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

Osprey Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Osprey vacation rentals

A tented accommodation with a bed, a small table, and a hanging plant.

1. Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
10.0 out of 10, Exceptional, (1 review)
$328 nightly
The price is $365
Oct 5 - Oct 6
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
A tent with two chairs and a welcome mat in front.

2. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$328 nightly
The price is $365
Oct 5 - Oct 6
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida
A room with two beds, each with a black metal frame, white bedding, and striped pillows. There is a small table with a plant, a sign that says 'HAPPY CAMPING,' and a wooden floor.

3. Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$328 nightly
The price is $365
Oct 5 - Oct 6
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tented accommodation with a bed, a small table, a chair, and a refrigerator.

4. Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$328 nightly
The price is $365
Oct 5 - Oct 6
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A compact living space with a kitchen, a dining area, and a sofa with cushions.

5. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (387 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
Oct 8 - Oct 9
Total with taxes and fees
Tiny House Siesta
A pool area with a waterfall feature, lounge chairs, and palm trees.

6. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,934 reviews)
"Amazing resort,"
United States
kurt
$158 nightly
The price is $179
Oct 4 - Oct 5
Total with taxes and fees
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

7. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,456 reviews)
"This place was perfect!"
United States
Kat
$127 nightly
The price is $144
Oct 2 - Oct 3
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A modern kitchen with a stainless steel sink, a dining area with a table and chairs, and a living room with a sofa and a TV.

8. Oceanfront home

Oceanfront home
Vamo
9.8 out of 10, Exceptional, (93 reviews)
"It looks just like the pictures and the sunset daily is absolutely gorgeous. The neighborhood is nice and the people are kind. We loved being short car rides away from stores, beaches and the legacy trail. The owners had great communication. Would definitely stay again."
United States
Ashley H.
$546 nightly
The price is $609
Oct 3 - Oct 4
Total with taxes and fees
Oceanfront home
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

9. Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,314 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$177 nightly
The price is $197
Oct 6 - Oct 7
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.

10. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (686 reviews)
"Great stay!!"
United States
Genghis
$210 nightly
The price is $237
Oct 4 - Oct 5
Total with taxes and fees
A Beach Retreat
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.

11. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (186 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
$234 nightly
The price is $265
Oct 20 - Oct 21
Total with taxes and fees
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

12. Casey Key Resort

Casey Key Resort
3.0 star property
Casey Key
8.4 out of 10, Very good, (284 reviews)
"Nice little property,very well kept.Host was very nice and helpful.Will be back again."
United States
Greg
$236 nightly
The price is $264
Oct 2 - Oct 3
Total with taxes and fees
Casey Key Resort
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

13. 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.
$305 nightly
The price is $340
Oct 2 - Oct 3
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

14. 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.
$297 nightly
The price is $331
Oct 2 - Oct 3
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

15. Romantic Getaway Beach Club Siesta 202B by RVA

Romantic Getaway Beach Club Siesta 202B by RVA
South Village
8.8 out of 10, Excellent, (57 reviews)
"Peaceful getaway. Throughly enjoyed the stay. "
United States
Anonymous traveler
$318 nightly
The price is $355
Oct 2 - Oct 3
Total with taxes and fees
Romantic Getaway Beach Club Siesta 202B by RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

16. 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, (90 reviews)
"It was a great experience, definitely would come back."
United States
Alicia
$322 nightly
The price is $359
Oct 2 - Oct 3
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

17. 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)
"Good"
United States
Gelsy
$421 nightly
The price is $469
Oct 2 - Oct 3
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA

Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
South Village
9.0 out of 10, Wonderful, (77 reviews)
"We found this property to be delightful. We loved the balcony for enjoying our evenings. I would have liked to see a table on the balcony for eating at, it is FL, and I wanted to sit outside for my meals. It was a very close walk to the beach, the pool and hot tub were in excellent working condition. We enjoyed the property. We had a problem, but they had maintenance there within an hour to fix it, I call that a win for the property. "
United States
Jackie J.
$422 nightly
The price is $471
Oct 2 - Oct 3
Total with taxes and fees
Dream Sunsets & Coastal Bliss–Beach Club 108A / RVA
A beach with clear turquoise water and gentle waves.

19. 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.
$263 nightly
The price is $293
Oct 4 - Oct 5
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. 2BR Beach & Trolley–Beach Club Siesta 204B by RVA

2BR Beach & Trolley–Beach Club Siesta 204B by RVA
South Village
8.6 out of 10, Excellent, (48 reviews)
"Excellent"
United States
Yamila
$416 nightly
The price is $464
Oct 2 - Oct 3
Total with taxes and fees
2BR Beach & Trolley–Beach Club Siesta 204B by 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 Hotel Reviews

Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

8/10 Good
"Great property, well managed, and the staff was more than accommodating. I’ll stay here again.! Thank you."
Brian 2-night trip
Posted 1 hour ago
Casey Key Resorts - Mainland

Find out more about Osprey

Everything you need to know about Osprey 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 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osprey vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osprey. 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 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 $144 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 rentals

At Expedia, we put the best Osprey 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 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 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. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Osprey?

Yes, we have vacation rentals in Osprey near Jim Neville Marine Preserve, or you can go with a more secluded option if you're looking for extra privacy while you relax. Visitors to Osprey speak positively about the popular beaches and top-notch restaurants in this destination. While you're in the area, you can also enjoy the lively bars and shops.

What are some of the best vacation rentals in Osprey?

Tropical Villas of Venice Beach: This vacation home rental near Osprey 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 are there in Osprey?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Osprey stay.

What’s there to see and do in Osprey?

Turtle Beach and Nokomis Beach are a couple of scenic spots to enjoy the outdoors, whereas Historic Spanish Point is one of the cultural attractions. While in the area, you can also visit popular places like Siesta Key Beach and Lido Beach.

What’s a vacation rental in Osprey like?

Vacation rentals are private properties you can stay in for a long or short time in Osprey. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have all the comforts of home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of security away from shared hotel elevators and lobbies packed with people while still allowing you the enjoyment of travel. You'll also have more space in a vacation rental than in a hotel, which makes a vacation rental an attractive option for families.