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Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.

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Reviews

8.4 out of 10
Very good
4 bedrooms4 bathroomsSleeps 10

Popular amenities

  • Private pool
  • Onsite parking available
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Outdoor barbecue

Explore the area

View map
Islamorada, FL
  • Place, Sunset Drive Beach
    ‪2 min drive‬
  • Place, Robbie’s of Islamorada
    ‪3 min drive‬
  • Place, Anne's Beach
    ‪3 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪39 min drive‬

Rooms & beds

4 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

1 Double Bed

Bedroom 4

2 Single Beds and 1 Double Bed

4 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Bathroom 3

Toilet · Shower only

Bathroom 4

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.

Step through the gates of this stunning oceanfront estate and instantly feel the tranquility of the Florida Keys. Surrounded by lush tropical landscaping and cooled by steady ocean breezes, this French Caribbean–style home feels like your own private island retreat.
The property features an incredible oceanfront setting with a private beach, expansive porches perfect for sunrise views, and a large infinity pool overlooking the Atlantic. A unique saltwater pond and beautifully landscaped grounds create a peaceful, resort-like atmosphere throughout the property.
The main home offers three bedrooms and three full bathrooms along with a den and gourmet kitchen designed for gathering and entertaining. The second floor includes the spacious primary suite with a king bed and a guest bedroom also furnished with a king bed. The third floor features a cozy bedroom with a queen bed and a loft area with two twin beds, perfect for additional guests.
A charming beachfront guest cottage provides additional privacy with its own bedroom and full bath, complete with a queen bed.
Guests will enjoy amenities including Wi-Fi, TVs, a BBQ grill, beach chairs, kayaks, and paddleboards—perfect for exploring the surrounding waters and enjoying the laid-back island lifestyle. Multiple outdoor spaces throughout the property allow you to fully take in the oceanfront setting.
Located in the heart of Islamorada, the Sportfishing Capital of the World, you'll have easy access to world-class fishing, snorkeling, diving, art galleries, shopping, and some of the best restaurants in the Florida Keys.
This extraordinary property is more than just a vacation rental — it's a true Keys escape.
VACATION RENTAL LICENSE: 24-0390
If booking more than a year in advance, current rates may not reflect future cost-of-living adjustments. Many of our guests return year after year to enjoy this special property. No reservation is confirmed until you speak with us.
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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House Rules

Check in after 3:00 PM
Minimum age to rent: 22
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 indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
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

Matecumbe, a neighbourhood in Islamorada, is home to this holiday home. San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park are local landmarks, and the area's natural beauty can be seen at Long Key State Park and Windley Key Fossil Reef Geological State Park. Looking to get your feet wet? Scuba diving, snorkelling and surfing/body boarding adventures can be found near the property.
View more Holiday homes in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 2 min drive - 2.3 km
  • Robbie’s of Islamorada - 3 min drive - 3.3 km
  • Anne's Beach - 3 min drive - 4.3 km
  • Indian Key Historic State Park - 4 min drive - 4.3 km
  • Bud n' Mary's Dive Center - 7 min drive - 8.3 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 30 min drive

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬3 min drive
  • ‪Lazy Days Restaurant - ‬5 min drive
  • ‪Papa Joe’s Waterfront - ‬5 min drive
  • ‪Islamorada Fish Company - ‬7 min drive
  • ‪Morada Bay - ‬8 min drive

Frequently asked questions

Does Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada. have a pool?

Yes, this property has a pool. Pool types include heated pools.

How much does it cost to stay at Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.?

As of 30 April 2026, prices found for a 1-night stay for 2 adults at Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada. on 1 August 2026 start from NZ$1,849, 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.

Is Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada. pet-friendly?

No, pets are not allowed at this property.

How much is parking at Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.?

On-site parking is available at the property.

What time is check-in at Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.?

Check-in begins at 3:00 PM.

What time is check-out at Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada.?

Checkout is at 10:00 AM.

Where is Experience paradise at 75731 Overseas Highway, a stunning 4-bedroom retreat in Islamorada. located?

Located in Matecumbe, this holiday home is steps away from Anne's Beach and Sunset Drive Beach. San Pedro Underwater Archaeological Preserve State Park and Robbie’s of Islamorada are also within 2 miles (3 km).

Reviews

8.4

Very good

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
Learn moreOpens in a new window
Rating 10 - Excellent. 10 out of 21 reviews
Rating 8 - Good. 7 out of 21 reviews
Rating 6 - Okay. 2 out of 21 reviews
Rating 4 - Poor. 2 out of 21 reviews
Rating 2 - Terrible. 0 out of 21 reviews

8.0/10

Cleanliness

9.6/10

Check-in

9.6/10

Communication

9.4/10

Location

9.2/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Wendy B.

