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Air conditioning
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Private pool

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Private indoor pool
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Cot available
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Pets allowed
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Skiing – property near ski resort
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Golf within 30mins drive
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51 apartments

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Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

4 bedrooms
2 bathrooms

sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

Match: Private outdoor pool (unheated) Pets allowed

All filters match

Price per night from

$544

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Private outdoor pool (unheated) Pets allowed

All filters match

Price per night from

$701

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

Match: Private outdoor pool (unheated) Pets allowed

All filters match

Price per night from

$517

$145 per night for months of Sep-Nov on Canal (fits 25-28 ft boat) and Pool.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Pets allowed, Private outdoor pool (unheated)

1 of 2 filters match

Price per night from

$259

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$318

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$288

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$141

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$148

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$268

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$144

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$151

Margarita Villa

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$189

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$236

Pirate's Cove

Cudjoe Key house

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$118

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$414

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$121

Coral House

Ramrod Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$218

Island Chalet

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$161

Conch Out

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$194

Coconut Cay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$208

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$174

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$171

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$234

Tranquility in Paradise - Cudjoe

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$218

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$184

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$384

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$114

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$623

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$287

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 7

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$308

Hogfish Retreat

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$178

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$1,721

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$253

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$224

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$231

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$775

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

3 bedrooms
3 bathrooms

sleeps 8

Responds fast! avg. 24 minutes

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$402

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Private outdoor pool (unheated), Pets allowed

1 of 2 filters match

Price per night from

$574

Viewing 38 of 51
rentals in Big Pine Key

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Vacation Rentals & Apartments in Big Pine Key

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51 apartments

Viewing 38 of 51rentals in Big Pine Key

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Viewing 38 of 51
rentals in Big Pine Key