Vacation Rentals & House Rentals in Key West

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145 house rentals

Key Largo Bliss: Sun, Splash, Pickleball!

Key Largo house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Children's pool Jacuzzi or hot tub

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Price per night from

$567

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BEAUTIFUL YATCH IN THE KEYS ONCE IN A LIFETIME EXPERIENCE

Tavernier boathouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$252

Paradise at Moon Bay!

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$229

Anglers Reef Islamorada Florida Sleeps 6

Islamorada house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$344

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

Islamorada condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$158

Tropical Island Getaway-Keys

Key Largo condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$337

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

Key Largo apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Jacuzzi or hot tub, Children's pool

1 of 2 filters match

Price per night from

$315

Bahia Azul

Ramrod Key house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$268

One-bedroom time share suite in the heart of Old Key West

Key West condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 26 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$338

Hawkins Heaven

Cudjoe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$177

Islamorada Waterfront Paradise | 5br | Dock | Pool

Tavernier house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 12

Responds fast! avg. 3 hours 58 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$344

Breezy Palms

Marathon house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$659

The Caribbean Resort - Hemingway House North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Princess Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$458

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$115

Big Pine Bungalow: Serene Backyard Oasis, Pool/Spa, Expansive Canal-Facing Deck

Big Pine Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Pool, Hot Tub, D

Sugarloaf Key house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

Responds fast! avg. 2 hours 34 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$179

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Malayan Palm East

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$401

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Harbor House

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$859

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 43 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$630

Ocean Vista

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$201

Nature's Boutique

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 56 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$229

"Little Paradise" Historic Seaport Old Town Key West

Key West house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$492

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

Paradise on the water

Key Largo house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$573

Beautifully Designed Oceanfront Condo

Tavernier apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$464

SEAPORT SAILING—Beach-Pool-BBQ-55”TV-HotTub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$974

Hammerhead Hideaway- 2 Bed 2Bath Canal Front Home w/Cabana Club!

Key Colony Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$343

Sunrise at Seaside Condo 2 Bedroom

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Key West Adventure” We were two couples on our first visit to explore the keys. The condo was nice for four people. Not fancy but adequate. Could use a little updating to make it nicer. Located quite aways from Duval atreet and the action. Uber costs about $20 one way to get downtown. Too far to walk. The pool was amazing. No complaints.

Responds fast! avg. 2 hours 41 minutes

1 of 2 match: Children's pool, Jacuzzi or hot tub

1 of 2 filters match

Price per night from

$321

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