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.

A two-story house with a tiled roof, white walls, and a covered porch with arches.
A rooftop terrace with a view of the sea and trees.
A kitchen with a blue countertop, wicker chairs, and wooden cabinets.
A spacious living area with a tiled floor, a dining table with chairs, a sofa, a ceiling fan, and a large window allowing natural light.
A bedroom with a bed, a nightstand, a lamp, a vase with flowers, and a window with blinds.

Reviews

9.2 out of 10
Wonderful

Highlights

  • Top rated beach location
    Discover paradise at this top rated beach location.
  • Discover nearby landmarks
    Close to Sunset Drive Beach
Sleeps 42 bedrooms2 beds

Popular amenities

  • Dog-friendly
  • Kitchen
  • Washing machine
  • Air-conditioning
  • Barbecue
  • Balcony

Explore the area

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

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.

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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

Pets allowed: dogs less than 23 kg per pet (limit one pet total)
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Smoking

Smoking is not permitted

Important information

You need to know

Property # 4555893
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. Ready for a night out? Consider Lorelei Restaurant & Cabana Bar and Hog Heaven. With scuba diving, snorkelling and fishing nearby, you'll find plenty of adventures in the water.
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 - 4.7 km
  • Bud n' Mary's Dive Center - 8 min drive - 9.6 km
  • Islamorada Brewery & Distillery - 11 min drive - 14.6 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
  • ‪Islamorada Fish Company - ‬8 min drive
  • ‪Papa Joe’s Waterfront - ‬6 min drive
  • ‪Midway Cafe & Coffee Bar - ‬7 min drive

Frequently asked questions

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

Yes, this property allows dogs (limit 1 total) with a maximum weight of up to 23 kg per pet.

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

As of 20 Aug 2026, prices found for a 1-night stay for 2 adults at Charming 2-bedroom retreat in Islamorada with stunning open water views. on 7 Sept 2026 start from AU$4,175, 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).

About the host

Hosted by Freewheeler Vacations

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Languages:

English

Premier Host

They consistently provide great experiences for their guests
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