfront Condo Property Id: 106890

Rental Info:

Minimum Stay: 7 Nights

Water Front

Key Colony Waterfront Condo 2 bed, 2 bath, sleeps 6 Key Colony Beach, Marathon, FL

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Waterfront Townhome

3 Bed 2.5 Bath 8-Feb Sleeps

Key Colony Waterfront Townhome Property Id: 182991

Rental Info:

Minimum Stay: 7 Nights

Water Front

Key Colony Waterfront Townhome 3 bed, 2.5 bath, sleeps 8 Key Colony Beach, Marathon, FL

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Waterfront Home

3 Bed 5 Bath 8-Feb Sleeps

Layton House Long Key Property Id: 126575

Rental Info:

Minimum Stay: 7 Nights

Water Front

Layton House Long Key 3 bed, 5 bath, sleeps 8 Long Key, FL

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Marathon Canal Home

2 Bed 1 Bath 6-Jan Sleeps

Marathon Canal Home Property Id: 388916

Rental Info:

Minimum Stay: 7 Nights

Marathon Canal Home Rental 2 Beds, 1 Baths, Sleeps 6 Marathon Key, Florida Keys, Florida

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Key West VRBO

1 Bed 1.5 Bath 1-2 Sleeps

Ann Street Cottage Property Id: 168127

Rental Info:

Minimum Stay: 1 Nights

Ann Street Cottage 1 bed, 1.5 bath, sleeps 2 Key West Florida

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waterfront condo

2 Bed 2 Bath 5-Jan Sleeps

Futura Yacht Club Property Id: JS021

Rental Info:

From $ 800 p/week
Minimum Stay: 7 Nights

Water Front

Futura Yacht Club 2 bedrooms - 2 baths - sleeps 5 Islamorada - Florida Keys

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Waterfront Estate

3 Bed 2 Bath 8-Jan Sleeps

Breezeswept Villa Property Id: RS604

Rental Info:

From $ 1250 p/week
From $ 3950 p/month
Minimum Stay: 28 Nights

Breezeswept Villa Wonderful Florida Keys - 3 Bedroom Estate Ocean front community with Waterfront Homes

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Gulf Front

2 Bed 2.5 Bath 6-Jan Sleeps

Islamorada Gulfront Townhome Property Id: FKT

Rental Info:

From $ 2995 p/month
Minimum Stay: 30 Nights

Water Front

Florida Keys Townhome Islamorada, Florida Keys 2 bed - 2 1/2 bath - sleeps 6

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Key West Condo

1 Bed 1 Bath 4-Jan Sleeps

Key West Condo Rental Property Id: 7030624h

Rental Info:

Minimum Stay: 28 Nights

Key West Rental Condo 1 bed, 1 bath, sleeps 4 Key West, Florida

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Cudjoe Key Rental

2 Bed 2 Bath 1-6 Sleeps

Cudjoe Key Dock Home Property Id: 234389

Rental Info:

Minimum Stay: 2 Nights

Water Front

Wonderful Cudjoe Key Boat Dock Home 2 bed, 2 bath, sleeps 6 Cudjoe Key, Florida

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Moon Bay Condo

2 Bed 1.5 Bath 6-1 Sleeps

Moon Bay Key Largo Property Id: 118645

Rental Info:

Minimum Stay: 3 Nights

Water Front

Key Largo Getaway 2 bed room, 1 1/2 bath room, Sleeps Key Largo Florida

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Waterfront Cottage

2 Bed 1 Bath 4-Jan Sleeps

Key Largo Cottage Property Id: 225990

Rental Info:

Minimum Stay: 3 Nights

Water Front

Key Largo cottage 2 bed, 1 bath, sleeps four key Largo, Florida

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Key Largo Rental

2 Bed 2 Bath 1-4 Sleeps

Key Largo Rental Property Id: 379968

Rental Info:

Minimum Stay: 3 Nights

Water Front

Key Largo Rental 2 bed, 2 bath, sleeps 4 Key Largo, Florida

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Key West

2 Bed 2.5 Bath 6-Jan Sleeps

Coral Hammock Rental Key West Property Id: 40061h

Rental Info:

Minimum Stay: 5 Nights

Water Front

Coral Caribe Key West Rental 2 bed - 2.5 bath - sleeps six Key West Florida

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2 Bed 1 Bath 4-1 Sleeps

Bucaneer Point Key Largo Property Id: 270741

Rental Info:

Minimum Stay: 3 Nights

Water Front

Buccaneer Point Key Largo 2 bed, 1 bath, sleeps four Key Largo, Florida

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Futura Yacht Club

2 Bed 2 Bath 6-Jan Sleeps

Futura Yacht Club - Islamorada Property Id: 7053653h

Rental Info:

