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Compare 396 Villas in Osprey with updated reviews, rates, and availability.

Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 6 Minutes to Beaches
10.0 out of 10, Exceptional, (1)
"Cute place located in a historic district in the heart of downtown. I could jog from the house to the waterfront park and enjoy the view on my jog- a big bonus! Loved their welcome book. It had lots of great info about the area. You do have to walk through a bedroom to access the backyard but as one of my kids slept in this room it wasnt a big deal."
Villa & Garden in Downtown Sarasota ~ Walkable to downtown, 6 Minutes to Beaches
Paradise Cove at Lemon Bay
3.5 star property
8.0 out of 10, Very Good, (72)
"Older property but well-kept. Nice little get-away spot. "
Paradise Cove at Lemon Bay
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
10.0 out of 10, Exceptional, (102)
"So it was immediately after Hurricane Helene. Pat kept us updated as we were on the road to the property. The day before we were to arrive Pat called and said option A was out and option B would have too much water. So she refunded all our money including the VRBO fee. Excellent and honest host."
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Luxury Villa steps from Venice Beach Children friendly
9.4 out of 10, Exceptional, (96)
"Short walk to beach, lots of extra things there to help with your stay. Totally enjoyed. "
Luxury Villa steps from Venice Beach Children friendly
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!
Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room
9.6 out of 10, Exceptional, (70)
"We have stayed many times in the area and love it, the house was beautiful and very comfortable. We weren't able to stay the entire week due to Hurricane Milton. Gameroom was not air conditioned, not really practical in south Florida, also trouble with dryer, finally able to resolve."
Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
10.0 out of 10, Exceptional, (1)
"Condo was as listed, community/neighborhood though has way to many rules for a vacation spot. You cant not have noise that goes outside your small area. No noise after 11pm at all which was hard to maintain with 4 kids ranging from 2-11years old on a vacation trip. Beaches stay packed and if you dont arrive by 9am you probably want find parking. If you do arrive early and get a parking spot the beaches literally get so full your shade tents will touch the person next to you your so close. All...
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
Peaceful Beach Home Fully Equipped!
Peaceful Beach Home Fully Equipped!
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!
Ground Floor Luxury Villa Steps From Venice Beach
9.2 out of 10, Wonderful, (95)
"One block away from the beach!!!! Had a minor issue with the property, called the property Manager , very friendly , and she took care of the situation immediately. Walking distance to restaurants, shopping, and fun events. Excellent visit!!!"
Ground Floor Luxury Villa Steps From Venice Beach
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
Venice Island / Venice Beach Luxury Villa
9.4 out of 10, Exceptional, (106)
"The property location was great within walking distance to Venice Beach. Very clean and stocked with necessary items. Property Manager was outstanding. She was in contact with us throughout hurricane Helena. We will definitely be back. "
Venice Island / Venice Beach Luxury Villa
Sunny Gulf Coast Villa: Direct Beach & Pool Access
9.0 out of 10, Wonderful, (25)
"The beach is practically your backyard! Definitely be returning next year! "
Sunny Gulf Coast Villa: Direct Beach & Pool Access
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
10.0 out of 10, Exceptional, (7)
"Absolutely loved our stay. Beautiful place. Tons of room, well furnished, close to beach and restaurants. Excellent communication with the host of you need anything."
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
2 Miles from Siesta Key - Modern Apartment w/ hot tub
9.6 out of 10, Exceptional, (20)
"Awesome experience, host was very fast at communicating 10/10"
2 Miles from Siesta Key - Modern Apartment w/ hot tub
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
8.6 out of 10, Excellent, (74)
"The house was very clean I had a small problem when we got there but was resolved very fast. The owner was there in a matter of minutes."
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
Resort-Style Coastal Villa - Luxurious Courtyard - Splash Pad, Fire Pit, and More!
10.0 out of 10, Exceptional, (1)
Resort-Style Coastal Villa - Luxurious Courtyard - Splash Pad, Fire Pit, and More!
Luxurious Private Villa,Heated pool, walk to beach,2 King suites,Free wi fi
9.6 out of 10, Exceptional, (95)
"great place! Great owner reacted promptly to any issues. Would recommend this to anyone. "
Luxurious Private Villa,Heated pool, walk to beach,2 King suites,Free wi fi
Perfect Getaway Villa with 2 bedrooms / 2 baths, quick walk to the beach!
Perfect Getaway Villa with 2 bedrooms / 2 baths, quick walk to the beach!
Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg
10.0 out of 10, Exceptional, (11)
"My family of 4 had a great stay at Rick’s home. The duplex had everything we needed for our visit. The beach chairs, umbrella, and shark tooth sifter were a huge bonus. Downtown was an easy walk and there is a park at the end of the street that the kids enjoyed. The beach wasn’t walkable for us due to the amount of stuff we had. As others have stated, the neighborhood is nice and quiet."
Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg
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, (4537)
"The stay at the hotel was good. Issue was if you didn’t purchase their chair and umbrella then you were forced to sit at the end where the beach area is not kept nice. You’re spending the same money as everyone else to stay at resort. Should have the same right to sit where you want on the beach. "
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2074)
"Our suite was very clean and the hospitality was wonderful. Would definitely recommend to anyone. If we ever visit the area again we would definitely stay there."
The price is SAR 629
SAR 689 total
includes taxes & fees
15 Nov - 16 Nov
Hibiscus Suites - Gateway to Siesta Key
Kon Tiki Inn
2.0 star property
10.0 out of 10, Exceptional, (167)
"place is so cute and very clean and centrally located for what we needed. Shawn was great and would definately stay again. "
The price is SAR 699
SAR 773 total
includes taxes & fees
17 Nov - 18 Nov
Kon Tiki Inn
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 and 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 9.5. Island House Beach Resort V39 is a popular choice with Expedia guests. Visitors staying at this 3-star property will have access to free internet services and WiFi. Island House Beach Resort V1 On The Beautiful Crescent Beach In Siesta Key is another highly recommended stay. This 2.5-star villa offers a swimming pool and WiFi, among other conveniences.
How many villas are there in Osprey?
Osprey has 396 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.