Book villas with a pool in Islamorada

Experience a Dream Getaway with Private Pool Villas in Islamorada

Villas with a private pool in Islamorada offer the perfect blend of luxury and comfort for families seeking a memorable vacation. Nestled in the stunning Florida Keys, these villas provide an idyllic setting for relaxation and adventure. With lush landscapes and the calming sounds of the ocean, you can unwind by your own pool after a day of exploring the beautiful beaches and local attractions. Each villa is designed to create lasting family memories, making it an ideal choice for your next getaway.

Our top choices for a great stay

Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.

Beautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.

Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and patios. Popular attractions Hog Heaven and Windley Key Fossil Reef Geological State Park are located nearby.
10/10 Exceptional! (6 reviews)
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Opens in a new windowBeautiful Venetian Shores, Cozy home, Heated pool, Tiki, Boat Lift, Fish & Dive.
Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and a garden. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
9.8/10 Exceptional! (8 reviews)
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Opens in a new windowBayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Islamorada Coastal Key West style house. Close to sandbars. License # 24-0055

Islamorada Coastal Key West style house. Close to sandbars. License # 24-0055

Book a stay at this family-friendly vacation home in Islamorada. Enjoy free WiFi, laundry facilities, and patios. Popular attractions Hog Heaven and Windley Key Fossil Reef Geological State Park are located nearby.
10/10 Exceptional! (23 reviews)
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Opens in a new windowIslamorada Coastal Key West style house. Close to sandbars. License # 24-0055
Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Isla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
9.2/10 Wonderful! (5 reviews)
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Opens in a new windowIsla Guava: Boutique Resort, FREE Boat Dockage Sept-Oct Only!
Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, laundry facilities, and balconies. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
9.8/10 Exceptional! (8 reviews)
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Opens in a new windowIsla Lychee: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Island pool home awaits in Islamorada's Port Antigua

Island pool home awaits in Islamorada's Port Antigua

Book a stay at this family-friendly vacation home in Islamorada. Enjoy free WiFi, private pools, and a sauna. Popular attractions Sunset Drive Beach and Anne's Beach are located nearby.
10/10 Exceptional! (7 reviews)
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Opens in a new windowIsland pool home awaits in Islamorada's Port Antigua
Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Isla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
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Opens in a new windowIsla Mirabelle: Boutique Resort, FREE Boat Dockage Sep-Oct Only!
Turtle Nest Estate in Islamorada

Turtle Nest Estate in Islamorada

2 out of 5
Stay at this villa in Islamorada. Enjoy a full-service spa. Popular attractions Robbie’s of Islamorada and Sunset Drive Beach are located nearby.
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Opens in a new windowTurtle Nest Estate in Islamorada
Island Palm Estate in Islamorada

Island Palm Estate in Islamorada

2 out of 5
Stay at this villa in Islamorada. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
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Opens in a new windowIsland Palm Estate in Islamorada
Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only

Isla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Islamorada Brewery & Distillery and Keys History & Discovery Center are located nearby.
10/10 Exceptional! (2 reviews)
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Opens in a new windowIsla Kiwi: Waterfront Boutique Resort, FREE Boat Dockage Sept-Oct Only
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 Islamorada?

Opting for a luxury pool vacation villa for rent in Islamorada instead of a hotel offers a unique experience tailored to your needs. These private villas with swimming pools provide ample space for families and couples to relax and reconnect, free from the constraints of hotel schedules and shared amenities. You can enjoy private poolside fun at your leisure, whether it's a morning swim or an evening barbecue under the stars. The villas often feature outdoor spaces perfect for family gatherings or intimate evenings, allowing you to create lasting memories in a tranquil setting. While hotels may offer convenience, villas provide a personalized touch, making it easy to blend relaxation with adventure. With nearby beaches and activities, your villa serves as a peaceful home base after a day of exploration, offering the best of both worlds—comfort and adventure—all in one beautiful destination.