Gulf Blue Vacations - Vacation Rentals in Key West

Amsterdam's Curry Mansion Inn From US $563
         

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8.8 (139 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pet Friendly
Luxury 3-Bedroom Waterfront Home with Pool AND Dock! From US $1,412
         

9.8 (132 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly

Luxury Places to Stay in Key West

Over 4762+ Luxury Places to Stay in or Near Key West
2 Sunset Harbor Resort Key West Florida
New
From US $11,498
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
2 Sunset Harbor Resort Key West Florida
New
From US $11,498
         

New
Resort
  • Air Conditioner
  • Pool
  • Balcony/Terrace
Lighthouse Suites Collection
New
From US $7,190
         

New
House
  • Air Conditioner
  • Parking
  • Pool
6 Bedroom 6 Bath Guesthouse on Duval Street From US $6,002
         

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9.5 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool

Top-Rated Vacation Rentals with a Pool in Key West

Over 3479+ Top-Rated Vacation Rentals with a Pool in or Near Key West
Almond Tree Inn Hotel - Adults Only From US $272
         

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10.0 (1003 Reviews)
Hotel
  • Air Conditioner
  • Parking
  • Pool

Pet-Friendly Vacation Rentals in Key West

Over 1506+ Pet-Friendly Vacation Rentals in or Near Key West
Green Mermaid From US $238
         

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New
House
  • Air Conditioner
  • Pet Friendly
  • Child Friendly
Capmar House by Brightwild Huge Home Pool From US $1,724
         

10.0 (1 Review)
House
  • Parking
  • Pet Friendly
  • Balcony/Terrace
See More Pet-Friendly Vacation Rentals in Key West on PetFriendly.io

Large Vacation Homes & Villas in Key West

Over 539+ Large Vacation Homes & Villas in or Near Key West
The Crestwood House - Private Heated Pool & Parking From US $2,969
         

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10.0 (2 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
3-Story spacious conch style home w/private pool & dock! From US $1,669
         

ARCHIPELAGO in the Truman Annex From US $798
         

9.4 (29 Reviews)
House
  • Parking
  • Pool
  • Balcony/Terrace

Wheelchair Accessible Vacation Homes in Key West

Over 1117+ Wheelchair Accessible Vacation Homes in or Near Key West
Point Break Suites From US $225
         

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7.3 (3 Reviews)
House
  • Air Conditioner
  • Parking
  • Pool
Weatherstation Inn From US $246
         

9.4 (992 Reviews)
Bed & Breakfast
  • Air Conditioner
  • Parking
  • Pool

Key West Varoom and Airbnb Places to Stay Under $200

Over 247+ Key West Varoom and Airbnb Places to Stay Under $200
Artist House Key West From US $200
         

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9.8 (417 Reviews)
Bed & Breakfast
  • Air Conditioner
  • TV
  • View
@ KEY WEST DOWNTOWN STUDIO APT AMAZING PRICES FOR WINTER OF 2025 From US $122
         

Sailor's Sanctuary - A Renovated Condo in Old Town From US $181
         

10.0 (11 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

Instantly Bookable Vacation Homes in Key West

Over 3055+ Instantly Bookable Vacation Homes in or Near Key West
Parking, Heated Pool, Pet Friendly - Seagate House From US $1,797
         

10.0 (13 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
BLUE HEAVEN at The Truman Annex in Key West From US $513
         

9.0 (50 Reviews)
Condo
  • Air Conditioner
  • Parking
  • Pool

About Key West Vacation Rentals

With more than 4771 Key West vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Gulfbluevacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Key West.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Gulfbluevacations Key West, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Key West. Places to stay near Key West are 765.05 ft² on average, with prices averaging $800 a night.

Gulfbluevacations makes it easy and safe to find and compare vacation rentals in Key West with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Key West

Type Count
Vacation Homes 2382
Holiday Apartments 590
Hotels with Suites 367
Resorts 232
Cottages 116
B&B 45
Villas 45
Cabin Rentals 7
Hostels 2
Others 1

Use these Quick Filters to Find a Vacation Rental in Key West

Pro Tip: Gulfbluevacations makes it easy to compare the best listings on Gulfbluevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Gulfbluevacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Key West.

Weather in Key West

View the weather forecast for Key West before booking your Key West Vacation Rentals to confirm your best time to go.

December - February
High 81°F       Low 67°F
March - May
High 87°F       Low 70°F
June - August
High 91°F       Low 80°F
September - November
High 90°F       Low 73°F