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

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A spacious living area with a wooden ceiling, a bar with stools, and a large window offering a view of palm trees and the ocean.
A kitchen with wooden beams, a bar area with stools, and a dining area with a bed and window.
A waterfront property with multiple houses, a dock, and a swimming pool.
A bedroom with a large bed, a TV, a fireplace, and a balcony with a view of the ocean.
A modern kitchen with white cabinetry, granite countertops, and a central island.

Reviews

10 out of 10, Loved by Guests
Top 10% of guest reviews in this area

Highlights

  • Family fun awaits

    Top-rated for families.

  • Beach equipment

    A rare find — beach equipment ready to go for your days by the sea.

  • Centrally-located

    You're never far from where you need to be with this convenient location.

  • Discover nearby landmarks

    Walk to Islamorada Brewery & Distillery
5 bedrooms3 bathroomsSleeps 10

Popular amenities

  • Balcony
  • Spa pool on site
  • Private pool
  • Outdoor barbecue
  • Air-conditioning
  • Refrigerator

Explore the area

View map
Islamorada, FL
  • Place, Islamorada Brewery & Distillery
    ‪7 min walk‬
  • Place, History of Diving Museum
    ‪10 min walk‬
  • Place, Lorelei Restaurant & Cabana Bar
    ‪16 min walk‬
  • Airport, Marathon, FL (MTH-Florida Keys Marathon)
    ‪47 min drive‬

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.

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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

Property # 189714vb
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
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

Located in Matecumbe, a neighbourhood in Islamorada, this holiday 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. Consider Lorelei Restaurant & Cabana Bar for a night out or MoradaWay Arts & Cultural District if you're travelling with kids. Discover the area's water adventures with jet skiing and kayaking nearby, or enjoy the great outdoors with cycling and ecotours.
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Map
Islamorada, FL

What's nearby

  • Islamorada Brewery & Distillery - 7 min walk - 0.7 km
  • History of Diving Museum - 10 min walk - 0.9 km
  • beach near Islamorada - 12 min walk - 1.1 km
  • Lorelei Restaurant & Cabana Bar - 16 min walk - 1.4 km
  • Florida Keys Brewing Co. - 2 min drive - 2.3 km

Getting around

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

Restaurants

  • ‪Lorelei Restaurant & Cabana Bar - ‬15 min walk
  • ‪Wahoo's Bar & Grill - ‬2 min drive
  • ‪Wendy's - ‬11 min walk
  • ‪Islamorada Fish Company - ‬3 min drive
  • ‪Starbucks - ‬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 19 September 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 3 October 2026 start from NZ$16,936, 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 at Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!?

On-site 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!?

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. 91 out of 92 reviews
Rating 8 - Good. 1 out of 92 reviews
Rating 6 - Okay. 0 out of 92 reviews
Rating 4 - Poor. 0 out of 92 reviews
Rating 2 - Terrible. 0 out of 92 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Wonderful property!!!
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We loved the layout and location of the house! It was perfect for our family vacation of 8. There was plenty of space! The pool and dock was private and lively.
Stayed 7 nights in May 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
Judy was a great hostess- great communication. The house is amazing- has a cool old school Florida vibe, is very well stocked. We loved fishing off the dock and watching the sunset. The grounds are beautiful and the location is great. Check out the Dolphin Life Hospital next door and its sister location in Key Largo (there you can see/interact with Dolphin). The Bayside Gourmet just to the left is a funky 80’s esque restaurant with fabulous Italian food and pizza. I wish we had rented kayaks for the week as it would be easy to kayak there. The place next door had some kayaks. Would definitely stay again!
Stayed 7 nights in Jul 2026
Response from VrboOwner on 25 July 2026
Thank you Kristin for your great review! Your description of our home and the property is superb. So thrilled you enjoyed the dock and our gorgeous sunsets. We strive to have a well stocked home from "starter packs" of basic essentials to gourmet kitchen utensils and cooking items. Also, BBQ "stuff" for the outdoor chef. So glad that you discovered Bayside Gourmet next door-a hidden gem! Thanks again for your visit to our Island Paradise. We would love to welcome you back again in the future. Warm Wishes, Judy & Ken
Verified review

10/10 Excellent

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
Response from VrboOwner on 16 March 2026
Thank you so much for the kind words! We’re so glad your family enjoyed the stay and were able to take advantage of the pool, dock, and waterfront views. It means a lot to hear the house had everything you needed and that everyone was comfortable. We’d love to host you again anytime.
Verified review

