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Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

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Pool
Outdoor dining
Living area
Room
Terrace/patio

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area
5 bedrooms3 bathroomsSleeps 105255 sq ft

Popular amenities

  • Ocean view
  • Kitchen
  • Washer
  • Dryer

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

1 King Bed

Bedroom 2

1 King Bed

Bedroom 3

2 Double Beds

Bedroom 4

1 Queen Bed

Bedroom 5

2 Double Beds

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

Deck or patio
Porch or lanai
Kitchen
Balcony
Outdoor play area
Garden
Dining area

About this property

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

OSPREY BAY VILLA – Your private bayfront escape in the heart of Islamorada, Florida Keys!

Relax and enjoy incredible panoramic bay and sunset views from this elegant yet casual "Old Keys Charm" home, designed for the perfect family or group getaway. With a heated pool, hot tub, and deep-water dock, you’ll experience the best of island living—whether you’re soaking up the sun, exploring by boat, or strolling to local restaurants and shops.

KEY FEATURES:

*5 bedrooms, sleeps 10–12 guests
- 2 king bedrooms (including master suite)
- 1 queen bedroom
- 2 bedrooms with 2 queen beds
* 3 full bathrooms
- Master bath with separate vanity room
- Full bath with bathtub + separate shower, double sinks
- Pool-level bath with shower + direct outdoor access
* Fully equipped gourmet kitchen with open dining room and atrium garden
* Spacious living room with coral rock fireplace + wet bar
* Second-level master suite with private bayfront veranda + fireplace
* Multiple sunning decks, heated pool, and hot tub
* Deep-water dock + boat basin (perfect for boating, snorkeling, kayaking & paddleboarding)
* Lush tropical landscaping + private sandy beach area for wading
* Incredible sunset views from expansive waterfront lawn and outdoor spaces
* Secluded yet walkable to iconic Islamorada restaurants and local shops

Come, Relax & Enjoy!
Your perfect Florida Keys vacation awaits.
Our prices include all fees. No hidden fees.

Add dates for prices

Amenities

Pool
Hot Tub
Kitchen
Washer
Dryer
Free WiFi

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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

Children allowed: ages 0-17
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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
No Jet Skis, Wave Runners, or Ultra Light Gliders are Allowed. No RV's and/or Motor Homes are Allowed.
Property must be booked Saturday to Saturday for a minimum of 7 nights, otherwise we cannot accept the booking.

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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit, and a deadbolt lock

We should mention

This property does not have elevators
A car is required for transportation to and from this property

About the neighborhood

Islamorada

Located in Matecumbe, a neighborhood in Islamorada, this vacation home is near a water park and on the waterfront. History of Diving Museum and Keys History & Discovery Center are cultural highlights, and some of the area's landmarks include Hurricane Monument and Indian Key Historic State Park. Be sure to check out the area's animals with activities such as game walks and birdwatching.
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Map
Islamorada, FL

What's nearby

  • Islamorada Brewery & Distillery - 6 min walk - 0.6 km
  • History of Diving Museum - 10 min walk - 0.9 km
  • Keys History & Discovery Center - 12 min walk - 1.1 km
  • Florida Keys Brewing Co. - 2 min drive - 2.3 km
  • MoradaWay Arts & Cultural District - 2 min drive - 2.4 km

Getting around

  • Marathon, FL (MTH-Florida Keys Marathon) - 40 min drive

Restaurants

  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Lorelei Restaurant & Cabana Bar - ‬15 min walk
  • ‪Wendy's - ‬11 min walk
  • ‪Bayside Gourmet of Islamorada - ‬3 min walk
  • ‪Islamorada Fish Company - ‬3 min drive

Frequently asked questions

Does Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! have a pool?

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

How much does it cost to stay at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

As of Mar 26, 2026, prices found for a 1-night stay for 2 adults at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! on May 2, 2026 start from $1,286, 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 Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! pet-friendly?

No, pets are not allowed at this property.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

Check-in begins at 4:00 PM.

What time is check-out at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

Check-out is at 10:00 AM.

Where is Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! located?

This family-friendly Islamorada vacation home is located on the waterfront, within a 10-minute walk of History of Diving Museum and Islamorada Brewery & Distillery. Keys History & Discovery Center and Matecumbe United Methodist Church are also within 1 mi (2 km).

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 83 out of 84 reviews
Rating 8 - Good. 1 out of 84 reviews
Rating 6 - Okay. 0 out of 84 reviews
Rating 4 - Poor. 0 out of 84 reviews
Rating 2 - Terrible. 0 out of 84 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Chris P.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything was wonderful! Our family really enjoyed our stay. The house is very well equipped with everything you need. The beds are comfortable, the pool is huge, the waterfront view is amazing and the dock on the water was really nice.
Stayed 7 nights in Mar 2026
Verified

10/10 Excellent

John C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. All is as described. Host is responsive and quick with communication. Will stay again
Stayed 7 nights in Feb 2026
Verified

10/10 Excellent

Allison S.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was great and very responsive. House was wonderful charming and had everything we needed.
Stayed 7 nights in Jan 2026
Verified

10/10 Excellent

Charles M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Excellent! Plenty of room for 9 people. Dock for fishing was amazing. We saw shark, grouper, moray eel, barracuda, clown fish, and more all from the dock. Overall, great place to stay with family, friends, or both. Beds in every room were very comfortable!!
Stayed 7 nights in Nov 2025
Verified

10/10 Excellent

william c.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great time. House is great with all the amenities and fantastic views. Look forward to coming back for sure
Stayed 7 nights in Aug 2025
Verified

10/10 Excellent

George C.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Property was very nice and well appointed.
Stayed 7 nights in May 2025
Verified

10/10 Excellent

Phil T.

