Florida Keys Vacation Rentals

Property 11-20 of 37

Bayfront Islamorada

Little Bay - Islamorada is famous for its amazing Sunsets and its incredible fishing. From this beautiful bay front home located in the heart of town, you can have both. Walking distance to all shops and restaurants but extremely quite and peaceful. Enjoy this 2 acre gated property with protected deep water dockage. This property consists of 3 separate living quarters; each one has 2 bedrooms and 2 baths. Living quarters may be rented separately or all together for a total of 6 Bedrooms / 6 Baths.

Bayfront Islamorada

Montelabre - Elegant, luxurious and very private estate home in a class of its own. Oversized heated swimming pool with Jacuzzi overlooking Florida Bay with an open-water sunset view. Deep-water dockage and davits accommodating boats up to 40 feet. Pick fruits from the private orchard within the grounds. Gated with full security system.

Bayfront Long Key

Layton Estate - MM 69, 3 bedrooms, 3 baths, sleeps 6-8. Wonderful sunset views over open water. Dock, swimming pool, charming large gazebo.

Oceanfront Islamorada

Acacia Point Estate - Enjoy this Elegant West Indies Inspired Estate Home with inspirational Ocean Views. This Estate has everything you would ever want for a fantastic get away to the place we call Paradise the Sunny Florida Keys.

Oceanfront Islamorada

Alligator Reef and Cottage - MM 84. 4 bedrooms, 3 baths main house, plus 3 bedroom 2 bath room cottage sleeps 12-14. Prices are for the 7 bedrooms, Main house also rented without cottage. Please inquire for rates on Main House Only. Beautiful oceanfront estate. Heated pool. Fishing and observation pier, kayak, putting green, horseshoes.

Oceanfront Islamorada

Aquazul - MM 87, 4 bedrooms, 3 baths, sleeps 8-10. Captivating oceanfront home with heated pool and deepwater dock. Gated. Amenities include 2 kitchens. High-speed internet.

Oceanfront Islamorada

Atlantic Utopia - Enjoy the spectacular views from every room in this exquisite dream home, located on one of the finest beaches in the Florida Keys. Watch both the sunrise and sunset from every room and balcony. Complete with everything you could possibly need on your vacation getaway, this home comes with elevator for easy access, deep water dockage, a boat lift and electricity at the dock, fish cleaning station, gourmet kitchen, game room with pool table, work out equipment, wireless internet. The house is gated and private and is located just minutes away from all the shops and restaurants.

Oceanfront Islamorada

Beachside Bungalow - MM 88.7, 3 bedrooms, 3 baths, sleeps 8-10. Captivating tropical home. Gated for privacy. Florida room upstairs spanning entire length of house with spectacular open-water sunrise views. Beautiful heated pool. Generous 360 foot dock with 5 foot depth at low tide.Dock access to sandy ocean bottom. High-speed internet.

Oceanfront Islamorada

Blue Harbour Retreat - MM 85, 4 bedrooms, 3 baths, sleeps 8-10. Protected deep-water dock with easy access to both ocean and bay, swimming and boat basin. Private. Magnificent sunrises and oceanfront vistas.

Oceanfront Islamorada

Casa Blanca - This Amazing 3+ Acre Property offers open water views, 360 foot dock with deep water dockage, heated swimming pool and Jacuzzi. Comes equipped with a modern kitchen, flat screen TV, high-speed internet, elevator, Tennis Court and much more...