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Check prices for these dates

In two weeks
24 Oct - 26 Oct
In one month
7 Nov - 9 Nov
In two months
5 Dec - 7 Dec
In three months
2 Jan - 4 Jan

Featured Villas in Osprey and around

❤️️Luxury Villa in Englewood, Private Pool 😎, Game Room, 6 mins to Beaches
Pool

❤️️Luxury Villa in Englewood, Private Pool 😎, Game Room, 6 mins to Beaches

10.0 out of 10, Exceptional, (2)
"The house is spotlessly clean and beautifully decorated. Extremely comfortable with every possible amenity. Quiet neighborhood close to the beaches. The hosts were easily accessible. Top rating!! We will definitely return."
The price is €333
includes taxes & fees
15 Oct - 16 Oct
❤️️Luxury Villa in Englewood, Private Pool 😎, Game Room, 6 mins to Beaches
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Exterior

Flamingo's Nest at the Beach Shack. Just one block from the beach!

10.0 out of 10, Exceptional, (39)
"Location was great, property condition is excellent!"
The price is €290
includes taxes & fees
13 Oct - 14 Oct
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Seashell Shanty at The Beach Shack! Come On Down!
Terrace/patio

Seashell Shanty at The Beach Shack! Come On Down!

10.0 out of 10, Exceptional, (42)
"This property is amazing . We had a great time.....all the extras are such an added benefit!"
The price is €290
includes taxes & fees
19 Oct - 20 Oct
Seashell Shanty at The Beach Shack! Come On Down!
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Exterior detail

Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool

9.8 out of 10, Exceptional, (7)
"Very relaxing..very spacious..decor was outstanding..very clean .and inviting..love it"
The price is €690
includes taxes & fees
9 Oct - 10 Oct
Stunning Retreat: Endless Summer Villa 3BR/ 2BA with Heated Pool
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Exterior

Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

9.4 out of 10, Exceptional, (51)
"Stayed at the property prior to our cruise out of port canaveral. Was perfect for our needs - steps to the beach and close to many stores/cafes/etc. would definitely stay again. "
The price is €263
includes taxes & fees
12 Oct - 13 Oct
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
Outdoor dining

2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A

10.0 out of 10, Exceptional, (1)
"Perfect getaway"
The price is €324
includes taxes & fees
9 Oct - 10 Oct
2 Bedroom/2 Bath Villa (Ground Level) - Unit 4/A
Pineapple Express at the Beach Shack Just one block from the beach!
Exterior

Pineapple Express at the Beach Shack Just one block from the beach!

10.0 out of 10, Exceptional, (37)
"Great stay"
The price is €418
includes taxes & fees
12 Oct - 13 Oct
Pineapple Express at the Beach Shack Just one block from the beach!
Seaglass Inn at the Beach Shack Just one block from the beach!
Exterior

Seaglass Inn at the Beach Shack Just one block from the beach!

10.0 out of 10, Exceptional, (23)
"It was very clean, very nice place with tons to offer."
The price is €418
includes taxes & fees
9 Oct - 10 Oct
Seaglass Inn at the Beach Shack Just one block from the beach!
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
Property grounds

Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool

9.0 out of 10, Wonderful, (4)
"We had the best time. Our host Melissa was amazing. "
The price is €611
includes taxes & fees
8 Nov - 9 Nov
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
The Oceanview Oasis
Interior

The Oceanview Oasis

10.0 out of 10, Exceptional, (125)
"We loved our little island stay, the beach was as beautiful as the pictures! Clean and a such a short distance to everything, we will definitely be staying again! "
The price is €291
includes taxes & fees
13 Oct - 14 Oct
The Oceanview Oasis
Pet Friendly Tropical Villa, Heated Salt Pool
Exterior

Pet Friendly Tropical Villa, Heated Salt Pool

10.0 out of 10, Exceptional, (3)
"We had a great vacation! We were happy with the cleanliness and the communication for our stay!"
The price is €571
includes taxes & fees
9 Oct - 10 Oct
Pet Friendly Tropical Villa, Heated Salt Pool
Completely Remodeled- 150 Yards to Beach and Restaurants!
Exterior

Completely Remodeled- 150 Yards to Beach and Restaurants!