Minimum Stay: 28 Nights

Water Front

Futura Yacht Club 2 bed - 2 bath - sleeps 6 Islamorada - Florida Keys

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Key West Townhome

2 Bed 1.5 Bath 5-Jan Sleeps

Key West Golf Club Townhome Property Id: 7048520h

Rental Info:

Minimum Stay: 1 Nights

Water Front

Key West Golf Club Townhome Key West Vacation Home 2 bed, 1 1/2 bath, sleeps 5

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Shipyard Condo

2 Bed 1 Bath 4-1 Sleeps

Shipyard Condo Key West Property Id: TA-Charming

Rental Info:

Minimum Stay: 7 Nights

Water Front

Charming Shipyard Condo Key West, Florida Two Bed - One Bath - Sleeps 4

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Coral Coast

5 Bed 4 Bath 10-Jan Sleeps

Coral Coast Key Largo Home Property Id: 7073250h

Rental Info:

Minimum Stay: 5 Nights

Water Front

Coral Coast Key Largo Home 5 bed, 4 bath, sleeps 10 Key Largo, Florida

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Summerland Key

5 Bed 3 Bath 1-12 Sleeps

Summerland Canal Pool Home Property Id: 341950

Rental Info:

Minimum Stay: 7 Nights

Water Front

Summerland Key Pool Home 5 bed, 3 bath, sleeps 12 Summerland Key, Florida

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Key Largo

3 Bed 2 Bath 8-Jan Sleeps

Buttonwood Bay Ground Floor Property Id: 343418

Rental Info:

Minimum Stay: 30 Nights

Water Front

Buttonwood Bay Ground Floor Rental 3 Bed, 2 bath, sleeps 8 Key Largo, Florida

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Key West Cottage

1 Bed 1 Bath 4-Jan Sleeps

Pet Friendly Key West Cottage Property Id: 391123

Rental Info:

Minimum Stay: 7 Nights

Key West Pet Friendly Cottage Studio, 1 bath, sleeps 4 Key West, Florida

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Key West studio

0 Bed 1 Bath 1-4 Sleeps

Galleon Resort Old Town Property Id: 169027

Rental Info:

Minimum Stay: 1 Nights

Water Front

Galleon Resort Old Town Studio, 1 bath, Sleeps 4 Key West, Florida

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key west

1 Bed 1 Bath 1-2 Sleeps

Ann Street Tranquility Property Id: 168126

Rental Info:

Minimum Stay: 1 Nights

Ann Street Tranquility Cottage 1 bed, 1 bath, sleeps 2 Key West Florida Cottage

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Ocean View

3 Bed 2 Bath 1-6 Sleeps

La Brisa Key West Property Id: 168237

Rental Info:

Minimum Stay: 28 Nights

Water Front

La Brisa Key West 3 bed, 2 bath, sleeps 6 Key West, Florida

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Oceanview

1 Bed 1 Bath 1-2 Sleeps

Casa Atlantica Key West Property Id: 168155

Rental Info:

Minimum Stay: 1 Nights

Water Front

Casa Atlantica Key West 1 bed, 1 bath, sleeps 2 Key West, Florida

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Key West cottage

3 Bed 3 Bath 1-6 Sleeps

Key West Vacation Cottage Property Id: 168137

Rental Info:

Minimum Stay: 7 Nights

Key West Vacation Cottage 3 bed, 3 bath, sleeps 6 Key West, Florida

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Craig & Cindy's Key West Truman Annex Porter House (4 bedroom with private pool)

House

4 Bed 3 Bath Sleeps 8

Craig & Cindy's Key West Truman Annex Porter House (4 bedroom with private pool) Key West

The two story Truman Annex Porter House is the largest of our Key West properties and features 4 bed

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Coral Cove Resort - Fisherman's Dream

House

4 Bed 2 Bath Sleeps 8

Coral Cove Resort - Fisherman's Dream Islamorada

Enjoy camaraderie with family and friends in this well-appointed, four-bedroom, ranch-style house in

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Luxury RV Living at the Lobster Shack

Recreational_vehicle

1 Bed 1 Bath Sleeps 6

Luxury RV Living at the Lobster Shack Key Largo

The "Lobster Shack" is a 37 foot RV located in Key Largo Kampground, just minutes from John Pennekam

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Hyatt Sunset Harbor   (1 week January 14 to 21, 2018)

Studio

1 Bed 1 Bath Sleeps 2

Hyatt Sunset Harbor (1 week January 14 to 21, 2018) Key West

You will love this studio(unit 224A) in the premier timeshare/condo property in Key West right on t

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Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool

Cottage

4 Bed 2 Bath Sleeps 7

Chick-a-Pea's Cottage: Pet-Friendly with Fenced Yard! Parking & Private Pool Key West