10/10 Excellent

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
Response from VrboOwner on 23 February 2026
Good morning John, So thrilled that you had a wonderful stay here at Osprey Bay Villa! The spectacular sunsets and heated pool never disappoint. You and your family were great guests. It will be excellent if and when you return again to our "Island in the Sun" Hope to see you soon, Judy Moeller and crew
Verified review

10/10 Excellent

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 review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay at Osprey Bay Villa in Islamorada from February 4th–11th. The villa was clean, comfortable, and in a perfect location for enjoying the Keys.We especially loved the pool and hot tub — both were spotless and so relaxing. The sunsets were absolutely beautiful and made each evening feel special. The property had everything we needed and felt like a true home away from home....but with better weather and views!!!!Host Judy was wonderful and very responsive.We would definitely stay here again and highly recommend it for a relaxing Islamorada getaway.
Beautiful sunsets every night!
Stayed 7 nights in Feb 2026
Verified review

10/10 Excellent

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

10/10 Excellent

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
Response from VrboOwner on 19 August 2025
Thank you William for your visit here to Osprey Bay Villa! So glad you could enjoy all the amenities that the property, house and pool has to offer. It was a pleasure having you and your crew down here in Islamorada, our Island in the Sun🏝🌅🐬 We look forward to your future return visit!! Judy and Ken
Verified review

10/10 Excellent

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
Response from VrboOwner on 1 December 2025
Thank you so much for the wonderful review! We’re thrilled to hear your group had plenty of space and enjoyed the dock — the variety of fish you spotted is incredible! It’s always fun to hear what guests see right from the backyard. We’re glad the home worked well for you and that the beds were comfortable for everyone. It means a lot that you chose to spend your trip with us, and we hope we’ll have the chance to welcome you back to Osprey Bay Villa again soon.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 20 July 2025
Thank you so much for the kind words! We’re so glad you had a wonderful week and felt right at home at Osprey Bay Villa. It means a lot to hear the house and location worked out perfectly for your trip—and we truly appreciate the recommendation! We'd love to have you back anytime 🌴 Warm regards, Judy
Verified review

10/10 Excellent

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
Response from VrboOwner on 25 July 2020
Thank you Aaron for your visit and nice words:-) We are honored to have your 1st visit to Islamorada in the Florida Keys to be our property, Osprey Bay Villa. We will gladly welcome you back for a second time and more in the future. The manatee and parrot fish at the dock will be here waiting for you and your friends. Take care, Judy & Ken
Verified review

10/10 Excellent

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
Response from VrboOwner on 29 March 2020
Thank you for the nice review. Yes, the sunsets, fishing and water access are fabulous! Thrilled you will be returning next year!
Verified review

10/10 Excellent

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
Response from VrboOwner on 29 March 2020
Thank you for the caring.
Verified review

10/10 Excellent

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 review

10/10 Excellent

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

Paradise

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

10/10 Excellent

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
Response from VrboOwner on 29 March 2020
Yes, the sunsets in Islamorada and particularly from the decks of Osprey Bay Villa never cease to amaze all! Thank you for your visit. J & K
Verified review

10/10 Excellent

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
Response from VrboOwner on 10 September 2024
Thank you Edward for your great review! The pool, dock and Florida Keys warmer waters are beckoning you to come back;-)) Osprey Bay would love to host you and your crew for any future vacation visit! Warmest Wishes, Judy & Ken
Verified review

10/10 Excellent

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 review

10/10 Excellent

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
Response from VrboOwner on 25 January 2021
Thank you Brian and crew for your return visit! You were great guests. Hope to see you in the future! Warmest Regards, Judy
Verified review

10/10 Excellent

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
Response from VrboOwner on 11 August 2025
Thank you so much! So glad Osprey Bay Villa was the perfect fit for your group. We love to hear about all the wildlife you spotted right from the dock! Please come back anytime for more sunsets, relaxation, and time on the water.
Verified review

10/10 Excellent

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
Response from VrboOwner on 20 July 2025
Thank you so much, John! We're thrilled to hear that Osprey Bay Villa had everything you needed for a perfect stay—and that you got to enjoy some incredible wildlife sightings right off the dock! 🐠🌅 It means a lot to know the location, sunsets, and communication all hit the mark. We'd love to welcome you back anytime for that longer stay! Warmly, Judy
Verified review

10/10 Excellent

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

About the host

Hosted by Judy Moeller

Host profile image

Why they chose this property

What makes this property unique

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English

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