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Compare 375 Villas in Osprey with updated reviews, rates, and availability.

Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
9.8 out of 10, Exceptional, (90)
"My husband and I have stayed at a dozen or more VRBOs across the state of Florida. Our most recent stay was probably one of our most favorite to date! The private beach access was perfect, and the beach was beautiful. The condo was clean, neat, tidy, and had all of the amenities one could ask for. Access to the condo was easy, and the owners were quick to respond with questions."
Beach, Sand, Sunsets. . . Rocking chair in front of the porch!
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
9.8 out of 10, Exceptional, (79)
"Excellent location close to the beach and the village. The property was outdated but clean and well-stocked. We had a great time!"
Siesta Key 2BR /1Bath Villa Barefoot Bungalows -“Cozy” 1000 ft from beach.
Direct Beachfront Gulf with Amazing Views
9.8 out of 10, Exceptional, (86)
"Loved the condo at Longboat Key. It was perfect for our visit to Florida. Angel gave us a little bit earlier check in. We did have a small issue upon arrival, but Angel was very quick to reply and work on getting the situation remedied. We had a very pleasant stay in LBK."
Direct Beachfront Gulf with Amazing Views
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Completely Remodeled- 150 Yards to Beach and Restaurants!
10.0 out of 10, Exceptional, (23)
"We really appreciated having two outdoor sitting areas. There was the back patio with very comfortable cushions and an umbrella, and when it rained, we enjoyed the chairs in the front as well. The beach equipment was the best!!! We were so grateful for new chairs, umbrella, and wagon. Access to the perfect beach and pool could not have been easier. Everything was so very convenient...no car necessary...and we love the trolley and the stop...just a few steps from our door. "
Completely Remodeled- 150 Yards to Beach and Restaurants!
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
10.0 out of 10, Exceptional, (121)
"This is a beautiful and spacious house. Less than a half mile to the beach, so we walked each time. This gave us the opportunity to see a lot of wildlife along the intercostal. The house had everything we needed for the week. We would definitely stay here again."
Top Rated Villa For Rent! Short Walk To Beach. Swimming Pool. Family-Friendly
Luxury Villa steps from Venice Beach Children friendly
9.4 out of 10, Exceptional, (93)
"I recently spent four days and three nights at a property in Venice Beach, FL, and overall, it was a memorable experience with my family celebrating my dad's 73rd birthday. The location was fantastic, with just a five-minute walk to the beach, making it convenient for us to soak up the sun and enjoy the ocean breeze. Unfortunately my dad was not able to make this short walk. However, there was a public parking available right at the beach entrance. We would just drive him over to enjoy the...
Luxury Villa steps from Venice Beach Children friendly
Island Oasis Delights
9.8 out of 10, Exceptional, (47)
"Property is lovely, well appointed decor. Lots of storage. Comfortable bed. Loved this place. Will definitely return!"
Island Oasis Delights
Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room
9.6 out of 10, Exceptional, (65)
"Gareth and Eileen are very responsive! Perfect home for our trip. The location was great. We have no complaints at all. Having the pool was a bonus. We will definitely book again in the future."
Luxury home 3 King suites,private setting, pool,1 mile to beach wi-fi,games room
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
8.6 out of 10, Excellent, (71)
"Loved it all! Beds were comfortable, everything was well stocked or supplied. Very clean and perfect for anyone wanting to stay near a great beach! Loved the book of suggestions and easy instructions on TV and everything else."
The price is AED 327
AED 978 total
includes taxes & fees
8 Jul - 9 Jul
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. SmartTV, Full Kitchen
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
Charming 3 bd 2 ba villa in cool Bradenton. WiFi AC laundry lanai community pool
