See all properties
Entire home

Charming 2-bedroom retreat in Islamorada with stunning open water views.

Photo gallery for Charming 2-bedroom retreat in Islamorada with stunning open water views.

75130 Overseas Highway
download (1)
download (2)
download (3)
download (4)

Reviews

9.2 out of 10
Wonderful
2 bedrooms2 bathroomsSleeps 4

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 Queen Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Balcony
Separate dining area
Dining area

About this property

Charming 2-bedroom retreat in Islamorada with stunning open water views.

Enjoy peaceful Keys living at this charming bayside home located at Mile Marker 75 in Lower Matecumbe, the quiet south end of Islamorada. Set in a tranquil neighborhood, this property offers stunning sunset views and a relaxed island atmosphere perfect for a laid-back getaway.

Out back, you'll find a small private beach area surrounded by palm trees, creating a secluded space to unwind and enjoy the bay. The screened porch is the perfect place to take in the colorful evening sunsets, complete with comfortable tables and chairs for outdoor dining or relaxing.

For even better views, head up to the roof deck where you can take in panoramic sights of both the bay and ocean sides of the island.

Inside, the home features a comfortable layout with bedrooms located on opposite sides of the house and the living and common areas in between—offering both privacy and space to gather. Amenities include a flat-screen TV in the living room, cable television, and Wi-Fi.

While dockage is not available at this property, Anne's Beach is located just down the road. This beautiful natural area offers boardwalk trails, picnic and BBQ spots, and sandy areas tucked within the mangroves—perfect for a day by the water.

Vacation Rental License: VR-041

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. Reservations are not confirmed until you speak directly 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.

Add dates for prices

Have a question?

AI iconBeta

Get instant answers with AI powered search of property information and reviews.

Similar properties

106 Anglers Way
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!
  • Pool
  • Kitchen
  • Washing machine
  • Dryer
10.0 out of 10, Exceptional, (119 reviews)
Serenity by the Sea!! Anglers Reef with Boat Slip Available!!

House Rules

Check in after 3:00 PM
Minimum age to rent: 22
Check out before 10:00 AM
default

Children

Adults only
default

Events

No events allowed
default

Pets

Pets allowed
default

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 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. Robbie’s of Islamorada and Bud n' Mary's Dive Center are worth checking out if an activity is on the agenda, while those wishing to experience the area's natural beauty can explore San Pedro Underwater Archaeological Preserve State Park and Indian Key Historic State Park. With scuba diving, snorkelling and fishing nearby, you'll find plenty of adventures in the water.
View more Holiday homes in IslamoradaOpens in a new window
Map
Islamorada, FL

What's nearby

  • Sunset Drive Beach - 18 min walk - 1.5 km
  • Anne's Beach - 2 min drive - 3.3 km
  • Robbie’s of Islamorada - 4 min drive - 4.3 km
  • Bud n' Mary's Dive Center - 8 min drive - 9.3 km
  • Florida Keys Brewing Co. - 11 min drive - 12.6 km

Getting around

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

Restaurants

  • ‪Hungry Tarpon Restaurant - ‬3 min drive
  • ‪Lazy Days Restaurant - ‬6 min drive
  • ‪Papa Joe’s Waterfront - ‬6 min drive
  • ‪Islamorada Fish Company - ‬8 min drive
  • ‪Tiki Bar at Amara Cay Resort - ‬6 min drive

Frequently asked questions

Is Charming 2-bedroom retreat in Islamorada with stunning open water views. pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Charming 2-bedroom retreat in Islamorada with stunning open water views.?

As of 26 Mar, 2026, prices found for a 1-night stay for 2 adults at Charming 2-bedroom retreat in Islamorada with stunning open water views. on 12 May, 2026 start from S$463, 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.

What time is check-in at Charming 2-bedroom retreat in Islamorada with stunning open water views.?

Check-in begins at 3:00 PM.

