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.

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

Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool

Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

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

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

Island pool home awaits in Islamorada's Port Antigua

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

Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

Turtle Nest Estate in Islamorada
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.