Waterfront Paradise Bay
10.0 out of 10, Exceptional, (73)
"Everything was clean and comfortable, good tips to explore the area, great location."
Waterfront Paradise Bay
Beautiful 3 Bedroom 2 Bath, With A Quick Walk to Siesta Beach!
Beautiful 3 Bedroom 2 Bath, With A Quick Walk to Siesta Beach!
2 Minute Walk to Siesta Beach (really!!) Great value, great location !!!
9.8 out of 10, Exceptional, (54)
"This is a great place to stay close to the beach and local shops. Owner was great to deal with and everything was clean. Had a great stay, only wish it was longer!"
2 Minute Walk to Siesta Beach (really!!) Great value, great location !!!
Jamaica Royale #11- 3 Heated Pools, Walk to Beach!
10.0 out of 10, Exceptional, (1)
"Everything's awesome about this property and location, we spent 1 week and had a great time, we didn't want to leave"
Jamaica Royale #11- 3 Heated Pools, Walk to Beach!
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. Cable TV, Full Kitchen
9.0 out of 10, Wonderful, (107)
"The property was just what we were looking for. The location is great. It is a perfect place to stay to walk to restaurants and the beach. The shower was the best shower i have ever used, and towels were luxurious. The host was friendly. We wiuld definitely stay here again."
The price is AED 327
AED 978 total
includes taxes & fees
15 Jul - 16 Jul
Walk to Nokomis Beach. Quality, Cleanliness, Affordable. Cable TV, Full Kitchen
Beautifully Updated Villa Directly on Crescent Beach
9.8 out of 10, Exceptional, (51)
"Well... We liked the property... the only thing that we were really confused about that it says the unit was recently "updated"... a few outlets need replacing... the fridge/freezer NEEDS to be upgraded...ice maker doesnt work and had needed cleaning a long time ago..the washing machine kept getting stuck on "rinse" cycle...beach umbrellas are all not working properly or broken...the 2 beach coolers provided were Styrofoam and old and moldy....not many beach items to use (no kart...
Beautifully Updated Villa Directly on Crescent Beach
Cozy Condo on Siesta Key with Beach and Pool Access!
Cozy Condo on Siesta Key with Beach and Pool Access!
Newly Remodeled-150 Yards to Beach and Restaurants!
10.0 out of 10, Exceptional, (30)
"Perfect location. John responded quickly to any questions we had. We would definitely return! Thanks for a great time!"
The price is AED 643
AED 1,465 total
includes taxes & fees
16 Jul - 17 Jul
Newly Remodeled-150 Yards to Beach and Restaurants!
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
9.8 out of 10, Exceptional, (9)
"The property was as described. The owners were responsive. I appreciated them providing essentials (soap, toilet paper, and paper towels)."
Clean & Modern, Close to Beach, Restaurants, Downtown SRQ!
Luxurious Private Villa,Heated pool, walk to beach,2 King suites,Free wi fi
9.6 out of 10, Exceptional, (92)
"Fabulous house and layout! Great location and close to the beach! Enjoyed our time relaxing in the pool! Close to many stores and restaurants! Hope to return soon!"
Luxurious Private Villa,Heated pool, walk to beach,2 King suites,Free wi fi
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See all available properties in Osprey
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.

Other property types in Osprey

Tropical Beach Resorts
3.5 star property
9.4 out of 10, Exceptional, (4436)
"Great area!"
The price is AED 534
AED 672 total
includes taxes & fees
8 Jul - 9 Jul
Tropical Beach Resorts
Hibiscus Suites - Gateway to Siesta Key
2.5 star property
8.6 out of 10, Excellent, (2026)
"Clean, quiet, convenient! Staff, especially Jake, are extremely friendly and helpful. If you want a nice place in a great location this is perfect. We had our own kitchen very close to everything you need. "
The price is AED 444
AED 490 total
includes taxes & fees
8 Jul - 9 Jul
Hibiscus Suites - Gateway to Siesta Key
Captiva Beach Resort
2.0 star property
9.0 out of 10, Wonderful, (1042)
"Would recommend this place to others. Good price for so close to the Siesta Key Beach. "
The price is AED 553
AED 735 total
includes taxes & fees
8 Jul - 9 Jul
Captiva Beach Resort
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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