Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock, 5BR/3BA, Sleeps 10, Islamorada

See all properties

Entire home

Overview
Amenities
Policies
Location
Host

Exceptional

5 bedrooms3 bathroomsSleeps 10488.2 sq m

Popular amenities

Parking available
Dryer
Air conditioning
Washer

Explore the area

Islamorada, FL

Islamorada Brewery & Distillery
‪9 min walk‬
Florida Keys Brewing Co.
‪2 min drive‬
Theater of the Sea
‪3 min drive‬
Marathon, FL (MTH-Florida Keys Marathon)
‪40 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 Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

OSPREY BAY VILLA! Wonderful Bay front Home in the heart of Islamorada in the fabulous Florida Keys for rent by the week, or month; offering Incredible Panoramic Bay and Sunset Views. Heated pool & hot tub, sunning decks galore. Deep water dock & boat basin. Elegant, yet casual, spacious living room with coral rock fireplace, wet bar, open dining room, atrium garden,& gourmet kitchen. Sleeps 10-12 people comfortably. Private south wing offers 3 bedrooms; 1 with1 king bed, 1 with 1 queen bed, another 1 with 2 queen beds, and 1 full bathroom with bathtub & separate shower, double vanity sinks etc. Separate bedroom with two twin beds, tv, a/c, etc. adjacent to kitchen. Spacious second level master bedroom suite with king bed & it's own master bath & vanity room, fireplace & bay side veranda. Third full bathroom with vanity and shower downstairs has an entrance from the wet bar/living room area & also exits to and from the heated pool. Lush tropical landscape & expansive waterfront lawn & dock area with its own small beach for wading into bay, for snorkeling or for an easy launch for kayaks and paddleboards. This vacation home is secluded, yet situated in a perfect location for walking to classic restaurants & local shops.
Come, Relax & Enjoy!

Keywords: House

Property manager

Judy Moeller

Languages

English

Add dates for prices

Amenities

Pool

Hot tub

Kitchen

Washer

Dryer

Free WiFi

Have a question?

Beta

Get instant answers with AI powered search of property information and reviews.

Ask a question

Similar properties

Ocean view
Pool
Kitchen
Washer

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.

View more Holiday homes in Islamorada

Islamorada, FL

What's nearby

History of Diving Museum - 9 min walk - 0.8 km
Islamorada Brewery & Distillery - 9 min walk - 0.8 km
Florida Keys Brewing Co. - 2 min drive - 2.2 km
Theater of the Sea - 3 min drive - 3.4 km
Bud n' Mary's Dive Center - 4 min drive - 4.6 km

Getting around

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

Restaurants

‪Lorelei Restaurant & Cabana Bar - ‬17 min walk
‪Islamorada Fish Company - ‬3 min drive
‪Wahoo's Bar & Grill - ‬2 min drive
‪Green Turtle Inn - ‬3 min drive
‪Florida Keys Brewing Co. - ‬2 min drive

Frequently asked questions

Does Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!! have a pool?

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

Is Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!! pet-friendly?

No, pets are not allowed at this property.

What time is check-in at Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!?

Check-in begins at 4:00 PM.

What time is check-out at Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!?

Checkout is at 10:00 AM.

Where is Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & 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

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

Mary O.

21 Dec 2024

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.

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

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

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

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

colleen c.

14 Feb 2024

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.

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

Laura K., NC, USA

9 Jan 2024

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

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

Susu D.

22 July 2023

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

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

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

ken M.

11 Jan 2023

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.

27 Nov 2022

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

10/10 Excellent

Carey N.

12 July 2022

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

Wonderful!!

This was a fantastic place! It had everything we needed inside and out. We spent most of our time on the dock fishing and enjoying the water. Besides the amazing fish, including nurse sharks and lemon sharks, we saw manatees almost everyday. The pool and eco area were great and had tons of pool rafts/toys. The house was one of the most fully equipped houses we’ve stayed in. Everything was labeled and easy to find and in great condition. Would love to stay here again!!

Stayed 7 nights in Jul 2022

10/10 Excellent

Rob C.

12 June 2022

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

Family Vacation

This property is exceptional and exceeded all of our expectations! The entire week was filled with memorable experiences that we enjoy as a family: boating, kayaking, fishing, snorkeling, wildlife and overall experiences the outdoors offers. Also there are great restaurants and bars in close proximity by boat and car.

Stayed 7 nights in Jun 2022

10/10 Excellent

Phil T., Ross-on-Wye

23 Apr 2022

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

Excellent getaway for the whole family

Does what it says on the tin. Great location and Judy and Ken made us all feel very welcome. Hopefully we will all return in the near future.

Stayed 14 nights in Apr 2022

10/10 Excellent

rita j.

11 Apr 2022

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

April 2022

The BEST we have stayed in in the keys. We have been going to the Keys for 30 years. This was the best experience from booking to the end. Judy was very accommodating and thoughtful!!! We are hoping to make this an annual trip to this property!!!

Stayed 7 nights in Apr 2022

10/10 Excellent

Ellen B., Saint Louis, mo

16 Feb 2022

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

Hopefully stay here again

Loved the location. The back yard is like an oasis with the privacy, the pool, hot tub and the dock. Saw lots of fish, dolphins and even a shark one evening. House has plenty of space for a group, so you don't feel like you're on top of each other. We all spent most of the time outside and the spacious dock, deck and pool areas. House is dated, but very well maintained and cleaned.

Stayed 7 nights in Jan 2022

10/10 Excellent

Carol S.

22 Jan 2022

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

Family vacation

Great time children and grandchildren

Stayed 7 nights in Jan 2022

10/10 Excellent

Sherri B.

18 Jan 2022

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

Private oasis

What an amazing way to ring in 2022 and spend my 50th birthday with friends and family. The house is spacious and well-equipped, but the pictures don't do justice to the outside space. The weather wasn't fabulous, but that's ok when you have a heated pool and hot tub overlooking the water and snorkeling off your own dock! We ranged from age 10 to age 80, and every single person enjoyed the relaxed environment created by Osprey Bay Villa. Thank you, Judy, for sharing your home with us! We are already looking to come back next year! :)

Stayed 7 nights in Jan 2022

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

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

Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Photo gallery for Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Reviews

Popular amenities

Explore the area

Rooms & beds

5 bedrooms (sleeps 10)

Bedroom 1

Bedroom 2

Bedroom 3

Bedroom 4

Bedroom 5

3 bathrooms

Bathroom 1

Bathroom 2

Bathroom 3

Spaces

About this property

Osprey Bay Villa on Fla. Bay-Has it all! Spectacular Sunsets, pool, spa & dock!!

Property manager

Languages

Add dates for prices

Amenities

Have a question?

Similar properties

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

Oceanfront Estate with Private 350 foot Pier, Heated Pool, Pet Friendly

House Rules

Children

Events

Pets

Smoking

Important information

You need to know

We should mention

About the area

Islamorada

What's nearby

Getting around

Restaurants

Frequently asked questions

Reviews

Exceptional

10/10

10/10

10/10

10/10

10/10

Reviews

10/10 Excellent

kathryn u.

Great house

kathryn u.

10/10 Excellent

Jeff S.

Great week

Jeff S.

10/10 Excellent

Mary O.

Fantastic week- love

Mary O.

10/10 Excellent

Shannon S.

Islamorada Thanksgiving

Shannon S.

10/10 Excellent

Phil T.

Return Guests - As good as last time

Phil T.

10/10 Excellent

Edward M.

Review

Edward M.

10/10 Excellent

Lori H.

Howell

Lori H.

10/10 Excellent

colleen c.

Family getaway