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Grill
Wireless Internet
Air conditioning
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Private pool
Heated pool
Private indoor pool
Balcony or terrace
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Jacuzzi or hot tub
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DVD player
Cot available
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Sea view
Safe
Dishwasher
Children's pool
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Shared outdoor pool (unheated)
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Pool or snooker table
Ceiling Fans
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Cribs
Swing set or jungle gym
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Linen provided
Iron
Hair dryer
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Fridge
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Microwave
Towels provided
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Bicycles available
Climbing frame
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Private fishing lake or river
Staffed property
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Pets allowed
Parking
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Children under 5

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Beach or lakeside relaxation
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Skiing – property near ski resort
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Tennis in town
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Golf within 30mins drive

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78 Houses

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Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Grill

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Price per night from

$379

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$448

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

Summerland Key house

5 bedrooms
5 bathrooms

sleeps 10

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Price per night from

$765

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

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Price per night from

$1,720

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

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Price per night from

$700

Key Blessing: Experience the Keys Life at This Charming 3BR Canal Front Home, Do

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$172

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

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Price per night from

$384

Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Do

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 10

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$168

Casa Rosada: Cudjoe Gardens Canal Front Retreat, Pool, Tiki, Deep Dockage & Rapi

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$296

The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock &

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$180

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

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Price per night from

$396

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$231

Blue Fish Point: Tranquil, Luxurious Waterfront Oasis, Amazing Sunsets, Pool, Ti

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$174

Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Bre

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

Oceanview Cottage: Embrace Island Living with Sandy Toes and Breathtaking Open W

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$172

The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room fo

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$174

Anchors Aweigh: Amazing Oceanfront Views, Dock, Pool, Tiki, Space for Multiple F

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 12

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$179

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$234

The Hideaway: Discover and Lose Yourself! Newly Decorated Canal Front Home, Dock

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 2 hours 34 minutes

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Price per night from

$144

Great rentals within 20 miles that match your search

Fisherman's Paradise in the Heart of Big Pine Key

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$114

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!

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Price per night from

$574