Turtle Crawl on Long Key Oceanfront Beachfront with dock and pool

Turtle Crawl – Magnificent Oceanfront Estate Home

Discover the very best of the Florida Keys at Turtle Crawl, a breathtaking oceanfront estate where upscale design meets barefoot luxury island living. Located on scenic Long Key, this private luxury retreat sits on nearly one acre of pristine tropical paradise, featuring a real sandy beach, panoramic views of the Atlantic, and direct boating access to both the Gulf and Ocean via the nearby Long Key Bridge.

This expansive 5-bedroom, 5-bath estate home offers over 5,000 square feet of beautifully appointed living space, with cathedral ceilings, a vast great room, and a layout that’s ideal for entertaining and relaxing in style. Whether you're traveling with family, friends, or celebrating a special occasion, Turtle Crawl delivers a once-in-a-lifetime vacation experience.

Luxury Features & Amenities

Real sandy beach with protected turtle nesting areas (outdoor lights off at 10 PM to preserve nesting activity)

Massive 40-foot resort-style pool surrounded by swaying palms and stunning ocean views

Expansive covered veranda for oceanfront dining, morning coffee, or evening cocktails

Private dock with a 4-ft draft, perfect for fishing or launching your boat

Kayaks and Paddleboards included.

Spacious concrete construction with privacy and safety in mind

Five luxurious bedrooms, all with king-size beds and big-screen TVs

Four en suite bathrooms, plus a fifth full bath to accommodate the 5th bedroom.  4 of the bedrooms are on the main floor. 

Third-floor entertainment room with access to a widow’s walk for panoramic ocean and island views

Fast, direct boating access to both the Atlantic and the Gulf of Mexico

Tons of natural light and views from nearly every room

Whether you're soaking up the sun by the pool, fishing from the dock, or watching stars emerge over the water, every moment at Turtle Crawl feels like a dream come true.

Explore Long Key & the Middle Keys

While the home is designed for you to never want to leave, there’s plenty to explore nearby! Located midway between Islamorada and Marathon, Long Key is the perfect launchpad for adventure.

Nearby Restaurants (within a short drive):

Habanos on the Creek – Authentic Cuban cuisine and fresh seafood in a laid-back waterfront setting.

Lobster Crawl Bar & Grill – Located just up the road with great ocean views, cocktails, and island fare.

Lazy Days (Islamorada) – One of the top-rated spots in the Keys, offering oceanfront dining and bring-your-catch options.

Island Fish Company (Marathon) – A classic Keys tiki restaurant with a full bar and fresh daily catches.

Morada Bay Beach Café (Islamorada) – Stunning dining on the beach with an upscale island vibe and signature cocktails.

Things to Do Nearby:

Long Key State Park – Kayak through mangrove trails, hike coastal hammocks, or simply enjoy a serene picnic on the beach.

Fishing Charters – Book a guided trip for world-class tarpon fishing just minutes away.

Diving & Snorkeling – Explore vibrant coral reefs at Coffins Patch or Alligator Reef, both short boat rides away.

Paddleboarding & Kayaking – Calm waters make this the perfect area for exploring by paddle.

The Dolphin Research Center (Grassy Key) – A fantastic, family-friendly experience for up-close dolphin interactions.

The Turtle Hospital (Marathon) – Learn about sea turtle rescue and rehabilitation at this beloved local nonprofit.

Bahia Honda State Park – Just a short drive south, offering some of the best beaches and snorkeling in the Keys.

After a day of exploring, return to Turtle Crawl, where the pool awaits, the ocean breeze calls, and the stars shine bright over the Atlantic.

Let us help you create your dream vacation in the Florida Keys! We’re happy to accommodate most special requests and are committed to making your stay at Turtle Crawl unforgettable.

Max Occupancy: 12 - (No exceptions)

- Must be 25 years or older to book and must be present for the entire stay

- Max occupancy reflects the number of guests allowed per city regulations and does not guarantee sleeping accommodations for that number—please review the bed description carefully

-Occupancy includes children and infants

28-night minimum (No exceptions)

Check-in:

4:00 PM on the day of arrival (please note during high season, check-in may be delayed until 5:00 PM)  

Check-out:

10:00 AM on the day of departure

Dockage is available at this property; please verify maximum boat size and dockage details with the property manager prior to booking

Vacation Rentals of the Florida Keys provides a complimentary starter set of items, including soap, toilet paper, paper towels, dishwasher detergent, and laundry detergent, etc. Guests are responsible for providing additional supplies for the remainder of their stay. Starter items are typically located in the bathrooms, at the kitchen sink, and in the laundry area. Some properties may also include a small welcome basket or additional guest amenities.

Linens and bath towels are always included.

This property is not pet-friendly, Failure to disclose a pet may result in additional charges up to $500 and immediate eviction without refund.

Enhance your stay with our concierge services, designed to create a seamless and memorable Florida Keys experience. Our concierge agent, Kasey Platt, can assist with everything from private boat charters, snorkeling, fishing trips, and eco-tours to in-home massages, private chefs, and unique entertainment like fire shows or dancers. She can also help arrange grocery deliveries, kayak or fishing gear rentals, charcuterie boards, and more.

Born and raised in Marathon, Kasey has strong local connections, allowing for personalized recommendations and exclusive experiences. More details on available services and how to coordinate them are shared with guests after booking. If you have any questions in advance, please let us know—we’re happy to help!

Vacation Rentals of the Florida Keys (Vrotfk) has Terms and Conditions that apply to this property and all properties we manage. By booking this property—whether directly with us or through a third-party site—you and your party expressly agree to these Terms and Conditions. A deposit or completed booking serves as acknowledgment and acceptance of these terms. After your reservation is confirmed, the Terms and Conditions will be sent to you via an e-sign document, which is required to be completed. If the e-sign is not completed, access to the virtual guidebook and arrival details will not be provided. Please feel free to reach out with any questions. Additionally, we will request certain information that third-party sites may not collect, as we are required to have specific details on file per company policy and local city regulations.

For any questions or concerns, or just want to talk after booking, please reach out to your agent directly.

Amenities Include:

- Air Conditioning: Yes

- Kitchen: Fully Equipped

- Private Entrance: Yes

- Smoke Detector: Yes

- Bait Freezer: Yes

- Bed Size 1st/Master: King Ground level with On Suite bath

- Bed Size 2nd Rm: King Ground level with On Suite bath

- Bed Size 3rd Rm: King Ground level with On Suite bath

- Bed Size 4th Rm: King Ground Level, shared bath

- Bed Size 5th Rm: King Upper level with On Suite bath & Twin Bed

- Child Friendly: Yes

- Coffee Maker: Drip

- Dockage: 3 ft draft max 25 ft boat outboards

- Kayaks: 4 kayaks

- Paddleboards (Sup): 2 paddleboards

- Pool: Heated Private

- Balcony: Yes Oceanfront

- Bbq Grill: Yes

- Ceiling Fans: Yes

- Internet Access: Yes

- Micro/Dishwash/Disp.: Yes

- Patio: Yes Oceanfront

- Refrig And Ice Maker: Yes

- Square Footage, Est.: 5050 sq ft

- Stove/Oven Elec/Gas: Electric

- TV Cable/Satellite: Yes Cable Ready and Streaming

- TVs/Vcr/Dvd: Every room has a big screen tv.

- View: Oceanfront Southeast exposure

- washer dryer: Yes