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

Return Guests - As good as last time

Excellent family holiday once again. Couldn’t ask for anything more, great accommodation, great location and great fishing what more can you want.
Stayed 7 nights in Oct 2024
Verified

10/10 Excellent

Andrew C.

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

Great place to stay

House has it all. Great location, great host, everything was wonderful.
Stayed 7 nights in Nov 2023
Verified

10/10 Excellent

kathryn u.

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

Great house

We had a wonderful week in Islamorada in Osprey bay villa. Great, large very comfortable and accommodating home with all amenities. And great location in the middle of everything!Highly recommend staying here. Just was a great host and very responsive if needed
Stayed 7 nights in Mar 2025
Verified

10/10 Excellent

donald n.

Liked: Cleanliness, check-in, communication, location, listing accuracy
Everything about the property was great. Super location. Comfortably accommodated all ten of us. We fished on the pier everyday and moored our boat by the dock. We saw dolphins, manatees, sharks and plenty of fish from the pier. We spent hours in the pool just soaking. Plenty of nearby places to jog or walk. The kitchen had every utensil imaginable. It was sad to have to leave.
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

John K.

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

Beautiful House

Perfect house, had every single thing you could want or need...it left us wanting nothing other than a longer stay! Saw a manatee, stingray, barracuda and nurse sharks off the dock with plenty of fish to be caught. Beautiful sunsets every single night. Great location with plenty to do in Islamorada. Judy was very prompt in her communications. Thank you!
Stayed 7 nights in Jul 2025
Verified

10/10 Excellent

Jeff S.

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

Great week

Great property! Spent with my wife, children and grandchildren. We all enjoyed the pool and hot tub. Great access on the dock for fishing or just taking in the view. Would highly recommend. Great host she is a pleasure to work with.
Stayed 7 nights in Jan 2025
Verified

10/10 Excellent

Aaron G.

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

Lovely house close to it all but quietly tucked away

Amazing house with views for days! Very clean and the owner was always quick to respond. Will definitely stay here again next time we are in the keys.
Stayed 7 nights in Jul 2020
Verified

10/10 Excellent

Judy M.

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

Beautiful home and entire property. .

Loved the fish at the dock and the great access to the ocean and/or the bay. Most glorious serene sunsets from the decks.
Stayed 7 nights in Jun 2019
Verified

10/10 Excellent

Judy M.

An Island Paradise!

Lovely home with love and warmth of family and friends. Not to mention the Spectacular Sunsets!
Stayed 4 nights in Oct 2018
Verified

10/10 Excellent

Edward M.

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

Review

Excellent place. Would definitely return. Just was very attentive to all our needs
Stayed 7 nights in Aug 2024
Verified

10/10 Excellent

Laurie B.

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

Excellent accommodations and location, host went above and beyond to make a great experience.

Very satisfied with the property and access to all Islamorada has to offer. Property is exactly as pictured and described on the vrbo site. Host was great with communication and hospitality. Would book again
Stayed 7 nights in Jan 2022
Verified

10/10 Excellent

Luke B.

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

Paradise

Clean quiet and tranquil.
Stayed 7 nights in Feb 2023
Verified

10/10 Excellent

Janna S.

Loved the house!

House, pool, and hot tub were perfect for our extended family vacation! Everyone could gather together or have time away if they needed a break! The pool was the favorite part of the trip for the kids!
Stayed 7 nights in Dec 2018
Verified

10/10 Excellent

Mary O.

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

Fantastic week- love

Wow-we’ve rented several houses over the years in Islamorada and this was by far THE BEST!! We all loved the heated pool, the dock, decking and the privacy!! The house is well stocked and the kitchen set up is amazing. Everyone wants to come back!! Thank you for sharing your beautiful home with us
Stayed 7 nights in Dec 2024
Verified

10/10 Excellent

Judy M.

Excellent!

Thoroughly enjoyed the home with the wonderful pool, dock, flora and fauna. The sunsets were stunning. Hope to return again.
Stayed 7 nights in Mar 2019
Verified

10/10 Excellent

Matt U.

Great location

Great host, house and location. Dock in backyard worked great for 27' boat. Easy access to the ocean. Great sunsets from the deck. Will be back!
Stayed 7 nights in Jun 2018
Verified

10/10 Excellent

Jim A.

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

Osprey Bay Villa

Beautiful property! Amazing view. Very nice dock and pool. Centrally located to everything in Islamorada. Judy was very helpful with check-in and couldn’t have been more accommodating. Highly recommend Osprey Bay Villa!
Stayed 14 nights in Dec 2021
Verified

10/10 Excellent

Brian B.

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

Excellent

This is our second time staying at this property and we love it. The listing is accurate and the owner is very helpful. Thank You!
Stayed 7 nights in Jan 2021
Verified

10/10 Excellent

Sharman U.

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

Amazing house and stay in Islamorada!

We had a fantastic week at Osprey Bay. The house and grounds are just perfect for a relaxing but active getaway. There was plenty of room for our group of 9 and the house was well appointed with everything we needed. We also appreciated Judy's great communication. We are looking for another date to come back and stay!
Stayed 7 nights in Sep 2020

About the host

Hosted by Judy Moeller

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Why they chose this property

What makes this property unique

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