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Check prices for these dates

Next weekend
9 May - 11 May
In two weeks
16 May - 18 May
In one month
30 May - 1 Jun
In two months
27 Jun - 29 Jun

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

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

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

9.8 out of 10, Exceptional, (107)
"Best sunset ever. The area is recovering from late 2024 hurricanes. Unit and host were perfect for what we wanted."
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Waterfront Villa Seaglass
A heated pool

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
Beach nearby, sun loungers, beach towels

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!
Aerial view

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (60)
"This rental was nice. It had close proximity to the beach and beautiful views of the bay. We saw manatees swimming one evening! "
Waterfront Mermaid's Retreat Delights!
Lanai + Community Pool Access: Sarasota Oasis!
Pool

Lanai + Community Pool Access: Sarasota Oasis!

9.6 out of 10, Exceptional, (13)
"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
Exterior

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
Beach

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (115)
"My husband and I love Venice. We love the slower pace of life, the lazy beach days and walks downtown. What we loved most about this villa was the location. It is a short walk to the beach and a short walk downtown - we enjoy being outside and getting our steps in, so for us this was perfect. Some reviews said they thought the beach would be closer, which we did too - but that was more because the Google View shows a different villa, not VRBOs fault. The villa was stocked with all essentials and...
Venice Island / Venice Beach Luxury Villa
6 BR Heated Pool, Mins from IMG and Anna Maria
Terrace/patio

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!
Beach nearby, sun loungers, beach towels

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!
Beach nearby

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 720
AED 1,780 total
includes taxes & fees
29 May - 30 May
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Completely Remodeled- 150 Yards to Beach and Restaurants!
Exterior

Completely Remodeled- 150 Yards to Beach and Restaurants!

10.0 out of 10, Exceptional, (32)
"I wish I could give this place 10 stars. It’s beautifully remodeled and has everything a small group could ask for. When we arrived, it was spotless and well-stocked with pots, pans, TP, paper towels, you name it. The beds were super comfortable and we both slept like the dead, even though this place is located on a busy road. The road noise didn’t bother us one bit. The duplex is conveniently located on Midnight Pass road and across the street from a free trolley stop, so getting into the...
The price is AED 735
AED 1,637 total
includes taxes & fees
13 May - 14 May
Completely Remodeled- 150 Yards to Beach and Restaurants!
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool
Interior

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
Fridge, microwave, oven, stovetop

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 1,129 total
includes taxes & fees
7 May - 8 May
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Casa Blanca Villa C05
Beach nearby

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!
Pool

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
Beach nearby

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
A heated pool

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
A heated pool

Waterfront Paradise Bay

10.0 out of 10, Exceptional, (77)
"We live in Florida and wanted a mini vacation away from home. This was the perfect place. We stayed in Paradise Bay. Short walk to a beautiful beach. Doc right out back for fishing. Place is very well kept. We will be hopefully vacationing here again soon. "
Waterfront Paradise Bay
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
Sun loungers, beach towels

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

10.0 out of 10, Exceptional, (138)
"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 !!!
Beach nearby, sun loungers, beach umbrellas, beach towels

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!
Smart TV, foosball, books

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
Property amenity

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4642)
"The hotel is next to the beach, walking to the beach is easy. A lot of dinning options just several minutes walking away. Even due to cutting the tree we couldn’t park the car next to our room, but the staff offered parking very close by. Front desk was very nice and helpful as well. "
The price is AED 538
AED 691 total
includes taxes & fees
27 May - 28 May
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2120)
"Excellent customer service, clean and easy access to dining and the beach "
The price is AED 587
AED 664 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 404 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 9.7.
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.