The Best Private
Villas in Islamorada

Anglers Reef Paradise is located in Islamorada, 300 metres from Windley Key, and a private beach area, free bikes and an outdoor swimming pool are accessible in-house. This property offers free WiFi. This air-conditioned holiday home has 2 bedrooms and 2.5 bathrooms, a cable flat-screen TV, and a fully equipped kitchen. The holiday home also provides a bathroom with a shower. The holiday home includes a barbecue. There is a a terrace at this property and guests can go snorkelling, fishing and diving nearby. Two kayaks and 2 bicycles are offered. A boat hire is available for a surcharge. Theater of the Sea on Islamorada is 800 metres from Anglers Reef Paradise, while Upper Matecumbe Key is 5 km from the property. Show full description

Featuring air-conditioned accommodation with a pool with a view, garden view and a patio, Anglers Reef Getaway is set in Islamorada. This beachfront property offers access to a balcony, squash on the squash court, free private parking and free WiFi. The villa with a terrace and pool views features 2 bedrooms, 2 living rooms, a flat-screen TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the villa. The property is non-smoking and is situated 600 metres from Windley Key. The property has an outdoor dining area. Guests can take advantage of the warm weather with the property's barbecue facilities. Guests at the villa will be able to enjoy activities in and around Islamorada, like fishing. Snorkelling and cycling can be enjoyed nearby, while a bicycle rental service and a private beach area are also available on-site. Upper Matecumbe Key is 5.5 km from Anglers Reef Getaway, while Pigeon Key is 16 km away. The nearest airport is Miami International Airport, 115 km from the accommodation. Show full description

Situated in Islamorada and only 3.8 km from Windley Key, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with sea views, free WiFi and free private parking. This holiday home offers a private beach area, a garden, as well as a tennis court. The property features a year-round outdoor pool with a pool bar and is set 9.1 km from Upper Matecumbe Key. Some units in the holiday home have private entrance and are fitted with desk and wardrobe. Some of the units have a satellite flat-screen TV, a fully equipped kitchen with a dishwasher, and a private bathroom with a walk-in shower and a hair dryer. In some units there is a dressing room for guests to change in. A bar can be found on-site, and in the warmer months you can make use of the barbecue facilities. The holiday home has a picnic area and a terrace. Pigeon Key is 13 km from EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS, while John Pennekamp State Park is 26 km from the property. The nearest airport is Miami International Airport, 112 km from the accommodation. Show full description

Situated in Islamorada, just 80 metres from Sea Oats Beach, Paradise Beach features beachfront accommodation with a garden and free WiFi. The air-conditioned accommodation is 1.9 km from Anne's Beach. The property provides a children's playground, parking on-site and an electric vehicle charging station. The holiday home has 3 bedrooms, 3 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a patio with sea views. Guests can take in the ambience of the surroundings from an outdoor dining area. For added privacy, the accommodation features a private entrance. Guests at the holiday home will be able to enjoy activities in and around Islamorada, like cycling. Upper Matecumbe Key is 13 km from Paradise Beach, while Windley Key is 18 km from the property. The nearest airport is Key West International Airport, 115 km from the accommodation. Show full description

Set in Islamorada, a few steps from Sea Oats Beach and 1.6 km from Anne's Beach, Sun-kissed Bliss offers air-conditioned accommodation with a balcony and free WiFi. This holiday home features accommodation with a patio. The property is non-smoking and is situated 13 km from Upper Matecumbe Key. The spacious holiday home is fitted with 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, and 3 bathrooms with an a bath or shower, free toiletries and a washing machine. Towels and bed linen are offered in the holiday home. For added privacy, the accommodation features a private entrance. Windley Key is 18 km from the holiday home, while Pigeon Key is 34 km from the property. The nearest airport is Key West International Airport, 115 km from Sun-kissed Bliss. Show full description

Boasting air-conditioned accommodation with a private pool, sea view and a balcony, The Oasis is set in Islamorada. This beachfront property offers access to a terrace and free private parking. The accommodation offers free shuttle service, full-day security and currency exchange for guests. The spacious holiday home is located on the ground floor and is fitted with 3 bedrooms, a flat-screen TV with streaming services and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The unit is soundproofed and is comprised of a tiled floors as well as a fireplace. This holiday home is allergy-free and non-smoking. In the warmer months, you can make use of the barbecue facilities and dine on the private patio. The area is popular for canoeing, and free use of bicycles is available at the holiday home. Snorkelling and cycling can be enjoyed nearby, while a private beach area and water sports facilities are also available on-site. Upper Matecumbe Key is 1.6 km from The Oasis, while Windley Key is 4 km from the property. The nearest airport is Miami International Airport, 119 km from the accommodation. Show full description

