Summerland Key Vacation Home Rentals, Treehouses & more


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Travelers going to Summerland Key are booking December dates now. Secure your vacation rental today and have the perfect trip.

Great rentals within 20 miles that match your search

1 / 14

House Key West

  • 4
  • 10
  • 30 nights min

$233

Details

1 / 20

Key Z Cottage Romantic Getaway

  • 2
  • 6
  • 3 nights min

$238

Details

1 / 15

Coral Hammock - Comfortable 3 Bedroom Home

  • 3
  • 6
  • 3 nights min

$250

Details

1 / 16

Beautiful Townhome at the entrance to Key West

  • 2
  • 5
  • Min stay varies

$201

Details

1 / 16

Sparkling canalfront house surrounded by palms

  • 2
  • 4
  • 30 nights min

$108

Details

1 / 24

Coral Hammock 34- 3 Bedroom Townhouse with a Shared Pool

  • 3
  • 6
  • Min stay varies

$300

Details

1 / 33

"Not Big Enough"

  • 3
  • 8
  • Min stay varies

$396

Details

1 / 29

Island Days: Parking and Pool - Fishing, Boating, Golfing, Dining, Shopping!

  • 3
  • 7
  • Min stay varies

$450

Details

1 / 17

Reel Paradise - Big Pine Key

  • 3
  • 6
  • Min stay varies

$134

Details

1 / 14

Tree House

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 20

Fisherman's Paradise in the Heart of Big Pine Key

  • 3
  • 6
  • 30 nights min

$99

Details

1 / 8

Blue Marlin

  • 3
  • 6
  • 30 nights min

$125

Details

1 / 25

Tropical Paradise Oceanfront Home with Pool

  • 2
  • 6
  • 7 nights min

$296

Details

1 / 16

Tropical Bay

  • 3
  • 5
  • 30 nights min

$83

Details

1 / 12

Blue Lagoon

  • 3
  • 6
  • 30 nights min

$201

Details

1 / 19

Bahia Azul

  • 4
  • 8
  • 30 nights min

$231

Details

1 / 11

Magnificent Ocean view with 35' dock , Canal home in gated Venture Out Resort

  • 2
  • 6
  • 3 nights min

$150

Details

1 / 22

Caribbean Dream

  • 4
  • 8
  • 30 nights min

$201

Details

1 / 18

Big Torch Retreat

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 14

Direct Atlantic Ocean front private boat ramp dock

  • 2
  • 6
  • Min stay varies

$140

Details

1 / 35

Oceanfront House

  • 3
  • 8
  • 30 nights min

$334

Details

1 / 20

Paradise n Summerland Key Cove

  • 3
  • 10
  • 30 nights min

$119

Details

1 / 15

Summerland Place

  • 3
  • 6
  • 30 nights min

$118

Details

1 / 12

Caribbean House

  • 2
  • 4
  • 30 nights min

$83

Details

1 / 13

Casa Turquesa

  • 3
  • 6
  • 30 nights min

$207

Details

1 / 13

Family Friendly House In Paradise

  • 5
  • 8
  • 30 nights min

$183

Details

1 / 13

Gulf Shores

  • 3
  • 6
  • 30 nights min

$100

Details

1 / 14

Cove Isles

  • 2
  • 4
  • 30 nights min

$110

Details

1 / 12

Ocean Breeze

  • 3
  • 6
  • 30 nights min

$164

Details

1 / 13

Dolphin Beach

  • 3
  • 6
  • 30 nights min

$233

Details

1 / 18

Cruikshank

  • 3
  • 6
  • 30 nights min

$169

Details

1 / 24

Villa Cayo

  • 3
  • 6
  • 30 nights min

$268

Details

1 / 15

Island Living

  • 3
  • 8
  • 30 nights min

$150

Details

1 / 27

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

  • 5
  • 10
  • 30 nights min

$667

Details

1 / 18

MELODY KEY - PRIVATE ISLAND

  • 3
  • 8
  • 6 nights min

$1250

Details

1 / 20

Beautiful Oceanfront 4/2 Home With Heated Pool/Spa

  • 4
  • 8
  • 30 nights min

$233

Details

1 / 4

Oceanfront vacation property with a variety of amenities. Rents weekly

  • 1
  • 4
  • 7 nights min

$140

Details

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