The Best Private
Villas in Islamorada

Situated in Islamorada in the Florida region and Windley Key reachable within 500 metres, Anglers Reef Paradise features accommodation with free WiFi, barbecue facilities, a private beach area and free private parking. Guests can benefit from a balcony and a year-round outdoor pool. The property is non-smoking and is set 1.2 km from Theater Of The Sea On Islamorada. Boasting a DVD player, the spacious holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room, a dining area, 2 bedrooms, and 2 bathrooms with a walk-in shower. The unit is air conditioned and is comprised of a terrace with outdoor furniture as well as a flat-screen TV with streaming services. 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 fishing. If you would like to discover the area, snorkelling, diving and cycling are possible in the surroundings and Anglers Reef Paradise can arrange a bicycle rental service. Upper Matecumbe Key is 5.5 km from the accommodation, while Pigeon Key is 16 km from the property. Miami International Airport is 115 km away. Show full description

Opened May 2024. Boasting air-conditioned accommodation with a balcony, Bayberry Key - Waterfront Boutique Resort, Dock, Direct Water views! is set in Islamorada. Featuring a 24-hour front desk, this property also provides guests with a year-round outdoor pool. Offering free WiFi throughout the property, the non-smoking holiday home has a spa centre. The holiday home is fitted with 3 bedrooms, a TV and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. Guests can relax in the garden at the property. Upper Matecumbe Key is 1 km from the holiday home, while Theater Of The Sea On Islamorada is 3.4 km from the property. Miami International Airport is 119 km away. Show full description

Boasting a balcony with garden views, a private beach area and water sports facilities, Anglers Reef Vacation Rental can be found in Islamorada, close to Windley Key and 1.2 km from Theater Of The Sea On Islamorada. This villa has a private pool, barbecue facilities and free private parking. The property is non-smoking and is set 5.5 km from Upper Matecumbe Key. 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 snorkelling, cycling and fishing. If you would like to discover the area, canoeing is possible in the surroundings. Pigeon Key is 16 km from Anglers Reef Vacation Rental, while John Pennekamp State Park is 29 km from the property. Miami International Airport is 115 km away. Show full description

Located only 8.5 km from Upper Matecumbe Key in Islamorada, Key Lime Cottage in the heart of Islamorada provides accommodation equipped with a patio, garden and year-round outdoor pool. The air-conditioned accommodation is 2.6 km from Sea Oats Beach, and guests can benefit from private parking available on site and free WiFi. The property is non-smoking and is set 13 km from Theater Of The Sea On Islamorada. The holiday home comes with 2 bedrooms, 1 bathroom, bed linen, towels, a flat-screen TV with streaming services, a fully equipped kitchen, and a terrace with garden views. For added privacy, the accommodation features a private entrance. Outdoor play equipment is also available for guests at the holiday home. Windley Key is 14 km from Key Lime Cottage in the heart of Islamorada, while Pigeon Key is 30 km away. Key West International Airport is 119 km from the property. Show full description

Facing the seafront in Islamorada, Islamorada Modern Penthouse with Private Beach is a holiday home, featuring an outdoor pool and parking on-site. This holiday home provides air-conditioned accommodation with a balcony. Providing free WiFi throughout the property, the non-smoking holiday home has a hot tub. The spacious holiday home features 3 bedrooms, a flat-screen TV with cable channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a hot tub. Towels and bed linen are provided in the holiday home. The accommodation offers a fireplace. Guests can relax in the garden at the property. Upper Matecumbe Key is 2 km from the holiday home, while Theater Of The Sea On Islamorada is 6.1 km away. Miami International Airport is 122 km from the property. Show full description

Situated in Islamorada in the Florida region and Windley Key reachable within 3.8 km, EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS features accommodation with free WiFi, barbecue facilities, a private beach area and free private parking. The air-conditioned accommodation is 9.1 km from Upper Matecumbe Key. The property features a year-round outdoor pool with a pool bar and is set 4.8 km from Theater Of The Sea On Islamorada. The holiday home provides guests with a terrace, a seating area, satellite flat-screen TV, a fully equipped kitchen with a dishwasher and an oven, and a private bathroom with walk-in shower and a hair dryer. Some units have a balcony and/or a patio with sea or garden views. At the holiday home, every unit is equipped with bed linen and towels. Guests are welcome to unwind in the in-house bar or lounge. You can play tennis at the holiday home. The holiday home has a picnic area where you can spend a day out in the open. Pigeon Key is 13 km from EXECUTIVE BAY ISLAMORADA BY SOFLA VACATIONS, while John Pennekamp State Park is 26 km from the property. Miami International Airport is 112 km away. Show full description

Paradise Beach is a beachfront property situated in Islamorada, a few steps from Sea Oats Beach and 13 km from Upper Matecumbe Key. The air-conditioned accommodation is 17 km from Theater Of The Sea On Islamorada. The property has a restaurant with an outdoor dining area. The holiday home has 3 bedrooms, 3 bathrooms, bed linen, towels, a TV with streaming services, a dining area, a fully equipped kitchen, and a patio with sea 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. Paradise Beach features a children's playground and a picnic area. Windley Key is 18 km from the accommodation, while Pigeon Key is 34 km from the property. Key West International Airport is 115 km away. Show full description

