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. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,916 reviews)
"Amazing resort,"
United States
kurt
The price is CA $191
CA $253 total
includes taxes & fees
Sep 27 - Sep 28
Tropical Beach Resorts

2. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,453 reviews)
"This place was perfect!"
United States
Kat
The price is CA $156
CA $176 total
includes taxes & fees
Sep 29 - Sep 30
Hibiscus Suites - Gateway to Siesta Key

3. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (386 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
The price is CA $91
CA $294 total
includes taxes & fees
Oct 8 - Oct 9
Tiny House Siesta

4. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,309 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
The price is CA $208
CA $259 total
includes taxes & fees
Sep 27 - Sep 28
Captiva Beach Resort

5. Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.4 out of 10, Exceptional, (81 reviews)
"The property was clean and had great decor! They provide everything you need for the beach and the pool is a great added bonus. Perfect location with being so close the restaurants and the beach. We are already planning our next stay!"
United States
Meghan
The price is CA $137
CA $449 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Island Rentals

6. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (181 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
The price is CA $300
CA $339 total
includes taxes & fees
Sep 28 - Sep 29
SeaSpray Resort

7. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (683 reviews)
"Great stay!!"
United States
Genghis
The price is CA $266
CA $301 total
includes taxes & fees
Sep 29 - Sep 30
A Beach Retreat

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

Siesta Key, Sea Horse Villa, Pool. Daily rentals
South Village
9.4 out of 10, Exceptional, (54 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.
The price is CA $151
CA $378 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key, Sea Horse Villa, Pool. Daily rentals

9. 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 CA $151
CA $378 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

10. 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 CA $227
CA $398 total
includes taxes & fees
Oct 11 - Oct 12
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.

11. 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)
"Great stay"
United States
Allison H.
The price is CA $209
CA $546 total
includes taxes & fees
Sep 28 - Sep 29
Siesta Key Village-Suite #3: A Block to the Beach!

12. Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
The price is CA $141
CA $424 total
includes taxes & fees
Sep 30 - Oct 1
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

13. 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 CA $210
CA $466 total
includes taxes & fees
Sep 29 - Sep 30
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

14. Siesta beach....one and only

Siesta beach....one and only
Sarasota
9.4 out of 10, Exceptional, (219 reviews)
"The host was very communicative and responsive. The pool was a big hit for our family. Comfy beds and a convenient drive to the beach and other venues. Would definitely stay here again. "
United States
Jennifer M.
The price is CA $171
CA $621 total
includes taxes & fees
Sep 27 - Sep 28
Siesta beach....one and only

15. [escape to paradise] siesta key beach getaway

[escape to paradise] siesta key beach getaway
Siesta Key
9.8 out of 10, Exceptional, (34 reviews)
"Very clean and great location! Beds very comfortable and owner very responsive and accommodating! Highly recommend staying here!"
United States
Tim T.
The price is CA $116
CA $413 total
includes taxes & fees
Sep 29 - Sep 30
[escape to paradise] siesta key beach getaway

16. Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
South Village
8.8 out of 10, Excellent, (89 reviews)
"Great location and easy access to the beach."
United States
Erica B.
The price is CA $226
CA $487 total
includes taxes & fees
Sep 29 - Sep 30
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental

17. Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾

Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾
Central Sarasota
9.6 out of 10, Exceptional, (75 reviews)
"Place was very nice and welcoming we will be back !!!!"
United States
Sue R.
The price is CA $125
CA $474 total
includes taxes & fees
Sep 28 - Sep 29
Tropical 🌴 private, 💯 walkable,⛱️ beach chairs n towels, W&D, park on property 🎾

18. 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 CA $214
CA $445 total
includes taxes & fees
Sep 26 - Sep 27
Bright & Beachy–Beach Club Siesta Key 100A by RVA

19. Heart of Village: Dog-Friendly w/ Pool & Parking

Heart of Village: Dog-Friendly w/ Pool & Parking
Siesta Key Village
9.2 out of 10, Wonderful, (16 reviews)
"Love the place. Perfect location. Close to village, close to beach. Highly suggest and will definitely be back in the future. Host was very friendly and accommodating."
United States
Jeffrey B.
The price is CA $151
CA $503 total
includes taxes & fees
Sep 29 - Sep 30
Heart of Village: Dog-Friendly w/ Pool & Parking

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, (170 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.
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

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, cottages, cabins, villas... 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osprey Village vacation rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osprey Village vacation rentals we have selected for you start as low as CA $176 per night. Entering your travel dates in the search wizard 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.