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Balcony or terrace
Wireless Internet
Air conditioning
Swimming pool

Private pool
Heated pool
Private indoor pool
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Grill
Fireplace
Cot available
Sea view
Safe
Dishwasher
Children's pool
Shared outdoor pool (heated)
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
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Pool or snooker table
Ceiling Fans
Clothes dryer
Games room
Table tennis
Cribs
Swing set or jungle gym
Fax machine
Linen provided
Iron
Hair dryer
Stove
Fridge
Freezer
Microwave
Towels provided
Video player
Bicycles available
Climbing frame
Trampoline
Private fishing lake or river
Staffed property
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Housekeeping Included

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Pets
Pets allowed
Parking
Car not required

Children under 5
Smoking allowed
Non-Smoking property
Smoking - Ask
Wheelchair adapted
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Beach or lakeside relaxation
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49 Houses

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Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Balcony or terrace

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Price per night from

$448

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$517

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

Summerland Key house

5 bedrooms
5 bathrooms

sleeps 10

Match: Balcony or terrace

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Price per night from

$766

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

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 10

Match: Balcony or terrace

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Price per night from

$1,722

Luxury Oceanview Pool Eco-friendly Villa Near Key West

Summerland Key villa

4 bedrooms
2 bathrooms

sleeps 12

Match: Balcony or terrace

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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

Match: Balcony or terrace

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Price per night from

$172

Sailfish Manor

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 9

Match: Balcony or terrace

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Price per night from

$384

salty slumber get away

Summerland Key house

4 bedrooms
3 bathrooms

sleeps 6

Match: Balcony or terrace

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Price per night from

$396

The Pointe

Summerland Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Balcony or terrace

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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

Match: Balcony or terrace

All filters match

Price per night from

$174

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

Match: Balcony or terrace

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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

Match: Balcony or terrace

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Price per night from

$179

Keys Life

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Balcony or terrace

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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

Match: Balcony or terrace

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Price per night from

$144

Great rentals within 20 miles that match your search

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

Match: Balcony or terrace

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Price per night from

$1,950

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

Match: Balcony or terrace

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Price per night from

$775

Two Story Stilt Home with a Wraparound Deck in a Tropical Paradise in Fl Keys

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Balcony or terrace

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Price per night from

$210

Home with Open Ocean,Spectacular Sunset views & Private Launch (28 day rentals)

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Balcony or terrace

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Price per night from

$229

Coconut Cay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$208

Hawkins Heaven

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Balcony or terrace

All filters match

Price per night from

$178

Buccaneer Boathouse

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

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Price per night from

$141

$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

Match: Balcony or terrace

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Price per night from

$259

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

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Price per night from

$184

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Balcony or terrace

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Price per night from

$174

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

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Price per night from

$171

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

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$224

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

Match: Balcony or terrace

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Price per night from

$253

Sun Kissed

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$158

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

Match: Balcony or terrace

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Price per night from

$801

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

Big Pine Key house

3 bedrooms
2 bathrooms

sleeps 10

Match: Balcony or terrace

All filters match

Price per night from

$775

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

Cudjoe Key house

4 bedrooms
4 bathrooms

sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$517

All-Inclusive Yacht Margarita Flaca: Marina OR Anchor on the Ocean: Free Charter

Stock Island yacht

1 bedroom
1 bathroom

sleeps 6

Match: Balcony or terrace

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Price per night from

$263

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 56 minutes

Match: Balcony or terrace

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Price per night from

$517

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 8

Match: Balcony or terrace

All filters match

Price per night from

$218

Cassie's Paradise

Sugarloaf Key house

5 bedrooms
4 bathrooms

sleeps 10

Match: Balcony or terrace

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Price per night from

$5,733

Sharkys Island Paradise

Big Pine Key house

5 bedrooms
3 bathrooms

sleeps 12

Match: Balcony or terrace

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Price per night from

$259

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. 2 hours 26 minutes

Match: Balcony or terrace

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Price per night from

$546

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Balcony or terrace

All filters match

Price per night from

$328

Viewing 38 of 49
rentals in Summerland Key

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Summerland Key Rentals

Per night

49 Houses

Viewing 38 of 49rentals in Summerland Key

Also consider

Viewing 38 of 49
rentals in Summerland Key