Featuring air-conditioned accommodation with a patio, Casa Koto is located in Islamorada. This beachfront property offers access to a balcony and free WiFi. The property provides a children's playground and parking on-site. The spacious holiday home features 6 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 5 bathrooms with a walk-in shower. Towels and bed linen are provided in the holiday home. The property has an outdoor dining area. Guests at the holiday home will be able to enjoy activities in and around Islamorada, like cycling. Guests can also relax in the garden. Sea Oats Beach is 1.2 km from Casa Koto, while Anne's Beach is 2.3 km away. The nearest airport is Key West International Airport, 116 km from the accommodation. Show full description

Boasting air-conditioned accommodation with a private pool, pool view and a patio, Waterfront Wonder is set in Islamorada. The property is located 2.5 km from Anne's Beach, 12 km from Upper Matecumbe Key and 17 km from Windley Key. Free WiFi is available throughout the property and Sea Oats Beach is less than 1 km away. The spacious holiday home has 6 bedrooms, 6 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a balcony with sea views. Guests can take in the ambience of the surroundings from an outdoor dining area or keep themselves warm by the fireplace on colder days. For added privacy, the accommodation features a private entrance. For guests with children, the holiday home offers a children's playground. Pigeon Key is 33 km from Waterfront Wonder, while Florida Keys Aquarium Encounters is 36 km from the property. The nearest airport is Key West International Airport, 116 km from the accommodation. Show full description

Located in Islamorada, less than 1 km from Anne's Beach and a 17-minute walk from Sea Oats Beach, Two White Turtles provides air-conditioned accommodation with a patio and free WiFi. The property is set 19 km from Windley Key, 34 km from Florida Keys Aquarium Encounters and 35 km from Pigeon Key. The property is non-smoking and is situated 14 km from Upper Matecumbe Key. The holiday home features 2 bedrooms, a TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area. John Pennekamp State Park is 47 km from the holiday home, while History of Diving Museum is 15 km away. The nearest airport is Key West International Airport, 115 km from Two White Turtles. Show full description

Set in Islamorada, 1.2 km from Sea Oats Beach and 2.2 km from Anne's Beach, Plaza Del Sol offers air-conditioned accommodation with a terrace and free WiFi. This holiday home features accommodation with a balcony. The property is non-smoking and is situated 13 km from Upper Matecumbe Key. The spacious holiday home features 4 bedrooms, a TV, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area. Guests at the holiday home will be able to enjoy activities in and around Islamorada, like cycling. Windley Key is 18 km from Plaza Del Sol, while Pigeon Key is 34 km away. The nearest airport is Key West International Airport, 116 km from the accommodation. Show full description

Set in Islamorada, 1.1 km from Sea Oats Beach and 10 km from Upper Matecumbe Key, Beachfront Villa at Islamorada BY THE GLAMHOMES offers a private beach area and air conditioning. This beachfront property offers access to a balcony, free private parking and free WiFi. On clear days, guests can head outside to enjoy the villa's outdoor fireplace or simply kick back and relax. The spacious villa with a terrace and sea views features 4 bedrooms, a living room, a flat-screen TV, an equipped kitchen with an oven and a microwave, and 4 bathrooms with a bath. Towels and bed linen are featured in the villa. There is also a seating area and a fireplace. If you would like to discover the area, canoeing is possible in the surroundings and the villa can arrange a car rental service. Windley Key is 15 km from Beachfront Villa at Islamorada BY THE GLAMHOMES, while Pigeon Key is 31 km away. The nearest airport is Key West International Airport, 117 km from the accommodation. Show full description

Located in Islamorada, 2 km from Upper Matecumbe Key and 7 km from Windley Key, Islamorada Modern Penthouse with Private Beach offers a private beach area and air conditioning. This beachfront property offers access to a balcony, free private parking and free WiFi. The villa features an outdoor swimming pool with a fence, as well as a hot tub and a lift. The villa is equipped with 3 bedrooms, a flat-screen TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a fridge. Towels and bed linen are provided in the villa. The accommodation offers a fireplace. Guests can relax in the garden at the property. Pigeon Key is 23 km from the villa, while John Pennekamp State Park is 36 km away. The nearest airport is Miami International Airport, 122 km from Islamorada Modern Penthouse with Private Beach. Show full description

Newly opened, October 2023. Set in Islamorada, 500 metres from Anne's Beach and 1.7 km from Sea Oats Beach, Tollgate Tides offers air-conditioned accommodation with a patio and free WiFi. The property has garden views and is 13 km from Upper Matecumbe Key and 18 km from Windley Key. The property provides a children's playground and parking on-site. The spacious holiday home with a balcony and sea views features 2 bedrooms, a living room, a TV, an equipped kitchen with a dishwasher and an oven, and 2 bathrooms with a walk-in shower. Towels and bed linen are featured in the holiday home. The property has an outdoor dining area. Guests can also relax in the garden. Florida Keys Aquarium Encounters is 34 km from the holiday home, while Pigeon Key is 34 km away. The nearest airport is Key West International Airport, 114 km from Tollgate Tides. Show full description

