Vacation Rentals & House Rentals in Key West

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45 house rentals

Key West Beachfront Luxury 2/2 Condo A212 No Hurricane Damage

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect place to experience Key West” This is a lovely condo with a tropical, quiet view. Many extras are included: beach towels, bikes, and kitchen supplies. The pool area was our favorite spot, and we had coffee every morning on the balcony with chairs for all 6 of us. My husband enjoyed watching March Madness on the large T.V. Kathy did a fantastic job with all communications and provided great tourist tips. We would definitely stay here again!

Match: Waterfront

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Price per night from

$659

Oceanfront 2 Bedroom 2 Bath Condo Key West Florida

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Perfect location and great value!” From the moment we arrived, this condo was everything we wanted without breaking the bank. We spent days looking for a place in Key West for Christmas week. What was available was crazy expensive, so to be honest when we found this place for the price we were slightly apprehensive. It is close to everything, the check-in and check-out were easy, the people who live in the complex were very friendly and welcoming and always willing to offer advice on where to go and what to do. Everything worked and was clean and we could not have asked for a better vacation. Can't wait to go back!

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Price per night from

$434

NEW LISTING! 40’ Luxury Catamaran Yacht!

Key West yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

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Price per night from

$1,946

Atlantic Paradise Found modern luxury Best pool in Key West fine finishes

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$1,374

KEY WEST and 3 Bikes or Walk Everywhere! 2 Porches, Pool, Parking & WIFI

Key West condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Waterfront

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Price per night from

$342

Henry's Piece Of Paradise On The Ocean In Key West

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“nice place” Accommodations were nice Good view Henry was great to work with

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Price per night from

$464

Key West Affordable Ocean View Condo. Clean priced well on the Atlantic

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$745

Anchor Drop modern elegance upgrades throughout views of Atlantic Ocean

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$1,374

Amazingly Transformed in 2022 Luxurious renovation Fantastic Ocean View

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$974

Tropical Paradise Key West - Upgraded Master Bath - Best Value Discounts

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$859

Ocean Front Key West Oasis Island Tones Charming Historical Downtown area

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$764

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Price per night from

$911

Salty Sea Breezes, Exquisite Morning Sunrises, Luxurious Condo. Fall Specials

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$840

Key West Morning reflections, Balmy Ocean Breezes, Downtown family fun

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$382

SEAPORT SERENITY in Old Town—Beach-Pool-BBQ-Hot Tub

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$911

Atlantic Ocean Breezes, Tropical Island Sunrises, Downtown 10 minutes away

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$382

The Mermaids House, Historic Old Town Key West

Key West house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Beautiful Home in Old Town Key West” Mermaid House is conveniently located in the heart of Old Town yet when you are there you are in your own private paradise. The house is beautifully appointed with anything you could need during your stay and has ample space for four people. It was the perfect spot for our stay in Key West and we plan to stay again when we return to the area. Thanks to Barbara for making us feel welcome and for sharing her beautiful home with us.

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Price per night from

$328

Somewhere on the Beach a dream property all amenities included simply amazing

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,432

Key Wes't Best- Upgraded condo 5 mins to Smathers Beach Fantastic value

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$1,374

High Tide awaits your next visit upgraded condo close to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$859

Artist Cottage

Key West apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Key West, Spring 2012” In a word,our stay with you was ”wonderful”. We have been to Key West on several occasions and have loved every visit. Staying in Truman annexe was even more special. We all felt like we were at home with everything we needed. You must feel blessed to live in that part of the world. We will be looking for a job for our 19 year old son,Tom. He wants to come and work over in Key West. We have just arrived home and everything seems grey, and much colder than Key West. Depending on finances( the pound-dollar rate is not too good just now) we hope to come back soon. We will definitely be giving you a call.I would recommend your accommodation and company to future holiday makers. Love and blessings John,Jayne,Jack and Tom

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Price per night from

$379

Mar Y Sol a spectacular Ocean Front Oasis 10 minutes to Historic District

Key West apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$1,718

Frost Free at 1800 Atlantic overlooking Smathers Beach top floor & upgrades

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,145

Top floor Ocean Views, Spacious 2 Bedroom Condo, Views from every room

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$974

Paradise Found in Key West upgrades throughout 5 minutes to Smathers Beach

Key West apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$859

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

Key West condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$971

Noah, Family Ocean Paradise

Key West house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$1,330

Great rentals within 20 miles that match your search

80' luxury yacht

Stock Island house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$3,996

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

Stock Island house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 11

Match: Waterfront

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Price per night from

$797

Coconuts on the Water

Stock Island house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 38 minutes

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Price per night from

$205

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Price per night from

$262

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$523

Cassie's Paradise

Sugarloaf Key house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

Match: Waterfront

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Price per night from

$5,724

Walk to Duval and Mallory Square!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$623

Hyatt Beach House! Quiet Key West Location!

Stock Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$471

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Hyatt Windward Pointe

Stock Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$525

Bow Channel Manor

Sugarloaf house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Waterfront

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Price per night from

$257

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