Book villas with a pool in Key West

Experience the Charm of Private Pool Villas in Key West

Booking a villa with a private pool in Key West provides an idyllic escape, perfect for families seeking both adventure and relaxation. These charming accommodations offer a unique blend of luxury, comfort, and privacy, allowing families to unwind after a day of exploring the vibrant island. With the sun shining and the gentle ocean breeze, you can enjoy quality time together by the pool, creating unforgettable memories. Key West's stunning beaches, lively culture, and beautiful sunsets are just a stone's throw away, making these villas an ideal choice for an unforgettable family getaway.

Our top choices for a great stay

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

Downtown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere

Stay at this villa in Key West. Enjoy private pools, laundry facilities, and patios. Our guests praise the property condition in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
9.8/10 Exceptional! (147 reviews)
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Opens in a new windowDowntown Duval Street Penthouse- Private Pool-Parking-Roof Deck- Walk Everywhere
Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

Location In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking

Stay at this villa in Key West. Enjoy private pools, laundry facilities, and tennis courts. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
9.8/10 Exceptional! (65 reviews)
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Opens in a new windowLocation In Down Town Key West W/ 2 Pools, Huge Private Roof Deck & Parking
Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool

Coral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool

Stay at this villa in Key West. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Duval Street and Smathers Beach are located nearby.
9.6/10 Exceptional! (13 reviews)
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Opens in a new windowCoral Palm by AvantStay | Key West Walkable| Gated Community & Shared Pool
Two Bedroom Two Bath Balcony Villa Steps from Duval!

Two Bedroom Two Bath Balcony Villa Steps from Duval!

$452 nightly
The price is $502 total per night from Oct 6 to Oct 7
$502 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this villa in Key West. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
10/10 Exceptional! (41 reviews)
Opens in a new windowTwo Bedroom Two Bath Balcony Villa Steps from Duval!
HYATT KEY WEST SUNSET HARBOR! Rarely Avail 2BR/2Bth - Best Location! 8/18-8/22

HYATT KEY WEST SUNSET HARBOR! Rarely Avail 2BR/2Bth - Best Location! 8/18-8/22

Stay at this villa in Key West. Enjoy laundry facilities, balconies, and air conditioning. Popular attractions Duval Street and Mallory Square are located nearby.
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Opens in a new windowHYATT KEY WEST SUNSET HARBOR! Rarely Avail 2BR/2Bth - Best Location! 8/18-8/22
Stunning 2-Bedroom Villa in Key West - Desirable Location - Hyatt Beach House!

Stunning 2-Bedroom Villa in Key West - Desirable Location - Hyatt Beach House!

Stay at this villa in Key West. Enjoy laundry facilities, air conditioning, and a hot tub. Popular attractions Duval Street and Smathers Beach are located nearby.
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Opens in a new windowStunning 2-Bedroom Villa in Key West - Desirable Location - Hyatt Beach House!
Poolside Queen Room Steps from Duval!

Poolside Queen Room Steps from Duval!

$202 nightly
The price is $224 total per night from Oct 6 to Oct 7
$224 total
Oct 6 - Oct 7
Total with taxes and fees
Stay at this villa in Key West. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
Opens in a new windowPoolside Queen Room Steps from Duval!
Secret Villa II @ Old Town: with Private Pool, close to Duval!

Secret Villa II @ Old Town: with Private Pool, close to Duval!

Book a stay at this family-friendly villa in Key West. Enjoy private pools, a water park, and a garden. Our guests praise the pool and the helpful staff in our reviews. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
10/10 Exceptional! (145 reviews)
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Opens in a new windowSecret Villa II @ Old Town: with Private Pool, close to Duval!
Two Bedroom Two Bath Poolside Villa Steps from Duval!

Two Bedroom Two Bath Poolside Villa Steps from Duval!

$570 nightly
The price is $632 total per night from Oct 12 to Oct 13
$632 total
Oct 12 - Oct 13
Total with taxes and fees
Stay at this villa in Key West. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Duval Street and Ernest Hemingway Home and Museum are located nearby.
10/10 Exceptional! (43 reviews)
Opens in a new windowTwo Bedroom Two Bath Poolside Villa Steps from Duval!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Why choose a villa with a pool in Key West instead of a hotel?

Opting for private villas with swimming pools in Key West provides a unique experience that hotels simply can’t match. For honeymooners, leisure seekers, or families, these luxury pool vacation villas for rent offer spacious living areas where you can create lasting memories together. With a private pool at your disposal, you can take refreshing dips whenever you desire, enjoying the tranquility without the crowds typically found at hotel pools. Villas also provide the flexibility to enjoy meals alfresco, host family gatherings, or indulge in peaceful moments under the stars. While hotels offer convenience and amenities, a villa allows you to tailor your experience, ensuring everyone has a memorable time in this tropical paradise. In Key West, the choice is clear for those seeking an exclusive retreat that combines comfort, joy, and the beauty of nature.