Summerland Key Rentals

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40 Houses

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

Summerland Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$557

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$379

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

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$766

Acreage Multi-Million Dollar Beachfront Mansion w/ Pool & Billiards

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$1,722

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$396

Into the Mystic

Summerland Key house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$466

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$286

Great rentals within 20 miles that match your search

New Listing! Beautiful Canal front , Key Deer and jacuzzi.

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$287

Waterfront Beach House with Dock and Heated Pool!

Little Torch Key house

  • 8 bedrooms
  • 5 bathrooms
  • sleeps 20

Match: Garden

All filters match

Price per night from

$803

Hogfish Retreat

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$178

Conch House - Dock Your Boat

Little Torch Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 7

Match: Garden

All filters match

Price per night from

$775

Blue Palms Retreat. ocean front w/pool and dock for your boat.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$574

5 Pirate's Hideaway Canal Front Home with Seawall & Kayaks

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

Match: Garden

All filters match

Price per night from

$308

Match: Garden

All filters match

Price per night from

$210

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$241

$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

Match: Garden

All filters match

Price per night from

$259

Charming House on deep clear canal

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 2 hours 44 minutes

Match: Garden

All filters match

Price per night from

$201

Tranquility in Paradise - Cudjoe

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$218

Tranquility in Paradise - Sugarloaf

Sugarloaf Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$385

Oceanside, pet friendly, smart home with plenty of paddle equipment

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$224

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$253

Upscale ocean front home & easy canal boat access to Gulf or Atlantic ocean

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$240

Agua Azul

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$151

Match: Garden

All filters match

Price per night from

$333

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Match: Garden

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Price per night from

$321

Entire House with Deep Water Dock & Heated Pool - 4 Min. to KW - Pets OK

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Garden

All filters match

Price per night from

$801

Palmetto Retreat

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$144

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$434

Blackbeard's Bounty

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$234

Private House Facing the Ocean with Heated Pool/Spa

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$410

Boaters Dream House in the Water with 175’ of Sea Wall

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$775

Lower Keys PARADISE 200 Ft of Dockage, Heated Pool, Quick Atlantic Access

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 24 minutes

Match: Garden

All filters match

Price per night from

$402

Island Time on Cudjoe Key! 20 miles from Key West. Quick open water access.

Cudjoe Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$517

Big Pine Key/Hot tub/Canal Home/updated

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 7

Match: Garden

All filters match

Price per night from

$229

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Garden

All filters match

Price per night from

$792

Starfish House - Dock your boat at your front door

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$574

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Garden

All filters match

Price per night from

$5,733

Sharkys Island Paradise

Big Pine Key house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$259

Viewing 38 of 40
rentals in Summerland Key

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