Vacation Rentals & House Rentals in Florida Keys

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268 house rentals

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Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Children's pool Swimming pool

All filters match

Price per night from

$344

Bay Front Beauty/ Summer Sea Must See!!!!

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Swimming pool

All filters match

Price per night from

$158

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children's pool Swimming pool

All filters match

Price per night from

$568

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Children's pool Swimming pool

All filters match

Price per night from

$230

Sunset Water Views! Moon Bay Key Largo Remodeled Condo with Boat Slip!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Swimming pool

All filters match

Price per night from

$316

BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Swimming pool

All filters match

Price per night from

$253

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Children's pool Swimming pool

All filters match

Price per night from

$337

These homes match some but not all of your filters. Clear all filters

Executive Bay Club- great unit, great location!,

Islamorada villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 20 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$205

Lovely 2 bedroom, 2 bath condo at La Brisa.

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$161

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$376

Kawama Tower Unit 512

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$337

Key West, Private Beach, Fishing Pier, Old Town, Galleon Resort

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$490

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$166

Luxurious Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$297

Blackbeard's Escape

Little Torch Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$357

Reel Paradise Islamorada

Lower Matecumbe Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$212

Luxury 4-Bedroom Home with Resort Privileges

Tavernier villa

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$1,656

Beautiful condo with ocean view(distant)

Tavernier condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$257

The Mermaid House

Key Largo house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 2 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$341

Tranquil Oceanview Penthouse Paradise

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$371

Sunshine suit (2/2 apartment)

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$524

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$820

Island Suite @ KW Vacation

Key West apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$401

Comfy Family Home in a Gorgeous Gated Community

Key West townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$343

Bungalows at Sugarloaf Beach - The Lighthouse

Sugarloaf Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$1,141

Thirty Three by The Sea - Vacation Rental Key Colony Beach, FL

Key Colony Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$344

ISLAMORADA 3bd in WATERFRONT COMMUNITY w BEACH!!

Islamorada apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$364

2 BDR ISLAMORADA HOME in WATERFRONT - FREE DOCK!!

Islamorada studio

  • Studio
  • 2 bathrooms
  • sleeps 2

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$286

Alligator Reef Lighthouse Suite Duval St. and Pool

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$688

Tortugas Harbor Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$430

Key West Lighthouse Suite Duval St. and Pool

Key West cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$401

Sombrero Reef Lighthouse Suite Duval St. and Pool

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 30 minutes

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$430

A Change in Latitudes - TRUMAN ANNEX

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$172

Unit 10, Furnished Studio located 50 yards from ocean

Grassy Key apartment

  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$252

ISLAND DREAM

Lower Matecumbe Key house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$771

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

Little Torch Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$306

Key West Gulf front Home with private dock and pool.

Key West house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$480

Yellow vacation home, water view, boat dock, heated private pool.

Cudjoe Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Swimming pool

1 of 2 filters match

Price per night from

$474

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