10.0 out of 10, Exceptional, (36)
"Cute, Clean and Convenient!"
The price is €364
includes taxes & fees
23 Oct - 24 Oct
Completely Remodeled- 150 Yards to Beach and Restaurants!
Side-by-Side Villas for Groups Near Downtown
Miscellaneous

Side-by-Side Villas for Groups Near Downtown

The price is €2,730
includes taxes & fees
27 Oct - 28 Oct
Side-by-Side Villas for Groups Near Downtown
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
Property grounds

2 Bedroom/2 Bath Villa (Ground Level) - Unit 7

10.0 out of 10, Exceptional, (2)
"Clean and updated cottage across the street from beach and walking distance to two restaurants. Responsive management and easy to work with. Quiet sleeping . Nice stay"
The price is €324
includes taxes & fees
9 Oct - 10 Oct
2 Bedroom/2 Bath Villa (Ground Level) - Unit 7
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
Outdoor dining

ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8

10.0 out of 10, Exceptional, (4)
"Had a very relaxing time. Nice short walk to the beach"
The price is €212
includes taxes & fees
13 Oct - 14 Oct
ADA Compliance - 1 Bedroom/1 Bath Villa (Ground Level) - Unit 8
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
Fridge, microwave, oven, stovetop

2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C

The price is €324
includes taxes & fees
19 Oct - 20 Oct
2 Bedroom/2 Bath Villa (Ground Level) - Unit 9/C
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
Property grounds

3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B

10.0 out of 10, Exceptional, (1)
"The escape at Casey key was a great place to stay , was clean rooms were nice and updated and look forward to next Memorial Day weekend"
The price is €509
includes taxes & fees
28 Oct - 29 Oct
3 Bedroom/2 Bath Villa (Ground Level) - Unit 5/B
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Osprey Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"It was a really pleasant stay. I recommend the property, breakfast was excellent and the front desk staff were professional, welcoming and friendly. "
Jose 1-night trip
Posted 2 days ago
Carlisle Inn

Find out more about Osprey

Find out more about Osprey

Osprey Villas information

Number of reviews
354
Accommodation
426 Villas
Lowest Price
€212
Highest Price
€2,730

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between €212 and €2,730 per night. These getaways provide the privacy to enjoy your own space at a price that won't stretch the budget. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best villas in Osprey?
Osprey has multiple villas with a total average guest review rating of 9.8. Island House Beach Resort V39 is a popular choice with Expedia guests. Visitors staying at this 3-star retreat will enjoy access to a swimming pool and a barbecue grill. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another sought-after stay. This 2.5-star villa offers a barbecue grill and a swimming pool, among other conveniences.
How many villas are there in Osprey?
Take your pick of 426 villas in Osprey. No matter if you're holidaying with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.
What are the best cheap villas in Osprey?
Villas start at €212 per night, so your Osprey adventure doesn't have to stretch your budget! Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is a pocket-friendly pick that comes with plenty of amenities, including a barbecue grill and a swimming pool. Island House Beach Resort V21 is another cheap stay in this sought-after destination. Amenities here include a barbecue grill and a swimming pool. If you're exploring Osprey on a budget, there are loads of popular and free attractions to add to your to-do list. Siesta Key Beach and Venice Beach are visitor favourites. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly villas in Osprey?
Many visitors needing a family-friendly villa in Osprey go for Island House Beach Resort V39. With a 3-star rating and useful amenities like a barbecue grill and clothes washing facilities, you're sure to feel at home here. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is a 2.5-star stay that's also a hit with travelling families. Clothes washing facilities and WiFi help make it a comfy base for your Osprey getaway. Once you've checked in and unpacked your suitcase, there's no shortage of family-friendly attractions to see around Osprey. Siesta Key Beach and Venice Beach guarantee a good time for young and old.
Why book your villa in Osprey with Expedia?
Expedia makes it a cinch to find your dream villa in Osprey. Getting away with the family? Make the most of our filters to search for stays with amenities like WiFi and a pool. If you need to stick to a budget, choose how much you're willing to spend and the star rating of the property. We'll help you find a perfect place that matches your style and taste.
How can I find cheap villas in Osprey?
The quickest way to zero in on cheap villas in Osprey is with Expedia's handy filter tool. Tailor your search results by amenities, budget and star rating to nab unbeatable prices in just a couple of clicks.
What is there to do near my villa in Osprey?
After you've unpacked your suitcases, set out and explore the fun things Osprey has for you to experience. Oscar Scherer State Park is a popular attraction to add to your to-do list.