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

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Price per night from

$556

Hogfish Hideout

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$378

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

Summerland Key house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$764

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

$1,718

salty slumber get away

Summerland Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$395

Into the Mystic

Summerland Key house

  • 6 bedrooms
  • 6 bathrooms
  • sleeps 12

Match: Garden

All filters match

Price per night from

$465

Reel Paradise

Summerland Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$285

Great rentals within 20 miles that match your search

Family Retreat-Ocean front home with private pool

Cudjoe Key house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 14

Match: Garden

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Price per night from

$790

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

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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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

$801

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

$773

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

$573

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

$307

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

$573

Florida Keys at it's best

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$241

Match: Garden

All filters match

Price per night from

$210

Lower Keys Retreat.....

Big Pine Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

All filters match

Price per night from

$252

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

$384

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

$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

$258

Match: Garden

All filters match

Price per night from

$332

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

$800

Beautiful quiet neighborhood. Sunsets! Huge Pool!

Sugarloaf Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 30 minutes

Match: Garden

All filters match

Price per night from

$320

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

$150

Palmetto Retreat

Big Pine Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Garden

All filters match

Price per night from

$143

Pirates Paradise

Cudjoe Key house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$433

Blackbeard's Bounty

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$233

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

$409

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

$401

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

$773

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

$516

Relaxing 2/2 Get Away in the Lower Keys!

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

All filters match

Price per night from

$328

Ocean View Estate with Private Pool 15 minutes from Key West

Cudjoe Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“This vacation home has everything you need.” This home has all the amenities you could possibly need inside and out. Very quiet and secure with a great covered porch where we spent much of our time (we had 7 in our group). Plenty of towels and miscellaneous supplies. It was very easy to book and communicate with the owners. They responded promptly to any questions.

Responds fast! avg. 59 minutes

Match: Garden

All filters match

Price per night from

$544

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

$228

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