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

Osprey Village Holiday Rentals

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Our top choices for Osprey Village holiday rentals

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,760 reviews)
"Clean quiet and close to the beach. Best place for a quiet weekend getaway in a cute quiet beach town"
United States
Lindy
The price is NZ$305
includes taxes & fees
18 Aug - 19 Aug
Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,405 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 NZ$249
includes taxes & fees
16 Aug - 17 Aug
Hibiscus Suites - Gateway to Siesta Key

3. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,297 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
The price is NZ$347
includes taxes & fees
7 Sept - 8 Sept
Captiva Beach Resort

4. 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 NZ$397
includes taxes & fees
12 Sept - 13 Sept
Tiny House Siesta

5. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (665 reviews)
"Lovely place on a family beach."
United States
Robert
The price is NZ$356
includes taxes & fees
27 Aug - 28 Aug
A Beach Retreat

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (166 reviews)
"Beautiful hotel comfortable bed nice and friendly staff!!!!"
United States
Isabel
The price is NZ$378
includes taxes & fees
1 Sept - 2 Sept
SeaSpray Resort

7. Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Sarasota
9.8 out of 10, Exceptional, (8 reviews)
"This was a great stay for us. It was extremely clean and just as described."
United States
Kenzie Q.
The price is NZ$607
includes taxes & fees
15 Aug - 16 Aug
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota

8. Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Southgate
10.0 out of 10, Exceptional, (83 reviews)
"Her stay was outstanding everything was so professionally ready for us we felt at home comfortable the Privacy was impeccable"
United States
James W.
The price is NZ$413
includes taxes & fees
23 Aug - 24 Aug
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.

9. Bright & Beachy–Beach Club Siesta Key 100A by RVA

Bright & Beachy–Beach Club Siesta Key 100A by RVA
South Village
9.0 out of 10, Wonderful, (119 reviews)
"The pool and proximity to the beach are great "
United States
Evan C.
The price is NZ$573
includes taxes & fees
15 Aug - 16 Aug
Bright & Beachy–Beach Club Siesta Key 100A by RVA

10. [lounge like locals] walk to siesta beach +bikes

[lounge like locals] walk to siesta beach +bikes
Siesta Key
9.8 out of 10, Exceptional, (36 reviews)
"Only 10 mins walking from the Village, so easy to check in, great communication, super clean. "
United States
John
The price is NZ$538
includes taxes & fees
19 Aug - 20 Aug
[lounge like locals] walk to siesta beach +bikes

11. Couple’s Escape-Beach Club at Siesta Key 106C by RVA

Couple’s Escape-Beach Club at Siesta Key 106C by RVA
South Village
9.4 out of 10, Exceptional, (105 reviews)
"Great birthday weekend. Awesome location to the beach and nightlife. Highly recommend."
United States
Cindy F.
The price is NZ$559
includes taxes & fees
23 Aug - 24 Aug
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

12. Siesta Key Village-Suite #3: A Block to the Beach!

Siesta Key Village-Suite #3: A Block to the Beach!
Siesta Key Village
9.2 out of 10, Wonderful, (77 reviews)
"We loved this suite. It had everything we needed! "
United States
Danielle F.
The price is NZ$641
includes taxes & fees
16 Aug - 17 Aug
Siesta Key Village-Suite #3: A Block to the Beach!

13. Jetties Pointe Cottage #5 - 408 “Casey Key”

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.8 out of 10, Exceptional, (32 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
The price is NZ$675
includes taxes & fees
16 Aug - 17 Aug
Jetties Pointe Cottage #5 - 408 “Casey Key”

14. Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Ridge Wood Heights
9.4 out of 10, Exceptional, (125 reviews)
"very convenient, it was right in front of the event center that my daughter was dancing."
United States
erica
The price is NZ$486
includes taxes & fees
16 Aug - 17 Aug
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok

15. Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
South Village
8.8 out of 10, Excellent, (89 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
The price is NZ$606
includes taxes & fees
16 Aug - 17 Aug
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach

16. Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
South Village
9.8 out of 10, Exceptional, (34 reviews)
"Great stay."
United States
James J.
The price is NZ$364
includes taxes & fees
17 Aug - 18 Aug
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

17. Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
South Village
9.6 out of 10, Exceptional, (49 reviews)
"We enjoyed our stay alot of stores n restaurants nearby, don’t need to use the car. "
United States
maureen p.
The price is NZ$431
includes taxes & fees
18 Aug - 19 Aug
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

18. Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
South Village
9.4 out of 10, Exceptional, (38 reviews)
"It was a great location with easy access to the pool, beach and entertainment! The place was clean and nice, perfect for our family!"
United States
Emily
The price is NZ$1,008
includes taxes & fees
19 Aug - 20 Aug
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key

19. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
The price is NZ$804
includes taxes & fees
27 Aug - 28 Aug
2BR Beach Style w Pool Beach Club Siesta 204C RVA

20. Beachside Studio Located Across from Main Beach and Half Mile to Village

Beachside Studio Located Across from Main Beach and Half Mile to Village
Sarasota
8.8 out of 10, Excellent, (169 reviews)
"The rental had everything promised. The bed and couch were very comfortable. Everything was clean. Beach access was great. The chairs, cooler, and canopy were were just what was needed to maximize our enjoyment on a great beach."
United States
Karen G.
The price is NZ$459
includes taxes & fees
16 Aug - 17 Aug
Beachside Studio Located Across from Main Beach and Half Mile to Village
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 holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osprey Village holiday 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. 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 holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osprey Village. 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 Osprey Village. 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 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 holiday 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 Osprey Village short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Osprey Village?

Yes, there are holiday rentals in Osprey Village close to Nancy's Consignments, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osprey Village has to offer?

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

How many holiday rentals will I find in Osprey Village?

Expedia has 3 holiday 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 holiday rentals like in Osprey Village?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osprey Village. Holiday rentals offer extras such as laundry facilities and kitchens so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of safety away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular choice for a family trip.