Vacation Rentals & House Rentals in Florida Keys

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28 house rentals

Waterfront home on canal with Tiki hut and amazing water views!

Little Torch Key house

2 bedrooms / 1 bathroom / sleeps 7

Responds fast! avg. 39 minutes

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Price per night from

$82

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

Cudjoe Key cottage

2 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$184

Incredible Luxury Home with Waterfront!! Paradise

Islamorada house

5 bedrooms / 6 bathrooms / sleeps 12

Responds fast! avg. 2 hours 40 minutes

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Price per night from

$1,390

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

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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

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Price per night from

$149

THIS IS IT! Magnificent Oceanfront Paradise! WE ARE OPEN!!

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$163

Beautiful Captain's Cove

Islamorada villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$373

100' Private Beach Front Ocean Front Estate

Islamorada house

4 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 2 hours 28 minutes

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Price per night from

$1,145

IMMACULATE OCEAN VIEW CONDO AT SEAGULLS

Tavernier apartment

1 bedroom / 1 bathroom / sleeps 4

Responds fast! avg. 1 hour 54 minutes

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Price per night from

$172

ISLAMORADA Waterfront GREEN IVIS PARADISE Min 28 Ngts. Max 10 ppl. 26% Disc >1mo

Islamorada house

3 bedrooms / 2 bathrooms / sleeps 10

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Price per night from

$391

PARADISE IN KEY LARGO Townhouse

Key Largo townhouse

2 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$207

Blue Dolphin Private Oceanfront 1.8 acre Estate on Millionaire's Row with Pool

Islamorada house

5 bedrooms / 4 bathrooms / sleeps 12

Responds fast! avg. 1 hour 23 minutes

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Price per night from

$788

Very Nice 3 Bedroom Home With Large Lot!

Tavernier house

3 bedrooms / 2 bathrooms / sleeps 5

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Price per night from

$81

Family vacation rental, kayak, pool, 50” dock

Key Largo house

3 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$173

Pink Flamingo 2bed/3bath condo with shared pool

Marathon condo

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$209

Sailor's Delight 1bed/2bath condo with shared pool

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$152

Salty Dog 3bed/2bath condo with shared pool

Marathon condo

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$249

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.

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Price per night from

$241

Buttonwood Bay Key Largo Waterfront Townhouse

Key Largo apartment

2 bedrooms / 3 bathrooms / sleeps 8

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Price per night from

$176

Stunning Oceanfront Private Home - Best Value in the Upper Keys

Key Largo house

4 bedrooms / 4 bathrooms / sleeps 8

Responds fast! avg. 32 minutes

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Price per night from

$201

Salty Dog efficiency size condo with shared pool & dockage

Marathon condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$124

Pink Flamingo 1bed/2bath condo with shared pool

Marathon condo

1 bedroom / 2 bathrooms / sleeps 4

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$150

Pink Flamingo Efficiency condo with shared pool

Marathon condo

2 bedrooms / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 29 minutes

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Price per night from

$151

Oceanfront Islamorada Condo with Huge T-Dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$153

75651 Overseas Hwy Islamorada Fla Keys Oceanfront

Matecumbe Key apartment

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$132

Oceanfront 2/2 Condo in Beacon Reef - Free boat dock

Islamorada condo

2 bedrooms / 2 bathrooms / sleeps 4

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Price per night from

$287

Beautiful Oceanfront, heated pool, free wifi

Islamorada house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 10 minutes

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Price per night from

$431

Great rentals within 20 miles that match your search

NEW LISTING! Oceanfront townhome w/shared pool, hot tub & more on-site amenities

Sunset Point townhouse

4 bedrooms / 4 bathrooms / sleeps 10

Responds fast! avg. 40 minutes

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Price per night from

$574

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