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Compare 390 Villas in Osprey with updated reviews, rates, and availability.

Waterfront Mermaid's Retreat Delights!
FREE Shared use of our 2 Kayaks to explore Picturesque Lemon Bay! (life jackets required) (adults only on kayaks) Dolphins often spotted!

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!
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
The beach view from the front porch

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

10.0 out of 10, Exceptional, (103)
"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!
Waterfront Villa Seaglass
Living area

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
Large Living Space with HD Flat Screen TV, Cable, DVD Player and Wi-Fi

Venice Island / Venice Beach Luxury Villa

9.4 out of 10, Exceptional, (110)
"Cozy apartment close to beach and downtown "
Venice Island / Venice Beach Luxury Villa
"Pelican Nest"Private Beach & Bay access & Pool 4bedroom 3bath
Exterior

"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
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!
Immaculate Villa with heated pool & spa-Min to Beach-resort inspired amenities
Enjoy this very private custom pool and spa-water features-lights- bubblers

Immaculate Villa with heated pool & spa-Min to Beach-resort inspired amenities

10.0 out of 10, Exceptional, (45)
" We had an amazing stay at this house close to the beach! It was beautifully decorated. The cleanliness of the home was impressive, and we truly appreciated the stunning swimming pool, it was a great spot to relax. The kitchen was a dream, equipped with every gadget you could possibly need, the cabinets were clearly marked for easy access. We loved that the garage had beach chairs, an umbrella, a wagon for convenience, beach toys ,as well as a sifter basket for shark tooth hunting! The owner was...
Immaculate Villa with heated pool & spa-Min to Beach-resort inspired amenities
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
Exterior

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
6 BR Heated Pool, Mins from IMG and Anna Maria

6 BR Heated Pool, Mins from IMG and Anna Maria

3.0 star property
6 BR Heated Pool, Mins from IMG and Anna Maria
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
Cozy located on first floor in this 1946 Triplex. 2 BR 1 BA each king size beds

Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.

9.8 out of 10, Exceptional, (86)
"Lisa is great to rent from "
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
Island Oasis Delights, Pool & Beach
Breathtaking sunrises!

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
Updated Downtown Sarasota Villa, 2b/2b

Updated Downtown Sarasota Villa, 2b/2b

10.0 out of 10, Exceptional, (2)
"I had a great experience whit my family, we really enjoyed. "
The price is AED 422
AED 1,076 total
includes taxes & fees
12 Jan - 13 Jan
Updated Downtown Sarasota Villa, 2b/2b
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
The entrance to your vacation villa.

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
Siesta Key Palm Paradise with Heated Saltwater Pool
Saltwater Pool, heating optional.

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
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!

Perfect Getaway Villa with 2 bedrooms / 2 baths, quick walk to the beach!
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
Sarasota Vacation Rental Villa | 2BR | 2BA | Step-Free Access

Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!

10.0 out of 10, Exceptional, (12)
"Had everything we needed for an enjoyable & relaxing visit."
Sarasota Villa w/ Pool Access ~ 4 Mi to Beach!
Walk to Beach & Historic Downtown Venice - Rennovated 2 Bed, 2.5 Ba, off-st pkg
Dining

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
Villa Bookelia - 4 Bedroom Pool Home by Gulfcoast Holiday Homes
Pool

Villa Bookelia - 4 Bedroom Pool Home by Gulfcoast Holiday Homes

9.4 out of 10, Exceptional, (43)
"House was perfect for the amount of people we had. Pool was great. Close to stores."
Villa Bookelia - 4 Bedroom Pool Home by Gulfcoast Holiday Homes
Beautiful Remodeled 2br 2b beachside Villa at Horizons West A-9
Exterior

Beautiful Remodeled 2br 2b beachside Villa at Horizons West A-9

Beautiful Remodeled 2br 2b beachside Villa at Horizons West A-9
Paradise Cove at Lemon Bay
Exterior

Paradise Cove at Lemon Bay

3.5 star property
8.0 out of 10, Very Good, (73)
"Excellent stay. The unit is well furnished, with many lovely details (bath robe, bedspread on the couch, etc.), is clean and has everything you need. The mattress is comfortable. The place was completely cleaned up and fixed so soon after the storms. Liked evenings by the water and watching the sunset."
Paradise Cove at Lemon Bay
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
Outdoor pool

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. "
The price is AED 534
AED 686 total
includes taxes & fees
13 Jan - 14 Jan
Tropical Beach Resorts
The Residences at Siesta Key Beach by Hyatt Vacation Club
Exterior

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 star property
9.8 out of 10, Exceptional, (220)
"Very lovely (and large!) accommodation. Extremely clean. Front desk staff kind of rude/pretentious.Great location right on the beach at Siesta Key. Heated pool with good poolside bar. Also had a hot tub, which was nice as the weather was a bit cool when we were there. Feel like I was misled a bit based on room description--thought we were booking a room with beach view, but instead got "city view"--which essentially looked into a back alley and at a 7-eleven. For the price/my personal budget,...
The price is AED 1,875
AED 2,305 total
includes taxes & fees
28 Jan - 29 Jan
The Residences at Siesta Key Beach by Hyatt Vacation Club
Hibiscus Suites - Gateway to Siesta Key
Outdoor pool

Hibiscus Suites - Gateway to Siesta Key

2.5 star property
8.6 out of 10, Excellent, (2085)
"The room was so neat and would definitely recommend anyone needing a one nights stay!! We had a great time! "
The price is AED 547
AED 618 total
includes taxes & fees
16 Jan - 17 Jan
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?
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?
There are multiple villas in Osprey with a total average guest review rating of 9.6. Island House Beach Resort V39 is a hit with travelers. This 3-star stay offers a barbecue grill and a swimming pool. Island House Beach Resort V1 on the beautiful Crescent Beach in Siesta Key is another great option. It has a 2.5-star rating and conveniences such as a swimming pool and a barbecue grill.
How many villas are there in Osprey?
Osprey has 390 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.