Oceanfront Estate - Private Beach, Pool, & Dock

Top rated by guests
Pool
Dining
Dining
Oceanfront lush tropical grounds, a private pool & private beach!
Bring Your Boat! Please read our Boat Docking Information before booking.
review stars
10Outstanding
(4 Ratings)
"This is an awesome location!! We had such a great time swimming in the ocean and the pool everyday! The kayaks were so much fun too. The house was perfect for us too!. I have zero complaints! Would hi..."
STEVE S.
Don't miss out! Price and availability may change
10 / 10
Outstanding(4 Ratings)

House in Upper Matecumbe Key, FL

12 guests · 5 bedrooms · 4 baths

Reasons to book

Guests love it hereGuests give this property a top rating
Top-tier experienceA high end property in this area
Book with confidenceWe partner with the top travel sites so you know you're getting a great deal on the perfect rental

About this house rental

Palm Escape – A Private Oceanfront Tropical Estate in the Heart of Islamorada

Private Estate - Beach, Pool, & Dock all fully Private!

Welcome to Palm Escape—where towering palms, lush tropical gardens, and breathtaking ocean views create one of the most private and unforgettable waterfront retreats in the Florida Keys.

From the moment you arrive through the gated entrance, you're surrounded by vibrant tropical landscaping that makes the property feel more like a secluded island resort than a vacation rental. Guests often say the grounds are even more spectacular in person, creating an atmosphere that's peaceful, private, and unlike anywhere else in Islamorada.

Whether you're sipping coffee beneath the palms as the sun rises over the Atlantic, lounging beside the heated oceanfront pool, launching a kayak from the shoreline, or docking your boat in the protected private basin, every part of the property is designed to help you slow down and enjoy the Keys the way they were meant to be experienced.

The estate comfortably accommodates families and groups with five beautifully appointed bedrooms, spacious indoor gathering areas, and a separate guest cottage that provides additional privacy while keeping everyone together on one spectacular property.

After a day on the water, gather for dinner on the outdoor patio, grill your fresh catch, relax beneath the stars, and fall asleep to the sound of gentle ocean breezes.

Located in the heart of Islamorada, Palm Escape is just minutes from world-class fishing, diving, snorkeling, waterfront restaurants, local breweries, boutiques, and everything that has made the Florida Keys famous—yet once you're inside the gates, it feels like your own private tropical sanctuary.

Highlights
Private oceanfront estate in the heart of Islamorada
Exceptionally lush tropical landscaping that creates unmatched privacy
Heated oceanfront swimming pool
Private sandy beach
Protected private boat basin and dock
Four bedrooms plus separate guest cottage
Fully equipped kitchen
High-speed Wi-Fi
Smart TVs with streaming services
Outdoor dining area with BBQ grill
Kayaks for guest use
Outdoor shower
Two dedicated workspaces

Boat Docking Information

Yes — You Can Bring Your Boat
We welcome boats up to 30 feet at our private boat basin.

Boats regularly enter and leave the basin successfully. The only requirement is that, like many waterfront homes throughout the Florida Keys, you must plan your arrivals and departures around the tides.

Please note: During extremely low tides, the basin can become so shallow that many boats will rest on the bottom until the tide returns. This is a normal occurrence in many shallow-water areas of the Florida Keys and typically lasts only a short period before the water rises again.

Understanding the Tides

Water depth changes throughout the day as the tide rises and falls.

High tide provides the greatest water depth.

Mid to high tide is generally the best time to enter or leave the basin.

During low tide, only shallow-draft boats (such as flats boats, bay boats, or certain Boston Whalers) may have sufficient clearance.

Boats with deeper drafts should simply plan departures and returns around the tide schedule.

Water Depth - The water depth in front of the house is anywhere from 1 to 3 ft depending on the tides.

Minutes from the Keys' best restaurants, marinas, fishing, diving, and snorkeling
Whether you're planning a multi-generational family vacation, a fishing adventure, or simply looking for a peaceful escape surrounded by natural beauty, Palm Escape offers the rare combination of luxury, privacy, and authentic Florida Keys charm that keeps guests returning year after year.

Amenities

Non-smoking
No pets allowed
Family friendly

Map of Upper Matecumbe Key, FL


Ratings and reviews

10 / 10
Outstanding(4 Ratings)
10 / 10Outstanding·Mar 2026
This is an awesome location!! We had such a great time swimming in the ocean and the pool everyday! The kayaks were so much fun too. The house was perfect for us too!. I have zero complaints! Would highly recommend! Islamorada is a perfect location to see the entire Keys!
10 / 10Outstanding·Feb 2026
We had a Fabulous vacation! The home is beautiful and the pool was thoroughly enjoyed. Close to restaurants, shops, boating,and groceries. You can even get door dash and Amazon deliveries. Zana,the goto for assistance was awesome. The hosts were also available for any questions. We are already talking about going next year hopefully with a few more family members.
10 / 10Outstanding·Oct 2025
Upon arrival, we were amazed at the beauty of the location of the home. Everything was in prestine condition. The pool and beach are minutes away from the back door. We experienced a plethora of restaurants on the island. The owners were wonderful to work with. We definitely will be returning.

$$$$
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FAQs

Is parking included with this house?

Parking is not specified as an available amenity at Oceanfront Estate - Private Beach, Pool, & Dock. For more information, we encourage you to contact the property about where to park.

Is there a pool at this house?

We didn’t find pool listed as an amenity for this house. It may be worth double checking if a pool is important for your stay.

Is Oceanfront Estate - Private Beach, Pool, & Dock pet friendly?

Unfortunately, this house is not pet-friendly. Try searching again and filter for "Pets Allowed"

What amenities are available at Oceanfront Estate - Private Beach, Pool, & Dock?

We found 3 amenities for this rental. This includes non-smoking, no pets allowed, and family friendly.


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