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Compare 456 Villas in Osprey with updated reviews, rates, and availability.

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

9.8 out of 10, Exceptional, (105)
"We had the greatest little getaway here! The place was clean and stocked with everything we needed, including beach supplies. It was awesome to walk directly onto the beach :) We can’t wait to come back! "
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!

Waterfront Villa Seaglass

9.8 out of 10, Exceptional, (80)
"The property was situated perfectly between the bay and the ocean. The heated pool was great for this time of year. It was the right size for a family of four and had great restaurants within walking distance or a short drive. Would stay again!"
Waterfront Villa Seaglass

Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

9.8 out of 10, Exceptional, (94)
"This was my 4th year staying Barefoot Bungalows.The location is the best for the price After the hurricanes last year, the unit was clean and ready to enjoy. The manager, Lisa, even supplied a certification of being mold free. This is my 4th year and will be back next year. Everything you need to make your stay convenient is already there. Beach towels, beach chairs, beach umbrella, and even a cooler for drinks and snacks plus wagon to take everything to the beach. Thank you again Lisa for the...
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (59)
"Enjoyed our stay.. Very nice property .. enjoyed the pool and sunrises!!... Short walk to beach and use of chairs ,etc for beach.. Thanks!!"
Waterfront Mermaid's Retreat Delights!

Lanai + Community Pool Access: Sarasota Oasis!

9.2 out of 10, Wonderful, (14)
"This property was exactly as represented and was just like home for comfort and functionality!! Well stocked kitchen for cooking. Beautiful private lanai with occasional sightings of bunnies in the backyard.Easily accessed Tamiami highway which connects to all things Florida!! We used the pool several days. Very clean area with plenty of loungers. Will definitely book this property again!"
Lanai + Community Pool Access: Sarasota Oasis!

Paradise Cove at Lemon Bay

3.5 star property
8.0 out of 10, Very Good, (75)
"The property was outstanding. The owners were marvelous would definitely go back."
Paradise Cove at Lemon Bay

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (114)
"Would love to come back"
Venice Island / Venice Beach Luxury Villa

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
10.0 out of 10, Exceptional, (1)
"Buenas condiciones. "
6 BR Heated Pool, Mins from IMG and Anna Maria

Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!

10.0 out of 10, Exceptional, (13)
"This was a great find close to the beach. The villa had a lot of great appliances for those with shorter or extended stays. Can’t wait to stay here again! Highly recommend!! "
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!

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

10.0 out of 10, Exceptional, (37)
"Wonderful hosts and we had a fantastic stay. Walking distance to the beach, plenty to see and do in the area. We can't wait to return and stay at the Flamingos Nest. "
The price is AED 748
AED 1,793 total
includes taxes & fees
28 Apr - 29 Apr
Flamingo's Nest at the Beach Shack. Just one block from the beach!

Completely Remodeled- 150 Yards to Beach and Restaurants!

10.0 out of 10, Exceptional, (31)
"Property was really nice. The owners were easy to work with and communicated really well. Easy walk to the beach and conveniently located across the street from restaurants with good food. "
The price is AED 1,010
AED 1,963 total
includes taxes & fees
21 Apr - 22 Apr
Completely Remodeled- 150 Yards to Beach and Restaurants!

Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool

10.0 out of 10, Exceptional, (2)
"This booking was 5/5 stars in every way! Booking was easy, communication was prompt and thorough, and the home is amazing. Very clean and freshly updated, plentiful necessities, beautiful pool (with a dedicated poolside bathroom and shower) and a master bath with a shower to die for! We loved our week and hated to leave!! Would not hesitate to rent again."
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool

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

9.4 out of 10, Exceptional, (50)
"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 AED 404
AED 1,115 total
includes taxes & fees
29 Apr - 30 Apr
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk

Casa Blanca Villa C05

9.8 out of 10, Exceptional, (9)
"Great location, friendly, and hospitality. Staff was very helpful and friendly, Jeff bailed us out with a difficulty in the laundry room."
Casa Blanca Villa C05

Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

10.0 out of 10, Exceptional, (6)
"This place exceeded our expectations! Everything was clean and the furniture was comfortable. The kitchen is perfect with the appliances and the washer dryer a huge plus! The location to the beach and other fun things to do! Communication was great, check in and check out was super easy! Hopefully we will be back again!!"
Renovated 1 Bed / 1 Bath Condo on Siesta Beach!

Casa Blanca Villa D08

9.4 out of 10, Exceptional, (16)
"Everything were perfect"
Casa Blanca Villa D08

Siesta Key Palm Paradise with Heated Saltwater Pool

9.8 out of 10, Exceptional, (12)
"Pool was nice"
Siesta Key Palm Paradise with Heated Saltwater Pool

Waterfront Paradise Bay

10.0 out of 10, Exceptional, (76)
"Really comfortable stay. Beautiful location. The pool was great and it’s such a short walk to the beach. Our family had a great time! "
Waterfront Paradise Bay

Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly

10.0 out of 10, Exceptional, (137)
"Our 2 sons and their families loved, loved, loved this property. The room set ups, 2 bathrooms we nice, nice kitchen, and laundry. So close to the beach with lots of sharks teeth but no sharks great response from host when we had questions. "
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly

2 Minute Walk to Siesta Beach -really!! Great value, great location !!!

9.8 out of 10, Exceptional, (56)
"Wonderful hosts. Fantastic communication."
2 Minute Walk to Siesta Beach -really!! Great value, great location !!!
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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Other property types in Osprey

Huge Pool, Close to Beaches, Restaurants, Shopping & More!

9.6 out of 10, Exceptional, (22)
"What a wonderful place to relax! Will definitely recommend to family and friends and even come back to stay!"
Huge Pool, Close to Beaches, Restaurants, Shopping & More!

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4627)
"Nice place and clean! Staff was very friendly and helpful. "
The price is AED 590
AED 750 total
includes taxes & fees
20 Apr - 21 Apr
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2113)
"Location is great..Crescent Beach within a reasonable walking distance. The suite was clean and comfortable. The staff were very helpful. The pool is a nice feature. Extra amenities like beach towels, chairs , umbrellas, grills to cook on were nice. Only negative was that the street is busy so the traffic is a little loud by the pool or if you are sitting outside your room. Inside it is not a bother.This is my second time here... I would come back."
The price is AED 606
AED 684 total
includes taxes & fees
1 May - 2 May
Hibiscus Suites - Gateway to Siesta Key
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.

Frequently asked questions

How much do villas in Osprey cost?
Villas in Osprey cost between AED 748 and AED 748 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?
A guest favorite is Island House Beach Resort V39. Settle in at this 3-star property which offers a barbecue grill and a swimming pool. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another popular option worth considering. Book into this 2.5-star stay and you’ll have access to conveniences like a barbecue grill and a swimming pool. You can pick from multiple villas in Osprey with a total average guest review rating of 9.8.
How many villas are there in Osprey?
Take your pick of 456 villas in Osprey. No matter if you’re vacationing with the family or getting away with some friends, Expedia will help you find the best space for your whole crew.