Boasting a balcony with sea views, a private beach area and water sports facilities, The Oasis can be found in Islamorada, close to Upper Matecumbe Key and 3.1 km from Theater Of The Sea On 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. Featuring air conditioning, this unit has a dressing room and a fireplace. This holiday home is allergy-free and non-smoking. The area is popular for canoeing, and free use of bicycles is available at the holiday home. Guests can swim in the pool with a view, go snorkelling or cycling, or relax in the garden and use the barbecue facilities. Windley Key is 4 km from The Oasis, while Pigeon Key is 20 km from the property. Miami International Airport is 119 km away. Show full description

Boasting air-conditioned accommodation with a private pool, pool view and a balcony, Waterfront Wonder is set in Islamorada. Guests can benefit from a patio and a children's playground. The property has a lift, a restaurant with an outdoor dining area. The spacious holiday home has 6 bedrooms, 5 bathrooms, bed linen, towels, a TV with streaming services, a dining area, a fully equipped kitchen, and a terrace with sea views. There is also a seating area and a fireplace. The holiday home has a picnic area where you can spend a day out in the open. Sea Oats Beach is less than 1 km from the holiday home, while Upper Matecumbe Key is 12 km from the property. Key West International Airport is 116 km away. Show full description

Located in Islamorada, just 1.4 km from Sea Oats Beach, Turtle Nest Estate provides beachfront accommodation with a private beach area, an outdoor swimming pool, an open-air bath and free WiFi. The property is situated 10 km from Upper Matecumbe Key, 14 km from Theater Of The Sea On Islamorada and 15 km from Windley Key. The villa features a hot tub and a lift. The air-conditioned villa is composed of 4 separate bedrooms, a fully equipped kitchen with a dishwasher and a microwave, and 4 bathrooms. The accommodation is non-smoking. Pigeon Key is 31 km from the villa, while Florida Keys Aquarium Encounters is 37 km away. A flat-screen TV is provided. Key West International Airport is 117 km from the property. Show full description

Opened October 2023. Featuring air-conditioned accommodation with a balcony, Tollgate Tides is set in Islamorada. With garden views, this accommodation offers a patio. The property has a restaurant with an outdoor dining area. The spacious holiday home with a terrace 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. For added privacy, the accommodation features a private entrance. A children's playground is also available for guests at the holiday home. Anne's Beach is 500 metres from Tollgate Tides, while Upper Matecumbe Key is 13 km away. Key West International Airport is 114 km from the property. Show full description

Antigua Place is located in Islamorada, 1.5 km from Sea Oats Beach, 13 km from Upper Matecumbe Key, as well as 17 km from Theater Of The Sea On Islamorada. Featuring a 24-hour front desk, this property also provides guests with a water park. Providing free WiFi throughout the property, the non-smoking holiday home features a spa centre. Windley Key is 18 km from the holiday home, while Pigeon Key is 34 km away. Key West International Airport is 116 km from the property. Show full description

Featuring a terrace with sea views, an outdoor swimming pool and a garden, Beacon Reef 222 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. Among the facilities at this property are a 24-hour front desk and a lift, along with free WiFi throughout the property. The property is non-smoking and is set 2.4 km from Upper Matecumbe Key. 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. Guests at the holiday home will be able to enjoy activities in and around Islamorada, like snorkelling. Windley Key is 3.1 km from Beacon Reef 222, while Pigeon Key is 19 km away. Miami International Airport is 118 km from the property. Show full description

Boasting a terrace with sea views, a spa and wellness centre and a garden, Beacon Reef 301 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. This beachfront property offers access to a balcony. Featuring free WiFi throughout the property, the non-smoking holiday home has a hot tub. 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. A water park is also available for guests at the holiday home. Upper Matecumbe Key is 2.4 km from Beacon Reef 301, while Windley Key is 3.1 km from the property. Miami International Airport is 118 km away. Show full description

Featuring a balcony with sea views, a spa and wellness centre and a garden, Beacon Reef 306 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. Boasting a 24-hour front desk, this property also provides guests with a water park. Providing free WiFi throughout the property, the non-smoking holiday home features a hot tub. The spacious holiday home comes 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. Upper Matecumbe Key is 2.4 km from the holiday home, while Windley Key is 3.1 km away. Miami International Airport is 118 km from the property. Show full description

Boasting a balcony with sea views, a spa and wellness centre and a garden, Beacon Reef 307 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. Featuring a 24-hour front desk, this property also provides guests with a water park. Featuring free WiFi throughout the property, the non-smoking holiday home has a hot tub. 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. Upper Matecumbe Key is 2.4 km from the holiday home, while Windley Key is 3.1 km from the property. Miami International Airport is 118 km away. Show full description

Boasting a balcony with sea views, a spa and wellness centre and a garden, Beacon Reef 310 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. Featuring a 24-hour front desk, this property also provides guests with a water park. Featuring free WiFi throughout the property, the non-smoking holiday home has a hot tub. The spacious 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. Upper Matecumbe Key is 2.4 km from the holiday home, while Windley Key is 3.1 km from the property. Miami International Airport is 118 km away. Show full description

Boasting a balcony with sea views, a spa and wellness centre and a garden, Beacon Reef 406 can be found in Islamorada, close to History of Diving Museum and 2.1 km from Theater Of The Sea On Islamorada. Featuring a 24-hour front desk, this property also provides guests with a water park. Featuring free WiFi throughout the property, the non-smoking holiday home has a hot tub. 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. Upper Matecumbe Key is 2.4 km from the holiday home, while Windley Key is 3.1 km from the property. Miami International Airport is 118 km away. Show full description