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

Osprey Village Vacation Rentals

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Check prices for these dates

In two weeks
Aug 28 - Aug 30
In two months
Oct 9 - Oct 11
In three months
Nov 6 - Nov 8
In four months
Dec 4 - Dec 6

Our top choices for Osprey Village vacation rentals

Property grounds

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,762 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 ￥20,621
￥27,443 total
includes taxes & fees
Aug 18 - Aug 19
Tropical Beach Resorts
Outdoor pool, a heated pool, open 7:00 AM to 8:00 PM, sun loungers

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,406 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 ￥18,002
￥20,342 total
includes taxes & fees
Aug 18 - Aug 19
Hibiscus Suites - Gateway to Siesta Key
Front of property - evening/night

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 ￥26,269
￥32,384 total
includes taxes & fees
Aug 17 - Aug 18
Captiva Beach Resort
Cabin (Tiny House - The Siesta) | Living area | Flat-screen TV, Netflix, streaming services

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 ￥13,181
￥36,498 total
includes taxes & fees
Aug 20 - Aug 21
Tiny House Siesta
Beachside One Bedroom Suite | Premium bedding, pillowtop beds, iron/ironing board (on request)

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 ￥29,358
￥33,175 total
includes taxes & fees
Sep 10 - Sep 11
A Beach Retreat
Superior Suite, 2 Bedrooms | In-room safe, iron/ironing board, WiFi (free)

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 ￥30,866
￥34,879 total
includes taxes & fees
Sep 1 - Sep 2
SeaSpray Resort
Coffee/tea maker, fridge, microwave, oven

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.
Resort-Style 2-Bedroom Townhome with Pool, WiFi, and AC in Sarasota
Coffee/tea maker, fridge, microwave, oven

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, (84 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 ￥11,338
￥39,803 total
includes taxes & fees
Aug 23 - Aug 24
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
Beach nearby, beach umbrellas

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 ￥25,332
￥54,846 total
includes taxes & fees
Aug 20 - Aug 21
Bright & Beachy–Beach Club Siesta Key 100A by RVA
Coffee/tea maker, fridge, microwave, oven

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 ￥16,261
￥50,780 total
includes taxes & fees
Aug 17 - Aug 18
[lounge like locals] walk to siesta beach +bikes
Beach nearby, beach umbrellas

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 ￥24,217
￥53,338 total
includes taxes & fees
Aug 20 - Aug 21
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
Beach nearby, sun loungers, beach towels

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 ￥22,608
￥60,360 total
includes taxes & fees
Aug 22 - Aug 23
Siesta Key Village-Suite #3: A Block to the Beach!
On 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 ￥26,075
￥63,672 total
includes taxes & fees
Aug 16 - Aug 17
Jetties Pointe Cottage #5 - 408 “Casey Key”
A heated pool

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 ￥24,695
￥45,446 total
includes taxes & fees
Sep 10 - Sep 11
Siesta Key Master suite 1 Lg BR & 1 large bonus rm w bed Heated Pool & Pets ok
Beach nearby, beach umbrellas

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 ￥27,562
￥57,861 total
includes taxes & fees
Aug 18 - Aug 19
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
Beach nearby

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 ￥15,328
￥34,324 total
includes taxes & fees
Aug 17 - Aug 18
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
Beach nearby

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 ￥15,328
￥40,687 total
includes taxes & fees
Aug 18 - Aug 19
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
Beach nearby, sun loungers, beach towels, snorkeling

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 ￥26,073
￥93,607 total
includes taxes & fees
Aug 19 - Aug 20
Beach Club | Renovated Condo | Steps to Crescent Beach | Heated Pool & Hot Tub | Siesta Key
Beach nearby

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 ￥31,705
￥75,585 total
includes taxes & fees
Aug 16 - Aug 17
2BR Beach Style w Pool Beach Club Siesta 204C RVA
Beach nearby

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 ￥23,591
￥43,297 total
includes taxes & fees
Aug 16 - Aug 17
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

Hyatt Place Sarasota/Bradenton Airport

Hyatt Place Sarasota/Bradenton Airport

10/10 Excellent
"Our experience was 100%. We booked through a third party. We got a room upgrade. The staff was amazing. Our room was flawless. Such a great experience."
andrea 1-night trip
Posted 3 hours ago
Hyatt Place Sarasota/Bradenton Airport

Find out more about Osprey Village

Search for holiday rentals in Osprey Village on Expedia! You can easily find your home rentals, villas, holiday apartments in Osprey Village using one of the methods below:

  • View our selection of featured holiday rentals in Osprey Village
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Look no further and take a look at our great range of rental properties in Osprey Village!

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.