Owner Direct Vacation
Rentals in Key West
The Best Owner Direct Vacation Rentals in Key West. Explore thousands of vacation home rentals, large cabins, and villas near Key West
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Explore the Best Key West Vacation Homes
Looking for the perfect place to stay in Key West? Discover a curated collection of vacation rentals offering comfort, convenience, and authentic Key West character. Whether you want a beachfront condo, a cozy family home, or a pet-friendly stay close to downtown, Owner Direct makes it easy to compare verified options for your next trip.
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Why Travelers Love Using
Owner Direct to
Find Key West Vacation Rentals
What makes our vacation homes stand out?
Verified Properties
Every vacation home shown on Owner Direct comes from trusted travel sources and verified hosts, so you can browse with confidence.
Value You Can Trust
Compare a range of properties and find fair, transparent pricing—no hidden fees.
Endless Variety
From oceanfront condos and coastal cottages to luxury villas and family homes, there's a rental to fit every traveler and budget.
More Places to Stay Near Key West
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Popular Neighborhoods for Key West Vacation Rentals
What are the best areas to stay in Key West
Discover the top neighborhoods in Key West and choose a place that suits your stay.
Monday Jan 19
Key West, Florida
Common Vacation Rental Amenities Typical Vacation Rental Amenities
What sort of amenities will be available at your stay?
Our Key West vacation rentals are designed for comfort and convenience, with everything you need for a relaxing stay.
Indoor Amenities
Fully equipped kitchens
Spacious living areas with streaming TVs
Complimentary Wi-Fi
Air conditioning and heating
In-unit washer and dryer
Plush bedding and comfortable furniture
Outdoor Amenities
Balconies or patios with coastal views
Private or shared pools
BBQ grills and outdoor dining areas
On-site parking
Easy access to beaches and attractions
More Vacation Rentals You May Like Near Key West
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How to Reserve Your Key West Vacation Rental
Booking Made Simple
Owner Direct helps travelers find verified vacation rentals from trusted sources. Once you select a property you love, you’ll be guided to our partner’s secure booking platform to complete your reservation.
SEARCH PROPERTIES
Use filters for location, amenities, and budget.
VIEW DETAILS
Check photos, reviews, and features for your top picks.
BOOK SECURELY
Confirm your stay safely through our trusted travel partners.
Key West Vacation Rental FAQs
1. 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
- Condo in Old Town Key West's Truman Annex - Pool, Bicycle, Free Parking and WiFi
- Casa Capri Beautiful Tropical with 3 King Suites - 2 miles to beach
- Bright & Modern Condo—7 MinWalk to the Beach! Pool, Bikes & 2 Furnished Porches!
- PINEAPPLE COTTAGE: 2BR/2BA-Pvt Pool -1/2 block to Duval- RealKeyWest
- ~ Chick-A-Pea Cottage ~ Enjoy Key West’s charisma, with a pool, and parking!
- Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 days get 20% discount
- LOST SHAKER OF SALT ~ 3 Bed, 2 Bath Pet Friendly with 40' Private Heated Pool
- Casa Cove Beautiful Tropical 3 KING SUITES Sleeps 8- 2 miles to beach
2. How many vacation rentals have private pools in Key West?
There are 845 vacation rentals with private pools near Key West. Top-rated homes that have access to a swimming pool include:
3. 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:
4. How many vacation rentals are available in Key West?
Currently, the total number of properties listed in 2026 is over 4802 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.