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Wireless Internet
Air conditioning
Swimming pool
Private pool

Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
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Grill
Cot available
Sea view
Safe
Dishwasher
Satellite TV
Children's pool
Games room
Table tennis
Pool or snooker table
Fax machine
Shared outdoor pool (unheated)
Clothes dryer
Private outdoor pool (unheated)
Private outdoor pool (heated)
Shared indoor pool
Shared outdoor pool (heated)
Cribs
Ceiling Fans
Video player
Climbing frame
Boat available
Fridge
Central heating
Stereo system
Kettle
Toaster
Iron
Hair dryer
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Staffed property
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Linen provided
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Swing set or jungle gym
Trampoline
Private fishing lake or river
Housekeeping Included

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Pets
Pets allowed
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Car not required

Children under 5
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Non-Smoking property
Smoking - Ask
Wheelchair adapted
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Beach or lakeside relaxation
Skiing – property near ski resort
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Horse riding
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Golf within 30mins drive
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119 houses

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Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Match: Rental types Shared outdoor pool (heated)

All filters match

Price per night from

$5,720

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

2 bedrooms
1 bathroom

sleeps 4

Match: Rental types Shared outdoor pool (heated)

All filters match

Price per night from

$1,140

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$114

30% off now till March!!! Direct Atlantic Ocean front private boat ramp dock.

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$161

Tropical Paradise Oceanfront Home with Pool

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

“The Perfect Little Get away” We (my husband and I and our 1 year-old) stayed at the Tropical Paradise Home for a week with another couple; and it was the perfect amount of space to enjoy each other's company but still have our own private areas. The house was very, very clean when we checked in and we immediately felt at home. The pictures we had seen on-line did accurately reflect the rental's and amenities. The kitchen was great and we ate most of our meals on the screened in porch. We felt very secluded at the end of the street in our own tropical paradise. The vegetation and landscaping around the house is so beautiful. We all enjoyed time reading in the hammock, kayaking from our own backyard, and cooling off in the pool. We also enjoyed the beautiful sunrise every morning thanks to the baby. :) The owner is very friendly and left a packet of activities and restaurants near-by that she recommended. We enjoyed the restaurant Square Grouper for lunch or dinner (less than 5 mins away) and also enjoyed stand-up paddle boarding with sup Key West. We rented a full size crib from Baby Chick Rentals and they had the crib set up before we arrived. We also enjoyed driving into Key West for shopping/bars/and more restaurants. The drive to Key West is about 25 mins. We would definitely recommend the Tropical Paradise Home and we would stay there again!

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$573

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$621

Bay Pointe

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$203

Cove Isles

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$197

Breeze Swept

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$267

Bow Channel Manor

Sugarloaf house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$257

Blue Lagoon

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$317

Manatee Bay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$150

Island Time 1 (half of duplex)

Big Pine Key house

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$140

Casa Turquesa

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$287

Our Island Thing

Big Pine Key house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$277

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms
1 bathroom

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$147

Lafitte Landing

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$143

South Point Shores

Sugarloaf house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$230

Pirate's Cove

Cudjoe Key house

2 bedrooms
1 bathroom

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$117

Margarita Villa

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$188

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms
2 bathrooms

sleeps 10

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$235

Quiet Waters

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$160

Coral House

Ramrod Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$217

St. Croix

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$120

Villa Cayo

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$413

Big Torch Retreat

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$163

Pirates Pointe

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$173

Island Chalet

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$160

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$172

Conch Out

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$193

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$143

Bahia Azul

Ramrod Key house

4 bedrooms
2 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$268

Key West--20 min, Stunning Views, Private, Ocean Access, Spacious, Resort-like

Summerland Key house

5 bedrooms
5 bathrooms

sleeps 10

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$764

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

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$287

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms
5 bathrooms

sleeps 20

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$801

Hogfish Retreat

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$178

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

1 of 2 match: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$773

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: Shared outdoor pool (heated), Rental types

1 of 2 filters match

Price per night from

$573

Viewing 38 of 119
rentals in Summerland Key

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Houses Summerland Key

Per night

119 houses

Viewing 38 of 119rentals in Summerland Key

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Viewing 38 of 119
rentals in Summerland Key