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Compare 385 Villas in Osprey with updated reviews, rates, and availability.

Waterfront Mermaid's Retreat Delights!

9.8 out of 10, Exceptional, (52)
"All was great. Only want to point out that the door leading into bathroom was stuck and appears to be water damaged or rotted in the bottom. Also could not turn on the main light by living room/kitchen area. Not complaining, just thought you should know. "
Waterfront Mermaid's Retreat Delights!

Waterfront Villa Seaglass

10.0 out of 10, Exceptional, (73)
"Villa is very nice. Great location with beautiful view of Lemon Bay. Very quiet and relaxing. We will be back. "
Waterfront Villa Seaglass

Beachy 3-bedroom Villa on Siesta Key with WiFi, AC

10.0 out of 10, Exceptional, (2)
"Fully remodeled 3bedroom house walking distance (5-8min) to the beautiful beach. The house is spic-n-span clean, new appliances, dishes, towels, beach cooler, beach chairs, beach canopy. There is a beach cart available, which is very convenient. Beautiful warm pool within 1-2 min walk from the house. "
Beachy 3-bedroom Villa on Siesta Key with WiFi, AC

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!

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

9.8 out of 10, Exceptional, (90)
"Great place! Perfect location. Could not have been better!"
Siesta Key 2BR 1Bath unit COZY at 1945 Barefoot Bungalows 1500 ft from access#3

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (113)
"The property was in a great location to the beach. The unit was very clean and updated. I would recommend. "
Venice Island / Venice Beach Luxury Villa

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
The price is AED 1,138
AED 3,047 total
includes taxes & fees
23 Feb - 24 Feb
6 BR Heated Pool, Mins from IMG and Anna Maria

Direct Beachfront Gulf with Amazing Views

9.8 out of 10, Exceptional, (90)
"Beautiful location. Quiet, relaxing spot on beach with excellent sunsets every evening. The condo is comfortable and well appointed. "
Direct Beachfront Gulf with Amazing Views

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!

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

"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath

10.0 out of 10, Exceptional, (9)
"The house is beautiful, beds are comfortable, kitchen is stocked beautifully!The pool is definitely on the small side, but our five grandchildren and two adults were all able to be in the pool at the same time and play together.The devastation of the hurricane was still all around us, but the cleanup process was going full speed, and the beach cleanup was very nicely done and still in progress.We were sad some of our favorite restaurants were still closed, but the Waverly restaurant was open and...
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath

Siesta Key Palm Paradise with Heated Saltwater Pool

10.0 out of 10, Exceptional, (11)
"The property was amazing and beautiful. It had everything we needed for a weeks stay. Our stay was interrupted due to a Hurricane. Due to these unforeseen circumstances I did contact the property manager on several occasions and they could not have been more responsive to our needs. "
Siesta Key Palm Paradise with Heated Saltwater Pool

Ground Floor Luxury Villa Steps From Venice Beach

9.2 out of 10, Wonderful, (99)
"The location was great, short walk to beach and downtown. Rooms were spacious and living area was cozy. "
Ground Floor Luxury Villa Steps From Venice Beach

Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room

9.6 out of 10, Exceptional, (71)
"The house was very nice with quiet neighbors. The pool was clean and inviting. All appliances were in working order. There was an issue with the garbage disposal but Gareth was there right away with the tool to fix it so there was no inconvenience. Would definitely stay again. Very nice having 3 king beds!"
Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room

Tropical Oasis Close to Beaches | Pool | Game room

2.0 star property
10.0 out of 10, Exceptional, (2)
"The house was perfect for 2 families including teens and young adults. With 2 master suites, a game room and large screened in lanai, there was plenty of space for everyone to spread out. The home has been beautifully renovated with the latest finishes. We even hosted our extended family for thanksgiving and there was room to seat 20 comfortably. Highly recommend! "
Tropical Oasis Close to Beaches | Pool | Game room

Island Oasis Delights, Pool & Beach

9.8 out of 10, Exceptional, (52)
"This property did not disappoint. The unit we stayed in was so clean with high end furnishings, and everything we needed. The view of the bay , right outside our window, was astonishing. Saw a few other occupants and all were friendly. Very quiet and everyone followed the rules. My only suggestion for improvement would be to repair the dock and refurbish the beach with sand. I hope to return someday. "
Island Oasis Delights, Pool & Beach

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Modern Villa steps away from the white sandy beach on upscale Lido Key, Sarasota

Hemingway Inspired Villa

6.8 out of 10, (5)
"Perfect for us and our 4 legged friends. Friendly and courteous owner. Would book again."
Hemingway Inspired Villa

Casa Blanca Villa B03

9.4 out of 10, Exceptional, (16)
"Excellent"
Casa Blanca Villa B03
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

Tropical Beach Resorts

3.5 star property
9.4 out of 10, Exceptional, (4558)
"property was well kept and room was clean"
The price is AED 940
AED 1,145 total
includes taxes & fees
24 Feb - 25 Feb
Tropical Beach Resorts

Tiny House Siesta

2.0 star property
8.4 out of 10, Very Good, (215)
"Nice little spot close to Siesta Key Beach.Even has an outdoor stage.I like entertaining and it looks like a perfect place to practice.i really did not mind being in the Tiny House it kind of felt like a Hollywood prop.Anyway this is Hollywood and you are in my world.Love is everything."
The price is AED 511
AED 784 total
includes taxes & fees
10 Mar - 11 Mar
Tiny House Siesta

The Ringling Beach House

3.5 star property
9.0 out of 10, Wonderful, (290)
"Could be more clean and updated. Great location!"
The price is AED 983
AED 1,485 total
includes taxes & fees
24 Feb - 25 Feb
The Ringling Beach House
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?
Prices for villas in Osprey range between AED 1,138 and AED 1,138 per night. No matter your budget, you’ll find someplace that suits your needs on Expedia. 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 9.6. Island House Beach Resort V39 is a popular choice with Expedia guests. Travelers staying at this 3-star property can access a barbecue grill and a swimming pool. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another top-rated stay. This 2.5-star villa offers a barbecue grill and a swimming pool, among other conveniences.
How many villas are there in Osprey?
Osprey has 385 villas to choose from. Find your perfect stay quickly and easily by selecting the “Villa” checkbox under the “Property type” tab in our handy filter tool.
Why book your villa in Osprey with Expedia?
With Expedia, it’s a cinch to find your dream villa in Osprey. Getting away with the family? Make the most of our filters to look for stays with amenities like free WiFi. If you have a set budget, choose how much you want to spend and the star rating of the property. We’ll help you find the right place that matches your taste and style.
How can I find cheap villas in Osprey?
The simplest way to track down cheap villas in Osprey is with Expedia’s convenient filter tool. Refine your search results by amenities, star rating and budget to grab unbeatable bargains in only a few keystrokes.