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Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.

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25
3
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Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
2 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Parking available

Explore the area

View map
Islamorada, FL
  • Place, Founders Park
    ‪8 min walk‬
  • Place, Rain Barrel Village
    ‪18 min walk‬
  • Place, Old Road Gallery
    ‪2 min drive‬

Rooms & beds

2 bedrooms (sleeps 8)

Bedroom 1

1 King Bed

Bedroom 2

2 Single Beds

3 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Spaces

Kitchen
Kitchenette
Balcony
Dining area

About this property

Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.

Leatherback Cottage - The Leatherback Cottage is located in Turtle Cove, Islamorada's quaint enclave of five cottages all with their own personality and characteristics. All five cottages share the property's amenities: pool, boat basin, tropical sprawling grounds, ping pong table, kayaks, paddle boards and more. The main living area is located on the upper level of this oceanfront cottage and has open ocean views throughout. The open concept kitchen, living and dining room are great for entertaining. The main level has two bedrooms and two baths. The lower level is a separate living area with 2 sets of bunk beds, a living room, kitchenette and bathroom. It can be added when renting the upstairs for an additional $600 weekly. The Leatherback Cottage can be rented separately or in combination with any of the four other homes.
VACATION RENTAL LICENSE: 24-0386
If booking more than a year in advance current prices may not reflect the 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.

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.

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10.0 out of 10, Exceptional, (117 reviews)
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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Adults only
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Events

No events allowed
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Pets

No pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has not indicated whether there is a smoke detector on the property
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room

About the area

Islamorada

Islamorada is home to this holiday home. Florida Keys Dive Center and Mangrove Marina are worth checking out if an activity is on the agenda, while those looking for area attractions can visit John Pennekamp Coral Reef State Park and MoradaWay Arts & Cultural District.
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Map
Islamorada, FL

What's nearby

  • Founders Park - 8 min walk - 0.7 km
  • Rain Barrel Village - 18 min walk - 1.5 km
  • Old Road Gallery - 2 min drive - 2.7 km
  • Theater of the Sea - 5 min drive - 6.3 km
  • Bud n' Mary's Dive Center - 13 min drive - 15.9 km

Getting around

  • Miami International Airport (MIA) - 100 min drive

Restaurants

  • ‪McDonald's - ‬6 min drive
  • ‪Dillon's Pub & Grill - ‬6 min drive
  • ‪Tiki Bar - ‬5 min drive
  • ‪Hog Heaven - ‬4 min drive
  • ‪Twisted Shrimp - ‬4 min walk

Frequently asked questions

Is Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada. pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.?

As of 29 March 2026, prices found for a 1-night stay for 2 adults at Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada. on 9 May 2026 start from NZ$1,060, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.?

On-site parking is available at the property.

What time is check-in at Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.?

Check-in begins at 4:00 PM.

What time is check-out at Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada.?

Checkout is at 10:00 AM.

Where is Leatherback Cottage: Adorable 2-bedroom oceanfront pool home with open water views in Islamorada. located?

Situated in Islamorada, this holiday home is within 1 mile (2 km) of Islamorada County Park, Rain Barrel Village and Founders Park. Old Road Gallery and Windley Key Fossil Reef Geological State Park are also within 3 miles (5 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 17 out of 17 reviews
Rating 8 - Good. 0 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 0 out of 17 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Mike A.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Leatherback Cottage was Awesome!

The house was great! Right on the water and especially great if you are bringing a boat down, with two boat lifts. Property Manager, Sue, was great to work with, and she always responded quickly. Just note that if you plan to use the downstairs area, it’s 600/wk and that’s not included in the listed price. It mentions this in the description, but it is very easy to miss, like we did. Overall, though, we loved the place and would stay here again.
Stayed 7 nights in Feb 2025
Verified

10/10 Excellent

Lisa W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful location

Lovely, clean accomodations. Beautiful sunrise viewing from the deck as well as loads of birds visiting daily. Our host was readily available and very helpful. Highly recommend this property.
Stayed 10 nights in Dec 2024
Verified

10/10 Excellent

Jim B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

**Escape to Paradise: A Serene Retreat in Islamorada**

Nestled in the serene beauty of Islamorada, this vacation rental offers an idyllic escape for those seeking waterfront tranquility. From the moment you arrive, the breathtaking views of the shimmering waters invite you to unwind and embrace the laid-back atmosphere of the Florida Keys. Security is paramount, and guests can rest assured knowing that this rental provides a safe and secure environment for a worry-free stay. Whether you're lounging on the private deck or strolling along the palm-lined property, peace of mind comes naturally in this secluded oasis. Tranquility abounds in every corner of this retreat, where the only sounds you'll hear are the gentle lapping of waves and the rustle of palm trees in the breeze. Whether you're savoring morning coffee on the private deck or enjoying an evening cocktail by the water's edge, the serene ambiance envelops you, offering a respite from the hustle and bustle of everyday life.Surrounded by swaying palm trees and bathed in the warm glow of the Florida sun, this rental embodies the essence of relaxation. Whether you're lounging by the pool or swaying in a hammock, every moment here is an opportunity to rejuvenate the mind, body, and soul. In summary, this vacation rental in Islamorada offers a blissful retreat where waterfront serenity, security, tranquility, and relaxation converge, creating an unforgettable escape for those seeking solace amidst the beauty of the Florida Keys.
Stayed 9 nights in Feb 2024
Verified

10/10 Excellent

Christine N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Another Amazing Stay

This was our 3rd summer staying here and it gets better every year. Sue is always available and the home and property have everything and anything you could need. We are already looking forward to next summer.
Stayed 8 nights in Jun 2023
Verified

