Entire home

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

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3 bathroomsSleeps 105255 sq ft

Popular amenities

Parking available
Pool
Dryer
Hot tub
Air conditioning
Washer

Explore the area

Islamorada, FL

Islamorada Brewery & Distillery
‪6 min walk‬
Florida Keys Brewing Co.
‪2 min drive‬
Theater of the Sea
‪4 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪52 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.

Property manager

Judy Moeller

Languages

English

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washing machine

Dryer

Free WiFi

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Kitchen
Washer
Dryer

House Rules

Check in after 4:00 PM

Minimum age to rent: 25

Check out before 10:00 AM

Children

Children allowed: ages 0–17

Events

No events allowed

Pets

No pets allowed

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 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 fire extinguisher, a first aid kit and a deadlock

We should mention

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. 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. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Islamorada, FL

What's nearby

Islamorada Brewery & Distillery - 6 min walk - 0.6 km
Florida Keys Brewing Co. - 2 min drive - 2.3 km
Windley Key Fossil Reef Geological State Park - 4 min drive - 4.0 km
Theater of the Sea - 4 min drive - 4.3 km
Bud n' Mary's Dive Center - 6 min drive - 5.7 km

Getting around

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

Restaurants

‪Lorelei Restaurant & Cabana Bar - ‬15 min walk
‪Florida Keys Brewing Co. - ‬2 min drive
‪Wendy's - ‬11 min walk
‪The Trading Post - ‬18 min walk
‪Islamorada Beer Company - ‬9 min walk

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).

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.

Learn more

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

10/10 Excellent

william c.

19 Aug, 2025

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

George C.

10 Jun, 2025

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

Property was very nice and well appointed.

Stayed 7 nights in May 2025

10/10 Excellent

donald n.

10 Aug, 2025

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.

15 Jul, 2025

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.

17 Mar, 2025

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.

18 Feb, 2025

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

Phil T.

2 Nov, 2024

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

Andrew C., USA

19 Nov, 2023

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

Edward M.

26 Aug, 2024

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

Shannon S.

12 Dec, 2024

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

Aaron G.

25 Jul, 2020

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

10/10 Excellent

Judy M.

19 Aug, 2019

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

10/10 Excellent

Judy M.

15 Oct, 2018

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

10/10 Excellent

Luke B.

18 Feb, 2023

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

Paradise

Clean quiet and tranquil.

Stayed 7 nights in Feb 2023

10/10 Excellent

Laurie B.

10 Jan, 2022

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

10/10 Excellent

Janna S.

31 Dec, 2018

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

Judy M.

17 Apr, 2019

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

10/10 Excellent

Matt U.

5 Jul, 2018

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

2 Jan, 2022

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

Lori H.

21 Feb, 2024

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

Jeff S.

28 Jan, 2024

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

Brian B.

25 Jan, 2021

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

10/10 Excellent

Sharman U.

6 Oct, 2020

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.

8 Dec, 2021

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

love

The ocean is awesome!!!

Stayed 7 nights in Nov 2021

10/10 Excellent

Linda C.

27 Mar, 2023

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