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Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! | House in Islamorada

10.0 (92 Reviews) |   5 Bedrooms  3 Bathrooms  10 Guests
Islamorada House | Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock!

5 Bedroom House in Islamorada

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.

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! is located in Islamorada. Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! provides accommodation, featuring Air Conditioner, Private Pool, Security/Safety, among other amenities. This House features Air Conditioner, Parking and Pool to make your stay a comfortable one.

Osprey Bay Villa on the Bay! Spectacular Sunsets, Pool, Hot Tub & Private Dock! has 5 Bedrooms , 3 Bathrooms, and max occupancy of 10 people. The minimum rental for this property is 1 nights, but this can change depending on the season you plan on staying. Previous guests have given good rated it, and VRBO labeled it a top-rated House because of the excellent services rendered by the owner or manager of this House, and has consistently provided great experiences for their guests. Most families or guests that use it recommend it to their friends and some of them are repeat guests. House has a friendly neighborhood, and the Islamorada has interesting places to visit. If you want to learn more about the House in Islamorada, such as places to visit and things to do nearby, you can check below to learn more.

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Amenities

Air Conditioner
Parking
Pool
TV
View
Private Pool
Balcony/Terrace
Security/Safety
Sports/Activities
Bedding/Linens
Wellness Facilities
Fireplace
Guest Services
Entertainment
Barbecue/Outdoor Cooking
Child Friendly
Heating
Hot Tub
Internet
Kitchen
Laundry

Facility Overview

Air Conditioner
  • Heating
  • Air conditioning
Bathrooms
  • Soap
  • Shampoo
  • Towels provided
  • Toilet paper
  • 3 bathrooms
  • Hair dryer
Bedroom
  • Dining table
  • 5 bedrooms
  • Bed sheets provided
  • Fireplace
Kitchen
  • Blender
  • Oven
  • Stovetop
  • Electric kettle
  • Ice maker
  • Dishwasher
  • Refrigerator
  • Spices
  • Microwave
Laundry
  • Washing machine and dryer
  • Near laundromat
  • Laundry facilities
Ocean view
  • Beach towels
  • Beach sun loungers
Parking
  • Onsite parking
  • Car required
Pet Friendly
  • No pets allowed
Accessibility
  • Smoke-free property
  • Upper floors accessible by stairs only
  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • Wheelchair-accessible path of travel
  • No elevators
Activities
  • Marina nearby
  • Fishing nearby
  • Basketball nearby
  • Power boating nearby
  • Windsurfing nearby
  • Tennis on site
  • Water park nearby
  • Fitness facilities nearby
  • Golf nearby
  • Birdwatching nearby
  • Ecotours nearby
Entertainment
  • Smart TV with cable/satellite service
  • Books
  • Video library
  • Stereo
  • DVD player
  • Music library
General
  • Printer
  • English
  • Near a health or beauty spa
  • Near a hospital
  • On the waterfront
  • Near a zoo
  • Unit size: 5255 sq ft (488 sq m)
Guest Services
  • Children's dinnerware
  • Highchair
  • Playground
  • Travel crib
  • Children's books
  • Iron/ironing board
  • Phone
Internet
  • Free WiFi
Outdoors
  • Balcony
  • Outdoor furniture
  • Garden
  • Barbecue grill
Security/Safety
  • Smoke detector installed (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher
  • Carbon monoxide detector installed (host has indicated there is a carbon monoxide detector on the property)
  • Deadbolt lock
Spa
  • Fence around the pool
  • Private pool
  • Hot tub
  • Heated pool

Policies

Check-in
Check-in time starts at 4:00 pm contactless check-in available minimum check-in age: 25
Check-out
Check-out before 10:00 am
Child Policy
Children are welcome.
Event Policy
No events allowed
Pet Policy
Pets not allowed
Smoking Policy
Smoking is not permitted

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 this property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room this property is managed through our partner, vrbo. you will receive an email from vrbo with a link to a vrbo account, where you can change or cancel your reservation

Reviews

William S.
Jul 5, 2026 09:06:45 AM
Review Score:   10
Summary: We had a wonderful week at Osprey Bay! Judy was a great host and had much to offer in terms of boating/restaurant recommendations. Centrally located in Islamorada, all of the restaurant favorites are 10 minutes drive. The house is located down a long driveway, offering a great deal of privacy. Inside, everything you need is available and extremely clean. We enjoyed the beautiful pool and swimming from the dock. There is a school of parrotfish that live in and around the dock, along with occasional manatee sightings. The protected basin offers easy navigation while boating with multiple access points to the Atlantic. In every direction the water is always 4-10 feet deep with lots of seagrass and top to bottom visibility. We were able to reach Alligator Reef within 30 minutes from the backyard dock. Finally, you have a world class seat for each magnificent sunset.
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FAQ's

Is this property pet-friendly for guests?

No, pets are not allowed at this property. Check the guest reviews to learn what guests had to share.

Does the property have a swimming pool?

Yes, this Islamorada house has a swimming pool. Check the Facility Overview section for details about the pool and other available facilities.

How much does it cost per night to stay in property?

Best-rates for the Islamorada house starts from $1,444 per night with includes Parking, View, Fireplace, Heating, Laundry, Air Conditioner, Private Pool, Security/Safety, Sports/Activities, Bedding/Linens, Guest Services, Barbecue/Outdoor Cooking, Hot Tub, Internet, Wellness Facilities, Entertainment, Pool, TV, Balcony/Terrace, Child Friendly, Kitchen with all other facilities. matches every traveler with their perfect accommodation, whether you are traveling with a group, friends, family, or pets.

Is property a family-friendly place to stay?

Based on the information we have received from the owner or our partner, this is considered to be a family-friendly property. Families have rated this house Good or guests have recommended them suitable for families. As reported by the owner or manager, the house has specified that children are welcome. Please see details about suitability for your family or inquire with the property to learn more.

Is the property wheelchair accessible or offer services for disabled guests?

Based on the information received from our partner, the Islamorada house has not specified they are wheelchair accessible. Likewise, there is not an elevator specified as being available at the property. Specific accessibility details may be addressed in the property details section of this page.

What is the minimum night stay policy for the property?

Based on the information reported by the owner or manager, the Islamorada house indicates 1 day stay policy at this house. Guests are cautioned that the minimum stay policy may differ based on seasonality or availability and may be at the discretion of the owner or manager.

What cancellation policy is in place for property?

Guests are cautioned that the cancellation policy may differ based on seasonality, availability, or current travel restrictions. Guests should also be aware that this policy may be subject to change and should be confirmed prior to booking. More details may be available on this page in the property description. However, early check-in or late check-out can sometimes be negotiated between the guest and the owner or the manager of this property.