Vacation Rentals & House Rentals in Florida Keys

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27 house rentals

New Rental Sombero Beach

Marathon Shores house

4 bedrooms / 5 bathrooms / sleeps 10

Match: Pool or snooker table

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Price per night from

$857

Real World MTV House Key West

Key West house

10 bedrooms / 6 bathrooms / sleeps 22

“Haha Buffalo, New York” This year while my friends and neighbors froze to death in Buffalo, my extended family and a few friends escaped the cold at the Real World MTV House in Key West. It was cold in Key West as well just 78 degrees, all the locals were complaining.and wore sweaters (haha). Everything was great and we laughed as we watched the weather on the TV at night up north. The 2 houses (main and Racket ball) are absolutely perfect for 20 guests. The property is huge . No complaints, we loved the paddle boards and kayaks, and how easy it was to put in the ocean behind the house and go!! Aric, the caretaker, gave us a few good tips for riding the paddle boards, fishing holes and restaurants. A nice quiet guy!!!

Responds fast! avg. 2 hours 19 minutes

Match: Pool or snooker table

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Price per night from

$1,805

WELCOME TO PARADISE! In the heart of Islamorada

Islamorada condo

1 bedroom / 1 bathroom / sleeps 5

Match: Pool or snooker table

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Price per night from

$149

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$87

Extraordinary waterfront custom home

Marathon Shores house

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$739

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 28 minutes

Match: Pool or snooker table

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Price per night from

$1,145

Paradise Found - Sandy Beach, Beachside Bar, Great Views, And Dock

Islamorada villa

3 bedrooms / 3 bathrooms / sleeps 6

Match: Pool or snooker table

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Price per night from

$402

Family vacation rental, kayak, pool, 50” dock

Key Largo house

3 bedrooms / 3 bathrooms / sleeps 10

Match: Pool or snooker table

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Price per night from

$173

Tropical Getaway 3 Bed/2 Bath walking Distance to the Beach

Marathon Shores house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$223

Sunrise Paradise 4 Bedrooms 4 Baths Luxury Home

Marathon house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$842

Wake up in Paradise! Florida Keys - Islamorada (6 month minimum rental)

Islamorada condo

2 bedrooms / 3 bathrooms / sleeps 4

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Price per night from

$112

Big Kahuna 5bed/4bath updated home with private pool & dockage

Marathon house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$408

Stunning Oceanfront Private Home - Best Value in the Upper Keys

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 32 minutes

Match: Pool or snooker table

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Price per night from

$201

Sunset at Manatee Oasis 3/2 Ground Level Home w/ Pool & 35` Dock

Marathon house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$391

Shangri-La 3/3 with private den, Pool & Dock

Marathon house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$621

Escape to Paradise

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

“Fabulous!!” We booked this beautiful house for our first week in the Keys. We had a group of adults and kids who went down for the week and we took our boat. This beautiful house had plenty of space for all of us and a ton of outside space to enjoy. The access to the water was easy on both the Gulf and Atlantic side. The amenities provided with the house or perfect. There was actually more than we usually find in a rental house. We had a few minor issues with the house that were taken care of very promptly by the owner. We will definitely be back next year.

Match: Pool or snooker table

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Price per night from

$241

Sunrise Waterfront Home

Key Largo house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 45 minutes

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Price per night from

$287

Pat's Beach House 2/2 w Dock & Cabana Club

Key Colony Beach house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$205

Sweet Retreat 4/3 Bath w Pool/spa & Dock

Marathon house

4 bedrooms / 3 bathrooms / sleeps 10

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$515

Little Piece of Paradise 3bed/2bath with cabana club & dockage

Key Colony Beach house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$266

Castaway 2/2 w 60' of Dock

Marathon house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$168

2 Bedroom, 2 Bath Condo with Kitchen, Living Room, Balcony, Pool, Parking,WiFi

Key West condo

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$248

Welcome to Paradise

Long Key townhouse

2 bedrooms / 3 bathrooms / sleeps 5

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Price per night from

$205

Florida Keys Vacation Villas Waterfront Family Friendly Pool Spa Deep Water Dock

Marathon villa

6 bedrooms / 5 bathrooms / sleeps 14

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Price per night from

$997

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$190

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$176

Great rentals within 20 miles that match your search

A Coastal Getaway 6/4.5 Bath w Pool, Dock & Kayaks

Sunset Point house

6 bedrooms / 5 bathrooms / sleeps 18

Responds fast! avg. 2 hours 29 minutes

Match: Pool or snooker table

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Price per night from

$332

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