10/10 Excellent

Kelly B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect cottage

Perfect location in the keys! We absolutely enjoyed every minute at Leatherback Cottage, it was exactly as pictured and couldn’t have been a more beautiful location! The pool was relaxing, my boys fished off of the dock, and close to the store and restaurants. Sue was attentive and fantastic to work with, couldn’t have asked for anything else! Highly recommend this property!
Stayed 7 nights in Mar 2023
Verified

10/10 Excellent

Amanda L.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property and Great Location. Sue with Freewheelr vacations was amazing and very accomadtin

Beautiful Property and Great Location. Sue with Freewheeler vacations was amazing and very accomadating.
Stayed 10 nights in Jul 2022
Verified

10/10 Excellent

Christine N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful Property

This was our second time staying here and it was just as great as the first time. Plenty of room for the boat. Clean pool and beautifully landscaped property. Comfortable beds and everything you could need in the kitchen. We can't wait to come back.
Stayed 8 nights in Jun 2022
Verified

10/10 Excellent

Beth F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect Stay

Staying at the Leather Back cottage was amazing. The house was very comfortable with many amenities. The incredible view offers peace and tranquility! The pool provided a refreshing dip late in the afternoon. The tropical grounds are beautiful and well maintained. Centrally located to restaurants, shops and nightlife!
Stayed 7 nights in Apr 2022
Verified

10/10 Excellent

Jim B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Islamorada Vacation House

This property is perfect for a couple or small family, the house is nicely remodeled and furnished comfortably. There is a well stocked kitchen with plenty of dishes, glasses and cookware. Nice newer appliances and a separate drink fridge. The gated complex has lots of plants and trees and provides a private and tropical vacation. I wish I could stay forever.
Stayed 9 nights in Feb 2022
Verified

10/10 Excellent

Josh and Heather S.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Perfect

We loved everything about the house and the property. Above our expectations and a wonderful quiet getaway week with beautiful views and close to fishing.
Stayed 8 nights in Feb 2022
Verified

10/10 Excellent

Michael D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Exceptional Property

Family stayed at this exceptional property for 9 days. Rented both upper and lower levels. Clean and very well provisioned both with household items and water toys (4 kayaks, 2 paddle boards, lots of life vests, pool toys, etc). Sue was attentive, helpful, friendly. The quay and cabana offer unrestricted water and sky views, fantastic on moonlit nights. Elegant landscaping and clean pool (shared with folks from other rental homes on the property). Marine life passing by included turtles, snook, tarpon, barracuda and nurse sharks. Importantly renters have free access to nearby Founders Park, which has a well-staffed 50 meter pool, open playing fields and a pleasant little beach with shallow depths appropriate for families with small children. Snorkel beyond the beach at Founders and you're living the full Jacques Cousteau experience, dozens of fish species in shallow water. Plenty of nearby fishing/scuba/snorkel operators, with submerged remains of Spanish galleons from the 1733 plate fleet near shore. Plenty of decent restaurants and boutique shops within a short drive. With its own little port (good channel + day markers + mean tide depths to hold boats I would guess to 26 feet though perhaps more), this is an excellent base for fishers and divers. Intend to return.
Stayed 9 nights in Dec 2021
Verified

10/10 Excellent

Julie F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Beautiful property - better than advertised

We loved the house, the property, and the amenities. Everything advertised was there and more. The property management was extremely responsive. We look forward to returning.
Stayed 7 nights in Jul 2021
Verified

10/10 Excellent

Christine N.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Gorgeous Property and Home!

The pictures simply don't do this place justice. It's absolutely beautiful! Clean, comfortable beds and couches, everything you could need in the kitchen, and everything is updated. The pool is clean and warm with plenty of lounge chairs. There are so many toys for the property to share like fishing poles, kayaks and noodles. The downstairs has bunk beds and so much space to hang out. Perfect for the kids. Plenty of room to park the boat and trailer. I had a few questions for Sue and my calls were returned within minutes. I wish we could have stayed longer but we will definitely come back.
Stayed 7 nights in Jun 2021
Verified

10/10 Excellent

Joleen D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great Stay!

Thanks Sue for always being available to answer any questions.
Stayed 7 nights in May 2021
Verified

10/10 Excellent

Kathy T.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Leatherback spring break 2021

We had the best stay at the Leatherback home on Islamorada. The home is so lovely and well appointed. The views were so beautiful and the location is convenient to many of the marinas if you are like us and didn’t have a boat to dock. But if you have a boat, this is the place for you! The saltwater pool is great! It is shared between the 4 houses in this gated group which I don’t think was disclosed on the listing but it was of course fun to talk to others who were also visiting. This property would be great to book for a group of friends or family who want to be together but maybe not every second. The four adorable houses would be perfect for that. This home has everything you need for water sports as well, kayaks and lots SUPs, life jackets and even some fishing poles! Sue, the property manager, is quick to respond and was so friendly. We truly enjoyed our stay and hope to return again.
Stayed 7 nights in Apr 2021
Verified

10/10 Excellent

Timothy W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Paradise!

Property location was a slice of paradise. Home was well furnished and had everything. Video game did not work, which is why I marked down the accuracy of the online representations. However, property had kayaks, paddle boards, and other amenities not advertised. Overall excellent. We will be back.
Stayed 7 nights in Jun 2020
Verified

10/10 Excellent

tomwwagner

Liked: Cleanliness, check-in, communication, location, listing accuracy
Stayed 7 nights in Jan 2025

About the host

Hosted by Sue at Freewheeler Vacations

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