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Check prices for these dates

Next weekend
18 Rab. II - 20 Rab. II
In two weeks
25 Rab. II - 27 Rab. II
In one month
9 Jum. I - 11 Jum. I
In two months
6 Jum. II - 8 Jum. II

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

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

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
A heated pool

Waterfront Villa Seaglass

9.8 out of 10, Exceptional, (80)
"We loved our stay here. It is a secluded spot right on the bay. So you can enjoy the pool, beach, fish and the small town that’s 1.5 miles up the road. Owner was great and process was smooth too. "
Waterfront Villa Seaglass
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Terrace/patio

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

9.8 out of 10, Exceptional, (93)
"Totally as advertised. Short distance from a wonderful beach and all of the stuff you would need - wagon, chairs, towels etc. The cottage is very nice. Comfy bed and plenty of towels with a hot shower. We loved being walking distance to the old village shopping area for groceries and restaurants and entertainment. We hardly moved our car the whole week. Would rent again. "
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3
Waterfront Mermaid's Retreat Delights!
A heated pool

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (58)
"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!
Pool

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
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, (114)
"Would love to come back"
Venice Island / Venice Beach Luxury Villa
6 BR Heated Pool, Mins from IMG and Anna Maria
Property grounds

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
6 BR Heated Pool, Mins from IMG and Anna Maria
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Terrace/patio

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

10.0 out of 10, Exceptional, (12)
"We stayed in this rental for the month of Jan 2025. It was very comfortable and well equipped. We particularly enjoyed the large grill in the patio for cooking. The best feature was the convenient location - 12 minutes to Siesta Key Beach or downtown Sarasota, 15 minutes to St. Armands and Lido Beach, walking distance to grocery and drug stores, a few restaurants, and Barnes and Nobles. Our host Mark was very responsive and available for anything we needed throughout our visit. A very...
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Flamingo's Nest at the Beach Shack. Just one block from the beach!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (36)
"Beautiful, quaint cottage with everything you need to make a great beach experience! Heather thought of everything!! "
The price is SAR 764
SAR 1,852 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!
Outdoor pool, a heated pool

Completely Remodeled- 150 Yards to Beach and Restaurants!

10.0 out of 10, Exceptional, (31)
"Beautiful condo with perfect location to both the beach and restaurants and trolley. Will definitely stay here again!! 7-11 right across the street, and Captain Curt’s so close!!!!!"
The price is SAR 1,033
SAR 2,030 total
includes taxes & fees
15 Apr - 16 Apr
Completely Remodeled- 150 Yards to Beach and Restaurants!
Huge Beach Villa, Mins To Beach With Private Salt Water Heated Pool
Outdoor pool, a heated pool

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
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 SAR 545
SAR 1,299 total
includes taxes & fees
29 Apr - 30 Apr
Drift Inn B, Heated Pool, Beach and Amenities, 2-3 min walk
Casa Blanca Villa C05
Pool

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
Private kitchen

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, (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
TV

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

10.0 out of 10, Exceptional, (136)
"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 !!!
Fridge, microwave, oven, stovetop

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
Family Suite, 2 Bedrooms (Preferred Suite) | Premium bedding, pillowtop beds, in-room safe, iron/ironing board

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4619)
"Loved Yropical Beach Resort. Would definitely stay here again!"
The price is SAR 603
SAR 767 total
includes taxes & fees
21 Apr - 22 Apr
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, (2111)
"Everything was good "
The price is SAR 619
SAR 699 total
includes taxes & fees
8 May - 9 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 and 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 .
How many villas are there in Osprey?
Take your pick of 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.
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.