Osprey Village Vacation Rentals

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Check prices for these dates

In two weeks
Nov 20 - Nov 22
In two months
Jan 1 - Jan 3
In three months
Jan 29 - Jan 31
In four months
Feb 26 - Feb 28

Our top choices for Osprey Village vacation rentals

A pool area with a waterfall feature, lounge chairs, and palm trees.

1. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (6,035 reviews)
"Great resort and location!"
United States
Christine
$166 nightly
The price is $188
Dec 6 - Dec 7
Total with taxes and fees
Tropical Beach Resorts
A compact living space with a kitchen, a dining area, and a sofa with cushions.

2. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (391 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."
United States
Staci
$181 nightly
The price is $205
Nov 18 - Nov 19
Total with taxes and fees
Tiny House Siesta
An outdoor patio with a grill, white chairs, and a red umbrella.

3. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,479 reviews)
"This place was perfect!"
United States
Kat
$152 nightly
The price is $172
Nov 24 - Nov 25
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A modern living room with a flat-screen TV on a wooden cabinet, a grey sofa with patterned cushions, and a large window with sheer curtains.

4. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (206 reviews)
"The room was clean and the staff were very kind."
United States
Geraldine
$204 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

5. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (285 reviews)
"Is was a great place to stay, everything was perfect!"
United States
Tracie Costello
$215 nightly
The price is $240
Dec 2 - Dec 3
Total with taxes and fees
Casey Key Resort
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

6. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,332 reviews)
"We liked the clean room, friendly staff, close to the beach and outdoor amenities."
United States
Andriy
$192 nightly
The price is $215
Nov 8 - Nov 9
Total with taxes and fees
Captiva Beach Resort
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

7. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (697 reviews)
"Enjoyed our stay"
United States
Robin
$205 nightly
The price is $231
Dec 6 - Dec 7
Total with taxes and fees
A Beach Retreat
A pathway with wooden posts and ropes, leading to a building with a sign indicating a nautical room.

8. Kon Tiki Inn

Kon Tiki Inn
2.5 star property
Venice Island
10.0 out of 10, Exceptional, (318 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.."
United States
Joseph
$145 nightly
The price is $164
Nov 19 - Nov 20
Total with taxes and fees
Kon Tiki Inn
A swimming pool with a hot tub area, surrounded by a glass enclosure, and palm trees in the background.

9. The Dolphin

The Dolphin
Nokomis
9.8 out of 10, Exceptional, (21 reviews)
"The cottage was comfortable and the pool was relaxing. "
United States
daniel
$204 nightly
The price is $229
Nov 8 - Nov 9
Total with taxes and fees
The Dolphin
A bedroom with a bed, a dresser, a television, a painting, and a chair.

10. 2 Miles to Siesta Key

2 Miles to Siesta Key
Gulf Gate Estates
10.0 out of 10, Exceptional, (29 reviews)
"Had a great stay! "
United States
Keith K.
$160 nightly
The price is $179
Nov 7 - Nov 8
Total with taxes and fees
2 Miles to Siesta Key
A beach with clear turquoise water and gentle waves.

11. Siesta Key, Sea Horse Villa, Pool. Daily rentals

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (55 reviews)
"Perfect weekend getaway stay for my husband and I! The cottage had everything we needed, was thoroughly cleaned and location was perfect for restaurant hopping and beach going. Would definitely stay again!"
United States
Allie A.
$274 nightly
The price is $307
Nov 7 - Nov 8
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach with a clear sky and calm sea.

12. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta 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...
United States
Karen Jean
$288 nightly
The price is $326
Nov 8 - Nov 9
Total with taxes and fees
The Inn On Siesta Key
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

13. 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.
$262 nightly
The price is $294
Nov 8 - Nov 9
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach scene with a large sandcastle and people around it.

14. Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.8 out of 10, Exceptional, (91 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
$273 nightly
The price is $304
Nov 10 - Nov 11
Total with taxes and fees
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

15. 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.
$232 nightly
The price is $260
Nov 30 - Dec 1
Total with taxes and fees
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
A beach with waves and a bird flying near the shore.

16. Red Lifeguard Stand - pet freindly

Red Lifeguard Stand - pet freindly
Sarasota
9.4 out of 10, Exceptional, (26 reviews)
"Easy to access, close to beach, and easy stay."
United States
Maribel R.
$159 nightly
The price is $178
Nov 8 - Nov 9
Total with taxes and fees
Red Lifeguard Stand - pet freindly
A living room with a red sofa, a glass coffee table, a TV mounted on the wall, and a dining area with a floral tablecloth.

17. Charming cottage for 2 across warm mineral springs park

Charming cottage for 2 across warm mineral springs park
Warm Mineral Springs
9.0 out of 10, Wonderful, (29 reviews)
"Host responded quicklyWould stay again"
United States
VIKTOR M.
$127 nightly
The price is $142
Nov 13 - Nov 14
Total with taxes and fees
Charming cottage for 2 across warm mineral springs park
A kitchen with white cabinets, a granite countertop, stainless steel appliances, and a tiled backsplash.

18. 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)
"The place was super cute, clean, quiet, cozy, and in a great location. The host was very communicative and sweet. Definitely a great stay, 10/10 recommend!"
United States
Sierra B.
$243 nightly
The price is $272
Nov 8 - Nov 9
Total with taxes and fees
Centrally located! 6 miles to Siesta and St. Armands. 2 miles to downtown.
A beach with a small cluster of palm trees in the foreground and a sandy beach extending to the horizon.

19. [Beach Elements] pool view withprivate beach access

[Beach Elements] pool view withprivate beach access
Siesta Key
9.6 out of 10, Exceptional, (45 reviews)
"The space was clean and well-equipped, and the host was easily reachable and responded quickly when I asked a question. The private beach access was nice. I would stay here again. "
United States
Natalie M.
$251 nightly
The price is $256
Nov 9 - Nov 10
Total with taxes and fees
[Beach Elements] pool view withprivate beach access
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. 2BR Beach Style w Pool Beach Club Siesta 204C RVA

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
9.0 out of 10, Wonderful, (81 reviews)
"Beautiful place"
United States
Chad
$367 nightly
The price is $411
Nov 6 - Nov 7
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA
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

A modern breakfast area with labeled dispensers for yogurt, eggs, and milk.
Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG
Nokomis

10/10 Excellent

Good breakfast and great location.
United States
Linda
Reviewed November 4, 2026
Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Find out more about Osprey Village

Everything you need to know about Osprey Village vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osprey Village vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osprey Village vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey Village vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey Village. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osprey Village in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $141 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osprey Village rentals

At Expedia, we put the best Osprey Village vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osprey Village rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osprey Village vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osprey Village. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Frequently Asked Questions

Can I find a vacation rental in Osprey Village?

Yes, we give you a choice of vacation rentals close to popular local attractions in Osprey Village, or you can go with a more secluded option if you're looking for a relaxing stay.

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

Tropical Villas of Venice Beach: This vacation home rental near Osprey Village is located near the beach and has an outdoor pool, a terrace, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a microwave, and kitchenware. Make the most of the garden in this rental home to help you unwind.

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 Mote Marine Laboratory & Aquarium, or get outside and enjoy nature at Siesta Key Beach. Lido Beach and Turtle Beach are a couple of places you'll find in the larger 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.