Liked: Cleanliness, check-in, communication, location, listing accuracy
The house was full of charm. Very clean. A really fun place to stay!
Stayed 10 nights in Feb 2026
Verified

10/10 Excellent

Kriste C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Very responsive host, pool and beach was amazing. Had 10 people and we had plenty of room. We had an amazing vacation, house and land was absolutely amazing! Hung out on back patio and pool or beach the entire vacation, literally couldn’t get the family to leave the property.
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Jen L.

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

Amazing

Everything was great! Loved the pool!
Stayed 7 nights in Mar 2025
Verified

8/10 Good

Suzanne A.

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

Family vacation

We had a great time. House was lovely. FYI refrigerator in beach house does not work.
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Ben H.

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

Beautiful Moonrises!

We stayed with two families, there is plenty of room to spread out across the property. It lived up to all expectations, the outdoor areas including pool and beach and wonderful! The house is stocked with bikes, kayaks, paddleboards, floats, etc. We look forward to our return visit soon!
Stayed 8 nights in May 2024
Verified

10/10 Excellent

Rob B.

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

Wonderful stay in Islamorada

We enjoyed our stay on the Atlantic side, Lower Matecumbe, a few miles down the highway from Islamorada, Bud & Mary’s, and Robbies. The pool is nice and the large gently sloping private sandy beach with boats and paddleboard is a plus. The sandy bay is shallow and calm. Saw a dolphin in it one morning. Restaurants and amenities are all within an easy drive. We day-tripped to Key West - about a two-hour drive. Thank you to our professional hosts!
Stayed 7 nights in Mar 2023
Verified

8/10 Good

Tina r.

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

Beautiful home in need of maintenance and upgrades

Beautiful home Great location Lots of maintenance issues Had to do some cleaning Water between main house and guest house is nasty Some things need to be upgraded
Stayed 7 nights in Jun 2022
Verified

10/10 Excellent

Thomas G W.

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

Amazing Property!

We rented this property to attend my niece's wedding in the area. The house (and its separate cottage) comfortably accommodated (with enough room for occasional privacy) our multigenerational family of ten, from my 6 month old granddaughter to my 85 year old father-in-law. All of the amenities, including kitchen for meal prep, patio and pool, private beach, kayaks and paddleboards, etc, etc, etc. The Freewheeler Team quickly addressed the few questions we had during our stay. Oh, and my nearly 3 year old granddaughter absolutely loved the iguanas and other wildlife!
Stayed 7 nights in Dec 2022
Verified

6/10 Okay

Robin S.

Liked: Cleanliness, check-in, communication, location

Older spacious home with great views and extensive landscaping

The home has tremendous charm and potential and the grounds are wonderful. The furnishings are comfortable and plentiful and everything we needed was in working order. The house does need many updates but the artwork, pool and landscaping are all a big plus. Our family enjoyed the many amenities and the variety of activities nearby. The views from the pool and decks are also amazing. We were not aware of the large amount of seaweed at the shoreline and in the water and there was a frequent unpleasant odor from the seaweed brought in by winds and wind shifts, so we didn’t use the beachfront as often as planned. There actually isn’t a spa as noted in the property description. The property manager(s) were extremely pleasant and responsive the couple of times we needed assistance and we would definitely rent properties through them again.
Stayed 8 nights in Jun 2021
Verified

6/10 Okay

Tanya B.

Liked: Check-in, communication, location

Quaint Beach Property

First the Pros: This is a large home and can accommodate large families. Lots of space for privacy for different parties staying. Upon arriving the house the exterior is lovely with it’s circular drive and vintage feel. Overall interior decor was about a 3.5 star rating considering it’s older and a few things are outdated. The landscaping is well done. Bikes were provided. The separate cottage 20’ feet from the beach was darling. Enjoyed sitting by the beach in the provided chairs and hammock. The pool is very nice. Enjoyed the living room sofa with its back massagers. However, there are a few issues. Cons: While the house was clean, it was fairly clean. We had to buy a coffee maker because the one provided was horrible and unusable. Chairs in kitchen area were dirty from food spills. Interior cabinets in kitchen were dirty and cluttered. Pullout of drink holder on sofa was dirty and had food in it. Towels and linens provided are older and dingy. No beach towels are provided. Baseboards in some areas were gross. Clutter including a ladder just thrown on the side back porch. I found this unreasonable. Landscape pots just tossed under shrubs. Closets, pantry and cabinets are full of clutter. Masterbath tub was not cleaned. Master shower has paint peeling from ceiling and some mildew on tiles. Considering this is a rental and understanding how people treat rentals I tried to be objective but stairway also needs painting. Serious Algea bloom in pond. A few of iguanas over two feel long occupy the pond. While we found them amusing but I would recommend getting rid of them before the get any larger. While this is probably not entirely the property management problem, the beach was a foot deep in seaweed. Plastic bottles and straws and random flipflops and other litter were present. Effort could have been made to at least rake the beach. But it was apparent this is an ongoing problem since neighbors on either side was worse with tons of litter and in some areas two feet deep of seaweed present. Furniture is not new and in some areas not placed correctly. Master bedroom had two ummatched dressers placed side by side which was strange. Outdoor furniture is older. Pool was ok clean but still had dirt in it. My overall rating is 3.5. House needs a deep cleaning, organizing/declutter, and better linens.
Stayed 7 nights in Sep 2020
Verified

10/10 Excellent

Carol B.

