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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Osprey vacation rentals

A tent with two chairs and a welcome mat in front.

1. Timberline Glamping Sarasota Site 106

Timberline Glamping Sarasota Site 106
Sarasota
$425 nightly
The price is $473
Oct 12 - Oct 13
Total with taxes and fees
Timberline Glamping Sarasota Site 106
A tent with a wooden platform, surrounded by trees and gravel.

2. Timberline Glamping Site 20

Timberline Glamping Site 20
Sarasota
$425 nightly
The price is $473
Oct 13 - Oct 14
Total with taxes and fees
Timberline Glamping Site 20
A tented accommodation with a bed, a small table, and a hanging plant.

3. Timberline Glamping Sarasota Site 19

Timberline Glamping Sarasota Site 19
Sarasota
10.0 out of 10, Exceptional, (1 review)
$425 nightly
The price is $473
Oct 12 - Oct 13
Total with taxes and fees
Timberline Glamping Sarasota Site 19
A grill with a stick over it, a tent, and two chairs in the background.

4. Timberline Glamping Sarasota Site 105

Timberline Glamping Sarasota Site 105
Sarasota
$425 nightly
The price is $473
Oct 12 - Oct 13
Total with taxes and fees
Timberline Glamping Sarasota Site 105
A pool area with a waterfall feature, lounge chairs, and palm trees.

5. Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,962 reviews)
"Amazing resort,"
United States
kurt
$150 nightly
The price is $170
Oct 11 - Oct 12
Total with taxes and fees
Tropical Beach Resorts
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, (1,318 reviews)
"Clean room, beach access, easy parking, friendly staff"
United States
Karla
$167 nightly
The price is $187
Oct 11 - Oct 12
Total with taxes and fees
Captiva Beach Resort
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, (2,465 reviews)
"This place was perfect!"
United States
Kat
$127 nightly
The price is $144
Oct 11 - Oct 12
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key
A compact living space with a kitchen, a dining area, and a sofa with cushions.

8. 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
$180 nightly
The price is $203
Oct 15 - Oct 16
Total with taxes and fees
Tiny House Siesta
A living room with a view of the ocean, a ceiling fan, and a wooden coffee table.

9. A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (688 reviews)
"Great stay!!"
United States
Genghis
$205 nightly
The price is $231
Nov 4 - Nov 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.

10. SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (191 reviews)
"Best short vacation"
United States
Rommel
$202 nightly
The price is $228
Nov 2 - Nov 3
Total with taxes and fees
SeaSpray Resort
A wooden structure with a thatched roof overlooking a beach.

11. 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 12 - Oct 13
Total with taxes and fees
Casey Key Resort
A beach with clear turquoise water and gentle waves.

12. 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.
$226 nightly
The price is $252
Oct 11 - Oct 12
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
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.
$226 nightly
The price is $252
Oct 11 - Oct 12
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
A beach with clear turquoise water, people swimming and walking along the shore, and a sailboat in the distance.

14. 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.
$229 nightly
The price is $255
Oct 11 - Oct 12
Total with taxes and fees
Sand Dollar Studio, King bed, Pool. Daily Rentals, Walk to Beach.
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

15. 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 11 - Oct 12
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.

16. 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 11 - Oct 12
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A covered patio with a round table and chairs, large windows, and a view of a backyard with a wooden fence and palm trees.

17. 2 miles to #1 Beach Siesta Key

2 miles to #1 Beach Siesta Key
Sarasota
9.8 out of 10, Exceptional, (85 reviews)
"Clean and convenient"
United States
Scott H.
$305 nightly
The price is $340
Oct 18 - Oct 19
Total with taxes and fees
2 miles to #1 Beach Siesta Key
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

18. 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 11 - Oct 12
Total with taxes and fees
Romantic Getaway Beach Club Siesta 202B by RVA
A beach path leading to the sea with grass on either side.

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

Jetties Pointe Cottage #5 - 408 “Casey Key”
Casey Key
9.6 out of 10, Exceptional, (37 reviews)
"Amazing view and beach access, really great stay."
United States
Evan T.
$344 nightly
The price is $383
Oct 13 - Oct 14
Total with taxes and fees
Jetties Pointe Cottage #5 - 408 “Casey Key”
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

20. 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 11 - Oct 12
Total with taxes and fees
Siesta Key 1-Bedroom Condo | Unit 102B at The Beach Club – Steps to the Beach
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

Kompose Boutique Hotel

Kompose Boutique Hotel

10/10 Excellent
"Love staying at the Kompose! Great staff!! Amazing rooms!! Breakfast is 👍👍"
Jacqueline 2-night trip
Posted 1 hour ago
Kompose Boutique Hotel

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.