Search Islamorada villas with a pool

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 Windley Key Fossil Reef Geological State Park and ...
10/10 Exceptional! (6 reviews)
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Beautiful 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 ...
10/10 Exceptional! (1 review)
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Bayberry Key: Waterfront Htd Pool, FREE Boat Dockage Sep-Oct Only!
Angler’s Reef house. Paddle or Kayak to sandbar. Lic #24-0055

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

Stay at this villa in Islamorada. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Windley Key Fossil Reef Geological State Park and Rain ...
10/10 Exceptional! (12 reviews)
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Angler’s Reef house. Paddle or Kayak to sandbar. Lic #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 ...
10/10 Exceptional! (1 review)
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Isla 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 & ...
10/10 Exceptional! (2 reviews)
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Isla 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 villa in Islamorada. Enjoy free WiFi, private pools, and a water park. Popular attractions Sunset Drive Beach and Anne's ...
10/10 Exceptional! (6 reviews)
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Island pool home awaits in Islamorada's Port Antigua
Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl

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

Stay at this villa in Islamorada. Enjoy free WiFi, private pools, and laundry facilities. Popular attractions Matecumbe United Methodist Church and Keys History ...
10/10 Exceptional! (2 reviews)
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Villa with private plunge pool, boat dock, & amazing sunsets in Islamorada Fl
Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool

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

Stay at this villa in Islamorada. Enjoy private pools, laundry facilities, and air conditioning. Popular attractions Rain Barrel Village and Islamorada County ...
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Exclusive Private ViLLA , Beach, Boat Ramp, Dock, Pool
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 ...
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Isla 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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Turtle Nest Estate in Islamorada
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.