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Washing machine
Wireless Internet
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Jacuzzi or hot tub
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Cot available
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Staffed property
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Pets allowed
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Beach or lakeside relaxation
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76 Houses

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Hogfish Hideout

Summerland Key house

3 bedrooms
2 bathrooms

sleeps 8

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Price per night from

$378

Salty Retreat

Summerland Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$446

Family Friendly House In Paradise

Summerland Key house

5 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$514

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

$761

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

$698

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

$382

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

$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

$230

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

$233

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

Fandango

Cudjoe Key house

5 bedrooms
3 bathrooms

sleeps 14

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Price per night from

$619

Charming Elevated Waterfront Home

Big Pine Key house

1 bedroom
1 bathroom

sleeps 4

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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

$1,939

Waterfront Cozy Cottage with Boat Ramp and Dock!

Little Torch Key cottage

2 bedrooms
1 bathroom

sleeps 6

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Price per night from

$456

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

8 bedrooms
5 bathrooms

sleeps 20

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Price per night from

$798

Conch House - Dock Your Boat

Little Torch Key house

4 bedrooms
4 bathrooms

sleeps 7

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Price per night from

$770

Buccaneer Boathouse

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$140

Cameron's Luxury Waterfront Estate with Dockage

Stock Island house

3 bedrooms
2 bathrooms

sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$514

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

$209

Lower Keys Retreat.....

Big Pine Key house

3 bedrooms
3 bathrooms

sleeps 8

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Price per night from

$251

Coconut Cay

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$207

Hawkins Heaven

Cudjoe Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$177

Grouper Therapy

Little Torch Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$213

Latitude Adjustment

Little Torch Key house

2 bedrooms
2 bathrooms

sleeps 4

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Price per night from

$173

Water's Edge

Big Pine Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$170

Pelican Perch

Cudjoe Key house

3 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$183

$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

$257

Sun Kissed

Ramrod Key house

2 bedrooms
2 bathrooms

sleeps 6

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Price per night from

$157

80' luxury yacht

Stock Island house

3 bedrooms
4 bathrooms

sleeps 6

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Price per night from

$3,993

Viewing 38 of 76
rentals in Summerland Key

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Summerland Key Rentals

Per night

76 Houses

Viewing 38 of 76rentals in Summerland Key

Also consider

Viewing 38 of 76
rentals in Summerland Key