What time is check-out at Charming 2-bedroom retreat in Islamorada with stunning open water views.?

Checkout is at 10:00 AM.

Where is Charming 2-bedroom retreat in Islamorada with stunning open water views. located?

Located in Matecumbe, this holiday home is within 2 miles (3 km) of Sunset Drive Beach, San Pedro Underwater Archaeological Preserve State Park and Anne's Beach. Robbie’s of Islamorada and Indian Key Historic State Park are also within 3 miles (5 km).

Reviews

9.2

Wonderful

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. 13 out of 17 reviews
Rating 8 - Good. 3 out of 17 reviews
Rating 6 - Okay. 0 out of 17 reviews
Rating 4 - Poor. 0 out of 17 reviews
Rating 2 - Terrible. 1 out of 17 reviews

8.8/10

Cleanliness

10/10

Check-in

9.0/10

Communication

10/10

Location

9.2/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Shannon C.

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

Great view!

Love the privacy of the beach.
Stayed 7 nights in Sep 2024
Verified

10/10 Excellent

Dave S.

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

Total Comfort

Extremely well equipped complete with great views from either the veranda or the small, private beach. Close to everything you need. Would return in a heartbeat.
Stayed 8 nights in Dec 2020
Verified

8/10 Good

Loralee S.

very nice

Our 2nd visit to this property. It is a comfortable spot, just not walking distance to much of anything...Also, would be nice if the roof offered a hot tub ...just a thought. Also it is inconsistent on "water toys"...They should be available or not available. Last year we had access, this year not and no one could tell us where the key was to access....this posed some problems. House is not fancy, but clean and friendly.
Stayed 7 nights in Nov 2018
Verified

2/10 Terrible

Ryan M.

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

Bait and switch

First let me start by saying that the location on the beach is absolutely amazing. That’s where the positives end. When we arrived at the property we noticed it looked a bit disheveled. Bags of construction sand lying on the beach, trash/empty water bottles and beer bottles strewn about the beach area and yard, multiple garden hoses thrown all over the property, construction materials and debris left on the property including a large ladder and items that appear to have been left out for months or years. The home itself needs some major work. It was built in 1993 and honestly it probably hasn’t had anything done to it since then. The screen doors had holes, the only portion of the entryway that locks is the deadbolt at the handle is broken and just pushes open. The bannisters going up the staircase are loose and Jerry rigged with rand lumber. Once inside the unit it’s very dated. Think 1993 design. The couches are very uncomfortable, the home is cluttered and the TV didn’t work. The coffee table collapsed as I placed a drink on it. It’s clearly been repaired in the past as evidenced by duct tape. The bathroom had what appeared to be a smashed roach in the corner and the towels and wash cloths were a hodgepodge of worn out multi colored towels with tears and tears of use under their belt. Moving onto the bedrooms, the beds were so hard and uncomfortable I checked to make sure it wasn’t two box springs stacked together. The pillows are so flat and cheap/worn out it takes 4 to equal one normal pillow. The roof leaks, I mean pours water when it rains and has been as evidenced by the large water staining on the ceiling. Truth be told I tried to book somewhere else and ask for a refund but couldn’t find anything within reason that wasn’t owned by FreeWheeler. We ended up checking out a day early because the unit became unusable due to the water leak from the ceiling. When I brought the issues to the attention of Crystal who seems to be the property manager she offered nothing but “Sorry, we’ll get it fixed.” I asked if she had every been to the home, she stated she hadn’t. It’s completely evident they purchased a furnished home from someone and threw it onto VRVO. There are picture frames with children on the night stands and personal effects form the family that previously owned the property all over the home. I had high hopes after looking at the pictures. It all I got was a let down with a beautiful view.
Stayed 7 nights in Nov 2022
Verified

10/10 Excellent

Debbie T.

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

Great place

We love the property
Stayed 7 nights in May 2022
Verified

10/10 Excellent

Maureen M.

