Holiday In The Hamptons - Vacation Rentals in Key West
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Luxury Places to Stay in Key West
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Top-Rated Vacation Rentals with a Pool in Key West
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Pet-Friendly Vacation Rentals in Key West
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Large Vacation Homes & Villas in Key West
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Wheelchair Accessible Vacation Homes in Key West
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Key West Vacation Rentals and Airbnb Places to Stay Under $200
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Instantly Bookable Vacation Homes in Key West
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About Key West Vacation Rentals
With more than 5015 Key West vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Holidayinthehamptons 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 Holidayinthehamptons 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 764.15 ft² on average, with prices averaging US $746 a night.
Holidayinthehamptons 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 | 2511 |
| Holiday Apartments | 610 |
| Hotels | 377 |
| Resorts | 242 |
| Cottages | 113 |
| B&B | 43 |
| Villas | 42 |
| Cabin Rentals | 7 |
| Others | 3 |
| Hostels | 2 |
Use these Quick Filters to Find a Vacation Rental in Key West
★ Pro Tip: Holidayinthehamptons makes it easy to compare the best listings on Holidayinthehamptons homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Holidayinthehamptons 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.
Top Attractions Around Key West, FL
Holidayinthehamptons offers a large selection of top attractions around Key West. Research things to do on your vacation before you visit Key West.
Other Places to Stay Near Key West, FL
Complexes around Key West, FL
Key West Vacation Rental Frequently Asked Questions
What are the top vacation rentals in Key West?
There are a lot of options in Key West. If you plan on staying in the Key West area, consider making a reservation for a few nights at one of these properties as these have been rated the Top Vacation Rentals in Key West:
- Almond Tree Inn Hotel - Adults Only
- Casa Cay West Beautiful Tropical 3 bedrooms 2 KING suites - 2 miles to beach
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Pineapple Cottage - Top-Rated Stay - Private Pool - 2BD/2.5Bath
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- Boli Townhouse - Luxury WEEKLY Rental in gated Truman Annex-Saturday to Saturday
- MAJESTIC PARADISE @ Truman Annex - Heart of Old Town, Key West
- Everything Key West has to offer @ Mango Cottage
- Secret Villa I @ Old Town with Private Pool, close to Duval!
- Key West Rooster
How many vacation rentals have private pools in Key West?
There are 851 vacation rentals with private pools near Key West. Top-rated homes that have access to a swimming pool include:
Which vacation homes in Key West are best for families?
If you are looking for a family-friendly vacation home in Key West, check out one of the following properties as all are highly-rated places to stay with excellent review for families or groups staying in Key West:
How many vacation rentals are available in Key West?
Currently, the total number of properties listed in 2026 is over 5015 in the Key West area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Key West.
