Updating...

Enter dates for more accurate prices

Summerland Key Rentals

Filter

Bedrooms

  • Any
  • 1+ Bedrooms
  • 2+ Bedrooms
  • 3+ Bedrooms
  • 4+ Bedrooms
  • 5+ Bedrooms
  • 6+ Bedrooms
  • 7+ Bedrooms
  • 8+ Bedrooms
  • 9+ Bedrooms
  • 10+ Bedrooms
  • 11+ Bedrooms
  • 12+ Bedrooms
  • 13+ Bedrooms
  • 14+ Bedrooms
  • 15+ Bedrooms

Price range

Per night

$10 - $500

Summerland Key Rentals

22 apartments

Direct Atlantic Ocean front private boat ramp dock

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$140

1 / 14

Paradise n Summerland Key Cove

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 10

$159

1 / 20

Lower Florida Keys: Private Open Water Estate

Summerland Key house

4 bedrooms / 4 bathrooms / Sleeps 10

$857

1 / 14

Spacious, canal front villa w/ private pool and hot tub - 3 dogs are welcome!

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$162

1 / 29

Oceanfront vacation property with a variety of amenities. Rents weekly

Summerland Key cottage

1 bedroom / 1 bathroom / Sleeps 4

$140

1 / 4

Dolphin Beach

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$233

1 / 13

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$207

1 / 13

"THE PELICAN P00P" POOL, waterfront, A Really Cool Florida Keys Vacation Rental

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$150

1 / 14

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$168

1 / 18

Caribbean House

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$83

1 / 12

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$267

1 / 24

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

Summerland Key house

5 bedrooms / 5 bathrooms / Sleeps 10

$667

1 / 27

"Summerland Key Getaway"

Summerland Key house

4 bedrooms / 2 bathrooms / Sleeps 10

$400

1 / 24

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 18

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / Sleeps 8

$183

1 / 13

Island Living

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$150

1 / 15

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 14

Gulf Shores

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 13

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$200

1 / 12

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 8

$333

1 / 35

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / Sleeps 8

$200

1 / 22

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$142

1 / 17
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more