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Summerland Key Rentals

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124 Results

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Price: high to low

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124 Houses

Blue vacation home, water front, boat dock, heated private Pool.

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$556

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$220

Hogfish Hideout

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$287

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$476

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$151

Salty Retreat

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$447

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 2 hours 30 minutes

Price per night from

$258

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

Summerland Key house

5 bedrooms / 5 bathrooms / sleeps 10

Price per night from

$873

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$231

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$298

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$329

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$244

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$130

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

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$161

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$210

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$430

New Listing!!! BIRDS OF PARADISE - Amazing Sunsets, Open Water Views, Dockage &

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$179

Isle Be Back!

Summerland Key house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$268

Sailfish Manor

Summerland Key house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$297

New Listing! KIKI'S CASA - Beautiful Canal Front Home W/ Pool & Dockage. Bring Y

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 9

Price per night from

$179

The Pointe

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$198

BLUE FISH POINT - Luxurious & Secluded Waterfront Oasis With Amazing Sunsets, Do

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$174

THE BLUE PEARL - Huge Open Water Home, Amazing Sunsets, Boat Bar & Room For The

Summerland Key house

4 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$174

Keys Life

Summerland Key house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$198

THE HIDEAWAY - Find It and Get Lost! Newly Decorated Canal Front Home w/ Dockage

Summerland Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$144

Great rentals within 20 miles that match your search

Cameron's Luxury Waterfront Estate with Dockage

Key West house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$589

Price per night from

$2,983

80' luxury yacht

Stock Island house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$4,001

PARADISE IN YOUR HANDS

Big Pine Key house

2 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 2 hours 12 minutes

Price per night from

$186

Charming 3bedroom/2bath home in the Florida Keys

Cudjoe Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

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

Ramrod Key house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$131

Island Time (both halves of duplex)

Big Pine Key house

5 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$228

Pirate's Cove

Cudjoe Key house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$93

Island Time 2 (half of duplex)

Big Pine Key house

3 bedrooms / 1 bathroom / sleeps 6

Price per night from

$123

Lafitte Landing

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$114

5 O'Clock Somewhere

Cudjoe Key house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$118

Island Chalet

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$138

Conch Out

Little Torch Key house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

Viewing 38 of 124
rentals in Summerland Key

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