The house is a traditional Key West cottage that has undergone a complete renovation in 2012. The ch

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MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West

Condo

2 Bed 1 Bath Sleeps 5

MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West Key West

This wonderful 2 bedroom downstairs unit is owner's second home and has just been beautifully and pr

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Very Rare- Ocean Breeze Suites-3 Bd, 3 Bath with loft  Sleeps 10

Condo

3 Bed 3 Bath Sleeps 10

Very Rare- Ocean Breeze Suites-3 Bd, 3 Bath with loft Sleeps 10 Key West

The Galleon Resort in Key West is a Perfect Resort for you, your Guests and your Family. The unit is

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Beach House with Ocean View

Condo

1 Bed 0 Bath Sleeps 4

Beach House with Ocean View Key West

If you are looking to stay in accommodations of high standards. This is the one for you! As you ente

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The Conch Farmhouse

Condo

2 Bed 1 Bath Sleeps 4

The Conch Farmhouse Key West

Hi there! We have just renovated our entire home and know you'll thoroughly enjoy yourself here. We

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Casa Amor - 3BR Residence   2 Blocks from Duval Street

House

3 Bed 3 Bath Sleeps 8

Casa Amor - 3BR Residence 2 Blocks from Duval Street Key West

Welcome to Casa Amor, our love nest for ten years has been converted into a vacation rental for you.

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Cute

House

2 Bed 1 Bath Sleeps 6

Cute "Keysie" cottage in gated community with tons of amenities! Cudjoe Key

Recently remodeled 2/1 midrise home in a gated community! Features a brand new grill, deck with seat

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JASMINE PLACE -Private Old Town Pool Home

House

2 Bed 2 Bath Sleeps 4

JASMINE PLACE -Private Old Town Pool Home Key West

Jasmine Place is known for proximity and history throughout Key West. This enchanting home ideally l

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Tropical Custom Home with Gorgeous Sunset Views - available December 1, 2017

House

3 Bed 2 Bath Sleeps 6

Tropical Custom Home with Gorgeous Sunset Views - available December 1, 2017 Lower Sugarloaf Key

Enjoy a truly unique Florida Keys experience in this three-bedroom, two-bath home with a large tropi

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Flip Flop Retreat Townhome in Quiet Convenient Location

Townhome

2 Bed 2 Bath Sleeps 5

Flip Flop Retreat Townhome in Quiet Convenient Location Key West

Two bedroom, 2.5 bath townhome in Truman Annex two blocks to Duval Street. Quiet, clean, comfortabl

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Waterfront Gem in Shark Key

House

2 Bed 2 Bath Sleeps 4

Waterfront Gem in Shark Key Key West

This beautiful waterfront home in the private gated community of Shark Key has recently undergone a

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Tropical Islamorada Bungalow with pool, beach cruiser bikes, and free Wi-Fi

House

2 Bed 1 Bath Sleeps 4

Tropical Islamorada Bungalow with pool, beach cruiser bikes, and free Wi-Fi Islamorada

To all of our guests who have posted reviews: Thank you! We are very grateful to all of you for taki

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Pet Friendly Houseboat at the Beautiful Stock Island Marina Village in Key West

House_boat

1 Bed 1 Bath Sleeps 2

Pet Friendly Houseboat at the Beautiful Stock Island Marina Village in Key West Key West

The Gray Snapper is one of five 1 BR /1 BA floating houses located at Stock Island Marina Village.

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Quiet, Quaint and 2.5 blocks off of Duval St!

Studio

0 Bed 1 Bath Sleeps 2

Quiet, Quaint and 2.5 blocks off of Duval St! Key West

Quiet, quaint and conveniently located in the heart of key west. This small condo is a great place

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Cozy studio in Key Largo

Studio

0 Bed 1 Bath Sleeps 2

Cozy studio in Key Largo Key Largo

Winter or any time vacation studio on the water in Key Largo, Very tropical studio in the heart of K

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Harbour Place 115 in Truman Annex Key West

Condo

2 Bed 2 Bath Sleeps 6

Harbour Place 115 in Truman Annex Key West Key West

Harbor Place is one of the most prestigious properties in Key West!This unit offers breath taking wa

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More Florida Keys Vacation Rentals



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The Florida Keys offers up more fishing than one can possibly take in on just one trip. The harbor and surrounding areas are home to a plethora of fishing, tour and attraction boats. Whether you are looking for deep sea fishing, dolphin cruises or a fine dinner at sea, the Florida Keys and its fleet of pleasure boats will have what you need.

Also available throughout the florida Keys is an assortment of crafts, antiquing, site seeing, historical forts and settlements. The hardest part of any Florida Keys Vacation is figuring out what you will have time for, but have no fear, the Florida Keys will be here for your next trip so plan accordingly.