A marina with docked boats, a wooden bridge, and a building with a red roof.

Osprey Village Vacation Rentals

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Our top choices for Osprey Village vacation rentals

1. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,401 reviews)
"We stayed for 2 nights, the location was perfect for our needs! The beds were very comfortable and the kitchen was a added bonus!"
United States
Justine
The price is CA $158
CA $178 total
includes taxes & fees
Aug 19 - Aug 20
Hibiscus Suites - Gateway to Siesta Key

2. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,744 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
The price is CA $188
CA $249 total
includes taxes & fees
Sep 7 - Sep 8
Tropical Beach Resorts

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,295 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is CA $217
CA $269 total
includes taxes & fees
Aug 12 - Aug 13
Captiva Beach Resort

4. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (281 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
The price is CA $213
CA $265 total
includes taxes & fees
Aug 18 - Aug 19
Casey Key Resort

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (662 reviews)
"Perfect beach property. Very clean and affordable for the location!"
United States
Bob
The price is CA $257
CA $290 total
includes taxes & fees
Aug 27 - Aug 28
A Beach Retreat

6. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (383 reviews)
"Great place"
United States
Mario
The price is CA $115
CA $319 total
includes taxes & fees
Aug 12 - Aug 13
Tiny House Siesta

7. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (165 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is CA $287
CA $325 total
includes taxes & fees
Sep 1 - Sep 2
SeaSpray Resort

8. Siesta Heron 7

Siesta Heron 7
3.0 star property
Siesta Key
The price is CA $861
CA $1,487 total
includes taxes & fees
Aug 12 - Aug 13
Siesta Heron 7

9. Siesta Heron Suites & Villas

Siesta Heron Suites & Villas
3.5 star property
Siesta Key
8.6 out of 10, Excellent, (44 reviews)
"Clean rooms, convenient location, nice property and amenities. Simple check-in and check-out"
United States
Christopher Robert
The price is CA $146
CA $445 total
includes taxes & fees
Aug 12 - Aug 13
Siesta Heron Suites & Villas

10. Secluded Cottage - Private BBQ Deck Firepit

Secluded Cottage - Private BBQ Deck Firepit
2.0 star property
Sarasota
The price is CA $104
CA $270 total
includes taxes & fees
Aug 11 - Aug 12
Secluded Cottage - Private BBQ Deck Firepit

11. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (78 reviews)
"Great location, very clean and spacious."
United States
Jason
Siesta Key Island Rentals

12. Explore Sarasota: Condo w/ Pool Access, Near Dtwn

Explore Sarasota: Condo w/ Pool Access, Near Dtwn
3.5 star property
Sarasota
The price is CA $132
CA $400 total
includes taxes & fees
Aug 16 - Aug 17
Explore Sarasota: Condo w/ Pool Access, Near Dtwn

13. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (203 reviews)
"We had a wonderful stay at The Inn on Siesta Key. The Cabana was perfect for our family of 4, very clean and well equipped kitchen. The beds are very comfortable, and we enjoyed our morning coffee on the porch area. The property is fully equipped for the beach with chairs, towels, umbrellas, coolers, ice, and these great wagons to haul it all to the beach. Beaches are a short walk and amazing. The property is also a very short walk to The Village for shopping and dining. Paige checked us in and...
United States
Lisa
The price is CA $319
CA $437 total
includes taxes & fees
Aug 13 - Aug 14
The Inn On Siesta Key

14. Lulu's Key House Loggerhead 2/2 Upstairs

Lulu's Key House Loggerhead 2/2 Upstairs
3.5 star property
Siesta Key Village
Lulu's Key House Loggerhead 2/2 Upstairs

15. Palm Haven at Cape Leyte

Palm Haven at Cape Leyte
2.0 star property
Siesta Key
The price is CA $391
CA $894 total
includes taxes & fees
Aug 11 - Aug 12
Palm Haven at Cape Leyte

16. Cedar Run Resort - Roam Hospitality

Cedar Run Resort - Roam Hospitality
3.5 star property
South Bradenton
9.2 out of 10, Wonderful, (7 reviews)
"The room was very clean and well maintained/new. Staff was friendly and helpful. The air conditioner was great. The room we stayed at had lots of accessories for the beach like chairs and kid’s toys for the beach along with an umbrella. The surroundings are peaceful and beautiful. It was a great experience overall."
United States
Jose Luis Alberti
The price is CA $185
CA $607 total
includes taxes & fees
Aug 11 - Aug 12
Cedar Run Resort - Roam Hospitality

17. Beach Road - Capri

Beach Road - Capri
2.5 star property
Siesta Key
The price is CA $730
CA $952 total
includes taxes & fees
Aug 12 - Aug 13
Beach Road - Capri

18. Coastal Home w Hot Tub Firepit and Music Lounge

Coastal Home w Hot Tub Firepit and Music Lounge
2.0 star property
Siesta Key
The price is CA $497
CA $957 total
includes taxes & fees
Aug 11 - Aug 12
Coastal Home w Hot Tub Firepit and Music Lounge

19. Sun Outdoors Sarasota

Sun Outdoors Sarasota
2.5 star property
Fordville
The price is CA $615
CA $695 total
includes taxes & fees
Aug 17 - Aug 18
Sun Outdoors Sarasota

20. Shoreline Bungalow

Shoreline Bungalow
2.0 star property
Nokomis
The price is CA $171
CA $464 total
includes taxes & fees
Aug 11 - Aug 12
Shoreline Bungalow
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

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.

Frequently asked questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals in Osprey Village close to Nancy's Consignments, or you can go with a more remote option if you're looking for extra privacy while you relax.

What's the top vacation rental that Osprey Village has to offer?

Siesta Key Island Rentals: This vacation home rental near Osprey Village comes with WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

How many vacation rentals will I find in Osprey Village?

Expedia has 3 vacation rentals for your stay in Osprey Village.

What can I see and do in Osprey Village?

While exploring the area, visit family-friendly sights like Nancy's Consignments, or get outside and enjoy nature at Siesta Key Beach. Venice Beach and Lido Beach are other popular places to visit in the area.

What are vacation rentals like in Osprey Village?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Osprey Village. Vacation rentals feature amenities such as patios, hot tubs, and fire pits so you'll be comfy for your stay. If you're concerned about a sanitized environment, vacation rentals can offer a sense of safety away from public hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular option for a family getaway.