Osprey Village Vacation Rentals
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Our top choices for Osprey Village vacation rentals
1. Tropical Beach Resorts
Tropical Beach ResortsSouth Village
9.4 out of 10, Exceptional, (6,054 reviews)
"Great resort and location!"
Christine
The price is CA $204
CA $267 total
includes taxes & fees
Nov 10 - Nov 11
2. Hibiscus Suites - Gateway to Siesta Key
Hibiscus Suites - Gateway to Siesta KeySarasota
8.8 out of 10, Excellent, (2,481 reviews)
"This place was perfect!"
Kat
The price is CA $189
CA $214 total
includes taxes & fees
Nov 10 - Nov 11
3. A Beach Retreat
A Beach RetreatCasey Key
9.2 out of 10, Wonderful, (700 reviews)
"Enjoyed our stay"
Robin
The price is CA $260
CA $294 total
includes taxes & fees
Dec 6 - Dec 7
4. Captiva Beach Resort
Captiva Beach ResortSouth Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
Andriy
The price is CA $218
CA $270 total
includes taxes & fees
Nov 10 - Nov 11
5. Casey Key Resort
Casey Key ResortCasey Key
8.4 out of 10, Very good, (288 reviews)
"My boyfriend and I had a wonderful time. Easy late check in. Nice clean room. Property beautiful. Private beach beautiful. We definitely plan to come back and have family join."
Jamie
The price is CA $276
CA $339 total
includes taxes & fees
Dec 10 - Dec 11
6. SeaSpray Resort
SeaSpray ResortSiesta Key
9.6 out of 10, Exceptional, (208 reviews)
"The room was clean and the staff were very kind."
Geraldine
The price is CA $301
CA $340 total
includes taxes & fees
Nov 18 - Nov 19
7. Siesta Heron Suites & Villas
Siesta Heron Suites & VillasSiesta Key
8.4 out of 10, Very good, (46 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
Christopher Robert
The price is CA $132
CA $434 total
includes taxes & fees
Nov 10 - Nov 11
8. Tiny House Siesta
Tiny House SiestaSarasota
8.4 out of 10, Very good, (392 reviews)
"It's a very cute tiny house in a great location. Walking distance to Siesta Keys beach and numerous restaurants. I loved the decor in the sea turtle house. I would definitely stay here again next time I'm in Florida."
Staci
The price is CA $86
CA $287 total
includes taxes & fees
Nov 22 - Nov 23
9. Kon Tiki Inn
Kon Tiki InnVenice Island
10.0 out of 10, Exceptional, (320 reviews)
"Debbie and Sean are excellent hosts. Very clean, very comfortable, very quiet. Pet friendly, which is awesome also. Great location also just a couple miles from downtown or the beach.."
Joseph
The price is CA $230
CA $260 total
includes taxes & fees
Nov 10 - Nov 11
10. The Inn On Siesta Key
The Inn On Siesta KeySiesta Key
10.0 out of 10, Exceptional, (213 reviews)
"Thank you Paige & Gabe! My husband & I had a wonderful stay last week in The Nook at your beautiful Inn. Absolutely loved the old Florida charm and perfect location. Your Inn is immaculately kept as well as comfortable. We especially loved our private patio with the fire pit at The Nook. The location of The Inn could not be more perfect being less than a 5 minute walk across the street to Siesta Key beach as well as a short 10 minute walk to town with all the restaurants & shops. Thanks again...
Karen Jean
The price is CA $323
CA $453 total
includes taxes & fees
Nov 10 - Nov 11
11. 4 Mi to Siesta Key Beach: Condo w/ Pool Access
4 Mi to Siesta Key Beach: Condo w/ Pool AccessSarasota
10.0 out of 10, Exceptional, (1 review)
"The property was clean and decorated so cute. It was easy to find and simple check in. We had a problem with the ac and they fixed it right away. The host was great and communicated very well. Highly recommended!"
Lori
The price is CA $134
CA $425 total
includes taxes & fees
Nov 10 - Nov 11
12. Beach Tree Cottage,Walk To Beach& Siesta
Beach Tree Cottage,Walk To Beach& SiestaSiesta Key Village
The price is CA $153
CA $493 total
includes taxes & fees
Nov 10 - Nov 11
13. Yellow Palm Cottage, Heart of Siesta Key
Yellow Palm Cottage, Heart of Siesta KeySiesta Key Village
The price is CA $249
CA $656 total
includes taxes & fees
Nov 10 - Nov 11
14. Beach View 100ft To Beach and SPA
Beach View 100ft To Beach and SPASiesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is CA $224
CA $572 total
includes taxes & fees
Nov 11 - Nov 12
15. BlueDolphin Cottage Walk To Siesta Beach
BlueDolphin Cottage Walk To Siesta BeachSiesta Key Village
The price is CA $249
CA $641 total
includes taxes & fees
Nov 10 - Nov 11
16. Pineapple Paradise 1 13 min to Beach Fire Pit
Pineapple Paradise 1 13 min to Beach Fire PitCentral Sarasota
The price is CA $215
CA $565 total
includes taxes & fees
Nov 10 - Nov 11
17. Sun Outdoors Sarasota
Sun Outdoors SarasotaFordville
The price is CA $615
CA $694 total
includes taxes & fees
Nov 10 - Nov 11
18. Beach Road
Beach RoadSiesta Key
The price is CA $917
CA $1,273 total
includes taxes & fees
Dec 10 - Dec 11
19. Unwind Poolside + Walk to Beach! Sarasota Retreat
Unwind Poolside + Walk to Beach! Sarasota RetreatSouth Village
8.0 out of 10, Very good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
Eleuterio
The price is CA $384
CA $864 total
includes taxes & fees
Nov 23 - Nov 24
20. 4 Mi to Dtwn! Studio w/ Screened Porch in Sarasota
4 Mi to Dtwn! Studio w/ Screened Porch in SarasotaRidge Wood Heights
The price is CA $170
CA $358 total
includes taxes & fees
Nov 10 - Nov 11
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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Top Osprey Village Hotel Reviews
The Ritz-Carlton, Sarasota
8/10 Good
Find out more about Osprey Village
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osprey Village. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