Newly opened, November 2023. Featuring air-conditioned accommodation with a patio, 3 Lux Ensuites Walk Boat Island is located in Islamorada. The property is situated 5.5 km from Windley Key, 22 km from Pigeon Key and 34 km from John Pennekamp State Park. The property is non-smoking and is set 500 metres from Upper Matecumbe Key. With free WiFi, this 3-bedroom holiday home provides a cable TV, a washing machine and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance. Florida Keys Aquarium Encounters is 46 km from the holiday home, while History of Diving Museum is 2.3 km away. The nearest airport is Miami International Airport, 121 km from 3 Lux Ensuites Walk Boat Island. Show full description

Newly opened, November 2023. Featuring air-conditioned accommodation with a patio, Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK is located in Islamorada. The property is around 1.4 km from Anne's Beach, 12 km from Upper Matecumbe Key and 17 km from Windley Key. The property is non-smoking and is set 200 metres from Sea Oats Beach. With free WiFi, this 4-bedroom holiday home provides a cable TV, a washing machine and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are provided in the holiday home. For added privacy, the accommodation features a private entrance. Pigeon Key is 34 km from the holiday home, while Florida Keys Aquarium Encounters is 35 km away. The nearest airport is Key West International Airport, 115 km from Unity & Autonomy 2 sides a Beach Duplex & 70' DOCK. Show full description

Boasting air-conditioned accommodation with a private pool, garden view and a balcony, Anglers Reef Vacation Rental is set in Islamorada. Situated 500 metres from Windley Key, the property features a private beach area and free private parking. With free WiFi, this 2-bedroom villa offers a cable flat-screen TV, a washing machine and a fully equipped kitchen with kitchenware. Guests at the villa will be able to enjoy activities in and around Islamorada, like canoeing. The property is non-smoking and is located 5.5 km from Upper Matecumbe Key. Guests can take advantage of the warm weather with the property's barbecue facilities. Snorkelling, cycling and fishing are possible within the area, and Anglers Reef Vacation Rental offers water sports facilities. Pigeon Key is 16 km from the accommodation, while John Pennekamp State Park is 29 km from the property. The nearest airport is Miami International Airport, 115 km from Anglers Reef Vacation Rental. Show full description

Newly opened, December 2023. Situated in Islamorada, 1.4 km from Sea Oats Beach and 13 km from Upper Matecumbe Key, Gemstone Isle offers a garden and air conditioning. It is set 18 km from Windley Key and features an ATM. Free WiFi is available throughout the property and Anne's Beach is 600 metres away. The spacious holiday home features 2 bedrooms, 2 bathrooms, bed linen, towels, a TV with cable channels, a dining area, a fully equipped kitchen, and a patio with sea views. Guests can enjoy a meal on an outdoor dining area while overlooking the garden views. For added privacy, the accommodation features a private entrance. Guests at the holiday home will be able to enjoy activities in and around Islamorada, like cycling. Florida Keys Aquarium Encounters is 34 km from Gemstone Isle, while Pigeon Key is 34 km from the property. The nearest airport is Key West International Airport, 114 km from the accommodation. Show full description

Situated 2.3 km from Anne's Beach, 13 km from Upper Matecumbe Key and 18 km from Windley Key, Antigua Place provides accommodation set in Islamorada. Among the facilities at this property are a 24-hour front desk and an ATM, along with free WiFi throughout the property. The property is non-smoking and is located 1.4 km from Sea Oats Beach. Pigeon Key is 34 km from the holiday home, while Florida Keys Aquarium Encounters is 36 km away. The nearest airport is Key West International Airport, 116 km from Antigua Place. Show full description

Featuring sea views, Beacon Reef 222 offers accommodation with a garden and a terrace, around 2.4 km from Upper Matecumbe Key. Among the facilities at this property are a 24-hour front desk and a lift, along with free WiFi throughout the property. The holiday home features parking on-site, a fitness room and an ATM. The spacious holiday home is fitted with 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking. Windley Key is 3.1 km from the holiday home, while Pigeon Key is 19 km away. The nearest airport is Miami International Airport, 118 km from Beacon Reef 222. Show full description

Boasting sea views, Beacon Reef 301 features accommodation with a garden and a terrace, around 2.4 km from Upper Matecumbe Key. Among the facilities at this property are a 24-hour front desk and a lift, along with free WiFi throughout the property. The holiday home also offers facilities for disabled guests. The holiday home features 2 bedrooms, a TV with cable channels and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. The accommodation is non-smoking. Windley Key is 3.1 km from the holiday home, while Pigeon Key is 19 km from the property. The nearest airport is Miami International Airport, 118 km from Beacon Reef 301. Show full description