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Grill
Wireless Internet
Air conditioning
Swimming pool

Private pool
Heated pool
Private indoor pool
Balcony or terrace
Washing machine
Jacuzzi or hot tub
Garden
Internet access
DVD player
Cot available
High chair
Sea view
Safe
Dishwasher
Children's pool
Shared outdoor pool (heated)
Shared outdoor pool (unheated)
Shared indoor pool
Private outdoor pool (heated)
Private outdoor pool (unheated)
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
Boat available
Housekeeping Included

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Pets allowed
Parking
Car not required
Children under 5

Smoking allowed
Non-Smoking property
Smoking - Ask
Elevator access
Wheelchair adapted
Wheelchair accessible

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Beach or lakeside relaxation
City breaks
Skiing – property near ski resort
Walking trips

Tennis in town
Nightlife
Water sports
Fishing
Waterfront
Golf within 30mins drive

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77 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

$766

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

$1,717

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

Match: Grill

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Price per night from

$172

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

$395

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

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

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

Match: Grill

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Price per night from

$622

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

Match: Grill

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Price per night from

$172

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

3 bedrooms
3 bathrooms

sleeps 7

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Price per night from

$1,949

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

Match: Grill

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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

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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

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Price per night from

$229

Coconut Cay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

Match: Grill

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Price per night from

$208

Hawkins Heaven

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$178

Buccaneer Boathouse

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 6

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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

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Price per night from

$259

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$184

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

Match: Grill

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Price per night from

$174

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

Match: Grill

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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: Grill

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Price per night from

$224

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$253

Grouper Therapy

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$214

Sun Kissed

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$158

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$4,015

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

Stock Island house

4 bedrooms
3 bathrooms

sleeps 11

Match: Grill

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Price per night from

$801

Viewing 38 of 77
rentals in Summerland Key

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Summerland Key Rentals

Per night

77 Houses

Viewing 38 of 77rentals in Summerland Key

Also consider

Viewing 38 of 77
rentals in Summerland Key