Liked: Check-in, communication, location, listing accuracy

Spring break with the family!

We’ll be back!! All the outdoor amenities are the best!!
Stayed 7 nights in Mar 2022
Verified

10/10 Excellent

Blair G.

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

Loved it!

My whole family had a great time at Markeysa. The beauty and tranquility of the place struck us the minute we came through the front gate. The property is very private and beautifully landscaped, and the house itself is like an art gallery. The property manager was very personable and responsive. When we mentioned that the coffee maker was a little small for our family, he brought us a brand new one the same day! I definitely would like to come back to Markeysa.
Stayed 7 nights in Feb 2022
Verified

4/10 Poor

Jack J.

Liked: Check-in, communication, listing accuracy
Disliked: Location

Needs a lot of TLC!

Outdated!
Stayed 7 nights in Jul 2021
Verified

8/10 Good

Levonne L.

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

If you love Islamorada this is the house for you

This was our first trip to the Keys and so our first impression of the house did not disappoint. Upon entering the gate, you see a beautiful Key West style house with lush landscaping and inside, you see the gorgeous view of the pool, beach and ocean beyond. The kitchen is well appointed with a high end oven, two fridges and lots of pantry space. The master bedroom is spacious and has a balcony facing the ocean. However, the third floor does not have a bathroom and the “bedroom” with the twin beds is really a space at the top of the stairs with no door. The main level bathroom is large (with a shower) that can be entered from the pool deck. The pool is large and the pool deck has lots of seating but the hot tub was not functioning at the time. The private beach was nice but there was some smelly seaweed that was unpleasant to walk through to get to the water (were told this is common in the Keys). However, we still managed to enjoy the kayaks and paddle board that were provided. All in all, we were satisfied with the house but a little disappointed in the beach and the area in general, so if you are familiar with the Keys and are okay with small beaches, the seaweed and traffic, then this is the house for you.
Stayed 7 nights in Jun 2021
Verified

4/10 Poor

tom l.

Liked: Communication, location
Disliked: Cleanliness, listing accuracy

Great view

House needs a solid 2 weeks of upkeep
Stayed 7 nights in Mar 2021
Verified

8/10 Good

Judi H.

Liked: Check-in, communication, location, listing accuracy

Charming house

Pros: Beautiful landscape. I loved the character of the house, pool, beautiful garden and beach. There is artwork all over the house. My family enjoyed all the different kinds. As in other reviews the house needs updating. We didn’t mind that part. Con: our family used the cottage nick named “she shed” it had been closed up for awhile. It was musty and my feet we're black walking on the floor. I recommend the cleaning crew change linens and air out the place. The beds on the 3rd floor and cottage were very uncomfortable. Recommend to update queen mattress to a nice pillow top. Overall we had a fantastic trip and enjoyed the house
Stayed 7 nights in Feb 2021
Verified

10/10 Excellent

scot w.

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

This is a great family or couples rental

Great beach, excellent flats to wade toward Indian key for flyfisherman, meticulously landscaped and amazing original art. While furnishings are somewhat dated, a really aw some place!
Stayed 10 nights in Feb 2021
Verified

8/10 Good

Nathalie G.

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

Beautiful House

The house was beautiful with a private beach. I would say that the only negative thing was the rooms upstairs that didn't have a lot of air conditioning and no blinds either in the room with the double bed -
Stayed 7 nights in Dec 2020
Verified

8/10 Good

John P.

Liked: Check-in, communication, location, listing accuracy

Gorgeous property

Lots of things to do at home, bike, kayak,paddle board, pool. Surprised at the amount and terrible smell of seaweed. House was gorgeous and kitchen had everything one could need, though very poorly organized as plates, pots, ,glasses were in all different cabins. I also not very clean,we had to wash all silverware and silverware holder as there was food in it. Also food on the floor in the living room. Other than that, the location and view weee outstanding.
Stayed 8 nights in Jun 2020
Verified

10/10 Excellent

Joseph C.

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

Paradise

Beautiful house in spectacular location. Truly one-of-a-kind! House could use some basic updates (sheets, mattresses) and light maintenance but otherwise wonderful!
Stayed 8 nights in Jan 2020
Verified

8/10 Good

LJ G.

Great property and location with panoramic views of the ocean from pool and house.

Overall the property was in good condition, but needed some TLC in general maintenance and upkeep.
Stayed 7 nights in Jul 2018

About the host

Hosted by Freewheeler Vacations

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