Set on nearly three private acres with 200 feet of secluded Atlantic shoreline, The Oasis is a truly rare Islamorada estate offering space, privacy, and one of the most unique features in the Florida Keys — a heated saltwater pool positioned directly on the ocean itself.

This exclusive compound consists of two separate homes, thoughtfully designed for comfort and flexibility. The main residence offers one bedroom and 1.5 baths, while the guest house features two bedrooms and one bath. Each home includes its own kitchen and living area, allowing families or groups to gather together while still enjoying private space when desired.

The grounds are expansive and beautifully maintained, framed by towering palms and open water views in every direction. Spend your days launching one of the four kayaks or two paddleboards from your private beach, cruising the neighborhood on one of six bicycles, or enjoying a game of bocce ball or cornhole as the ocean breeze rolls in.

Modern comforts are seamlessly integrated throughout, including enterprise-grade high-speed Wi-Fi, a Tesla charging station, professional mosquito control service, five 50” smart TVs, and stainless steel appliances.

Pet friendly and ideally located in the heart of Upper Matecumbe — just 0.7 miles from Publix and minutes from Islamorada's best dining, marinas, and sandbars — The Oasis delivers something exceptionally hard to find in the Keys: acreage, beachfront, an oceanfront pool, and total privacy, all in the center of town.

If booking more than a year in advance current prices may not reflect annual cost of living increase.
Many of our guests' re-book the same property on an annual basis. No reservation is confirmed until you speak with us.
VACATION RENTAL LICENSE: 24-0120 Per Islamorada's vacation rental ordinances for weekly rentals 2 people per bedroom are allowed, and 2 additional guests if under the age of 6.

Please note: before proceeding with your booking, kindly review the following information. This property is managed by a local Islamorada rental company, Freewheeler Vacations. Payments for your vacation rental will be made thru Freewheeler Vacations. You will also see a charge from VRBO which covers their booking service fee which is already included in the total cost. We prefer payments via personal check or eCheck. However, if you opt to pay by credit card, a 3% convenience fee will be applied to your rental. You will receive the Freewheeler Vacations Vacation Rental Agreement via email, which must be signed before your arrival. All future correspondence will be made through Freewheeler Vacations.