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

147 apartments

Oceanfront House

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 8

Responds fast! avg. 3 hours 43 minutes

$333

1 / 50

Island Living

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 8

$163

1 / 15

Paradise n Summerland Key Cove

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 10

$159

1 / 20

Oceanfront vacation property with a variety of amenities. Rents weekly

Summerland Key cottage

1 bedroom / 1 bathroom / Sleeps 4

$140

1 / 4

"Summerland Key Getaway"

Summerland Key house

4 bedrooms / 2 bathrooms / Sleeps 10

$400

1 / 24

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

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

Responds fast! avg. 20 minutes

$152

1 / 29

Living in Paradise

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$99

1 / 19

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

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 9

$150

1 / 18

Blue Lagoon

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$200

1 / 12

Caribbean Dream

Summerland Key house

4 bedrooms / 3 bathrooms / Sleeps 8

$200

1 / 22

Direct Atlantic Ocean front private boat ramp dock

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 6

$140

1 / 14

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

Summerland Key house

5 bedrooms / 5 bathrooms / Sleeps 10

$668

1 / 27

Family Friendly House In Paradise

Summerland Key house

5 bedrooms / 3 bathrooms / Sleeps 8

$184

1 / 13

Villa Cayo

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$267

1 / 24

Caribbean House

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$83

1 / 12

Casa Turquesa

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$208

1 / 13

Big Torch Retreat

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 18

Cruikshank

Summerland Key house

3 bedrooms / 3 bathrooms / Sleeps 6

$168

1 / 18

Gulf Shores

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$100

1 / 13

Cove Isles

Summerland Key house

2 bedrooms / 2 bathrooms / Sleeps 4

$110

1 / 14

Paradise Palms

Summerland Key house

3 bedrooms / 2 bathrooms / Sleeps 6

$143

1 / 17
Viewing 38 of 147
Payment Protection
Your payment for this rental is protected when you pay through FlipKey. Learn more