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

Waterfront holiday home with water park and Hot tub

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

Pool
Outdoor dining
Living area
Room
Terrace/patio

Reviews

10 out of 10
Exceptional
5 bedrooms3 bathroomsSleeps 10488.2 sq m

Popular amenities

  • Parking available
  • Dryer
  • Air conditioning
  • Washer

Explore the area

View map
Islamorada, FL
  • Place, Islamorada Brewery & Distillery
    ‪6 min walk‬
  • Place, Florida Keys Brewing Co.
    ‪3 min drive‬
  • Place, Theater of the Sea
    ‪5 min drive‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)

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.

Add dates for prices

Amenities

Pool
Hot tub
Kitchen
Washing machine
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher, a first aid kit and a deadlock

We should mention

This property does not have any lifts
A car is required for transport to and from this property

About the area

Islamorada

Located on the waterfront, this holiday home is in Matecumbe, a neighbourhood in Islamorada. Hurricane Monument and Indian Key Historic State Park are local landmarks, and the area's natural beauty can be seen at Windley Key Fossil Reef Geological State Park and San Pedro Underwater Archaeological Preserve State Park. Make sure you get close to 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
  • Florida Keys Brewing Co. - 3 min drive - 2.3 km
  • Theater of the Sea - 5 min drive - 4.6 km
  • Bud n' Mary's Dive Center - 8 min drive - 5.7 km

Getting around

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

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬15 min walk
  • ‪Wendy's - ‬11 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪The Trading Post - ‬18 min walk
  • ‪Whale Harbor Buffet - ‬2 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.

Is Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! pet-friendly?

No, pets are not allowed at this 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!?

Checkout 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 holiday 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 mile (2 km).

Reviews

10

Exceptional

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. 78 out of 79 reviews
Rating 8 - Good. 1 out of 79 reviews
Rating 6 - Okay. 0 out of 79 reviews
Rating 4 - Poor. 0 out of 79 reviews
Rating 2 - Terrible. 0 out of 79 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

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

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

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

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

10/10 Excellent

Jim A., Charleston, SC

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

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

10/10 Excellent

Julie C.

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

love

The ocean is awesome!!!
Stayed 7 nights in Nov 2021

10/10 Excellent

Susu D.

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

Parents with married children

We loved Osprey Villa! We were a party of 6. Parents, and 2 children/couples. (20s) Tne house was spacious! We all had our privacy and the common areas were great! The kitchen was super well stocked! Pool with floats! The dock was beautifully and protected for our 24’ CC. Judy was so easy to deal with! We will definitely be back!
Stayed 7 nights in Jul 2023

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

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

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

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

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

10/10 Excellent

Shannon S.

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

Islamorada Thanksgiving

My family of 10 stayed at this property the week of Thanksgiving. This property was AMAZING! We loved it. The owners of this property have thought of everything, ie, 2 kitchen sinks, 2 ovens, 2 washers, 3 dryers. Lots of room for the family, we were treated to stunning sunsets daily, we brought our boat, went fishing, explored the area restaurants. The pool area was spacious and gorgeous. We loved this property and hope to some day get to stay here again in the future! to to stunning sunsets
Stayed 7 nights in Nov 2024

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

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

10/10 Excellent

Lori H.

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

Howell

It was a wonderful week. Home was fabulous and very clean. Great area near everything! Pool and jacuzzi were on point. Judy was very helpful with my booking. Definitely recommend staying here! Worth every penny! Thank you for sharing your home!
Stayed 7 nights in Feb 2024

10/10 Excellent

colleen c.

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

Family getaway

We had an amazing time! The house is spacious, and perfect for a family! We had 2 toddlers and they graciously put the safety gate up around the pool! The views are unbelievable. We rented paddle boards and kayaks for the week that were delivered to the home. The beach area is a perfect spot to take off for a quick swim, snorkel, or ride. Would definitely come back.
Stayed 7 nights in Jan 2024

10/10 Excellent

Jeff S.

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

Winter Break

Host was amazing and easy to communicate with. Very clean property. House was well stocked with everything you may need. Pool and shot tub were awesome for the kids. Dock and Bay Area were amazing. Would absolutely recommend.
Stayed 7 nights in Jan 2024

10/10 Excellent

Laura K., NC, USA

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

Amazing property

This is a beautiful home in a perfect location. The interior is cozy, kitchen has all you need, heated pool is perfect for the cooler Keys days that we had. Judy was super responsive to all questions. We really enjoyed kayaking on the bay and cooking in so we could dine looking out over the beautiful landscape! Would love to return one day!
Stayed 7 nights in Dec 2023

10/10 Excellent

Andrew C., USA

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

10/10 Excellent

Linda C.

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

Great rental property

This property was very well appointed-little things like paper products, coffee, spices that make a stay easier. Large kitchen for preparing meals,spacious common areas. Grounds were neat and tidy. Landlord was accommodating and available. Already booked for next year.
Stayed 7 nights in Mar 2023

10/10 Excellent

Luke B.

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

Paradise

Clean quiet and tranquil.
Stayed 7 nights in Feb 2023

10/10 Excellent

ken M.

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

Absolutely Outstanding

This was our first family vacation since covid changed everything and we had an outstanding experience. The pool was really big and warm, the hot tub was a great option, and the place was equipped better than anywhere we have stayed. We rented a boat from A1A and used the dock at the house. We went out to the sandbar in front of the Post Card Inn and had a blast. We had nine people in the unit and we NEVER felt crowded or cramped. The kitchen was so well equipped with everything we could have asked for. The furniture could use some updating but I wouldn't let that sway you away from this place. Overall, 5 stars and an outstanding experience.
Stayed 7 nights in Dec 2022

10/10 Excellent

Kristin B.

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

Perfect vacation!

There were 10 of us (8 adults & 2 children) who stayed at Osprey Bay during the week of Thanksgiving. The house was better than in the pictures. Before we arrived I was worried about having having 5 bedrooms and 3 baths. But it wasn’t an issue at all. We were rarely inside. We were in the heated pool, hot tub or snorkeling off the dock most of the time. We saw so many varieties of colorful fish, octopus , sharks, and a huge hermit crab right off the dock! We rented a hurricane boat through A1A water sports . We planned to use it every day to go to the reef and snorkel. We actually went 2 times but we saw more fish by the dock at the house. So we used the boat to explore the area, the islands and look at the huge houses nearby. We all like to cook so we made a lot of meals. The kitchen looked newly remodeled. It had everything we needed and more! Everyone wanted fresh seafood with every dinner we ate at the house so we went to Lobster Walk to buy fresh seafood several times. We ate at Robbie’s, Lazy Days, Lor-e-Lei, and Islamorada Brewery. We liked them all. We went to Theater of the Seas. If you go make sure you do “meet the sea lion” program. It was our favorite. We do a family vacation every 2 years. We’ve gone to outer banks, Mexico, Honduras, and Belize. Everyone said this was our best trip. It was because of the house, grounds, location, and amenities. We loved the beachy vibe of the house and loved how comfortable it was. There was plenty of room for all 10 of us. The Florida Keyes are beautiful and there so much to do and see. We hope to be back in 2024!
Stayed 7 nights in Nov 2022

About the host

Hosted by Judy Moeller

Host profile image

Why they chose this property

What makes this property unique

Languages:

English
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