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

keys vacation

outstanding property !
Stayed 14 nights in May 2022
Verified

10/10 Excellent

tonya g.

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

Paradise

Outdoor space was beyond my expectations. Inside there is a lot of stuff and I think that impacts the cleanliness and ease of keeping it clean. Either way it was a fantastic place and the price was very good. For the price and the outdoor space including a wonderful screened porch I would easily recommend it. Just bring your own coffee maker and it might be a good idea to bring your own linens, pillows, and a mattress topper.
Stayed 7 nights in Dec 2021
Verified

10/10 Excellent

Debbie T.

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

Great beach house was cool. Rooftop awesome beds very hard

Easy
Stayed 7 nights in Oct 2021
Verified

10/10 Excellent

Bonnie s.

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

Beach bungalo

2nd time at this property and it was better than the first time
Stayed 7 nights in Oct 2021
Verified

8/10 Good

kent c.

Liked: Cleanliness, check-in, communication, location

See below

Concerns were verbally relayed to Freewheeler and they appreciated comments. Overall very relaxing and enjoyable. Main concern were some inaccuracies in the rental paperwork. WiFi code and no mention of construction occurring Nextdoor.
Stayed 8 nights in Apr 2021
Verified

10/10 Excellent

Maureen M.

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

keys vacation

Outstanding property !
Stayed 7 nights in Apr 2021
Verified

10/10 Excellent

Elizabeth E.

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

Best honeymoon house on the island

We got to meet the owner and she was extremely nice and accommodating. The house is gorgeous and has a homey feel to it. We had a blast taking finding and relaxing on the rooftop terrace. The privacy of the small beach was perfect. We left the doors open and listened the waves- because the screen porch kept all unwanted guests away. I recommend the November trip. The house is more than big enough for two couples. We would stay again tomorrow. Islamorada was more fun than key west to us. But the drive to key west is not bad and keeps you out of hoopla. Definitely booking again!
Stayed 7 nights in Nov 2020
Verified

10/10 Excellent

Gary R.

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

Perfect house and location

We had a blessed time lots of relaxing. House is better than the photos loved the screened balcony. The home was super clean appliances are dated but everything works as it should. Very quiet neighborhood could not have ask for a better week. Crystal was great, getting keys is a breeze. Thanks to everyone at Freewheeler Vacations
Stayed 7 nights in Dec 2020
Verified

10/10 Excellent

Geoffrey C.

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

Perfect vacation

Location on the Florida Bay wS perfect. Excellent house for kids. Tile floors were no worry, low maintenance. My only complaints would be quality of sheets and the mosquitoes when the breeze wasn’t blowing. Screened porch was awesome.
Stayed 7 nights in Oct 2020
Verified

10/10 Excellent

Nicole M.

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

Great location and privacy

The house is great- the privacy and private beach were exactly what we were looking for.
Stayed 14 nights in Mar 2020
Verified

10/10 Excellent

Jen H.

LOVED EVERYTHING!

It was so relaxing being right on the water. We had everything we needed! The house was really comfortable and sitting on the screened porch looking at the water with a coffee or a cocktail was a highlight! Great house and location for kids. Thanks for a great vacation.
Stayed 7 nights in Apr 2018
Archival

8/10 Good

Loralee S.

Nice and quiet

Property was cute with lovely ocean views. Very quiet there. Everything is 10-15 minutes from the property. Groceries are 15-20 + drive. Place was nice for a lazy sort of vacation. We enjoyed renting kayaks and paddle boards for daytime fun. The yard is small and after Irma, there is no "beach" as it once had, but we dealt with it. Lots of Iguanas on the property which were fun to watch from the balcony.We would return for a laid back vacation.
Stayed 7 nights in Oct 2017

About the host

Hosted by Freewheeler Vacations

Host profile image

Languages:

English

Premier Host

They consistently provide great experiences for their guests
Tell us how we can improve our siteShare feedback