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 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Osprey vacation rentals

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

1. Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$329 nightly
The price is $366
Sep 23 - Sep 24
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida
A grill with a stick over it, a tent, and two chairs in the background.

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

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$329 nightly
The price is $366
Sep 23 - Sep 24
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
A tent with a wooden platform, surrounded by trees and gravel.

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

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$329 nightly
The price is $366
Sep 23 - Sep 24
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
A tented accommodation with a bed, a small table, and a hanging plant.

4. 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)
$329 nightly
The price is $366
Sep 23 - Sep 24
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
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, (5,908 reviews)
"Loved our stay! Definitely recommend"
United States
Alexander
$158 nightly
The price is $179
Sep 27 - Sep 28
Total with taxes and fees
Tropical Beach Resorts
An outdoor patio with a grill, white chairs, and a red umbrella.

6. Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.8 out of 10, Excellent, (2,452 reviews)
"This place was perfect!"
United States
Kat
$116 nightly
The price is $131
Sep 23 - Sep 24
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.

7. Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very good, (385 reviews)
"Great place"
United States
Mario
$184 nightly
The price is $208
Oct 5 - Oct 6
Total with taxes and fees
Tiny House Siesta
A large orange armchair against a white wall with a 'Captiva' sign. There are two potted plants beside the chair.

8. 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
$180 nightly
The price is $201
Sep 23 - Sep 24
Total with taxes and fees
Captiva Beach Resort
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

9. 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
$286 nightly
The price is $323
Sep 30 - Oct 1
Total with taxes and fees
Siesta Key Island Rentals
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, (682 reviews)
"Great stay!!"
United States
Genghis
$205 nightly
The price is $231
Sep 23 - Sep 24
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, (181 reviews)
"Property and room were beautiful!! Right across the street from the beach ⛱️"
United States
Michelle Suzanne
$217 nightly
The price is $245
Sep 28 - Sep 29
Total with taxes and fees
SeaSpray Resort
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

12. 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
Sep 23 - Sep 24
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA
A beach with clear turquoise water and gentle waves.

13. 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.
$238 nightly
The price is $265
Sep 23 - Sep 24
Total with taxes and fees
Siesta Key, Sea Horse Villa, Pool. Daily rentals
A spacious living room with a stone fireplace, comfortable seating, and a view of the outdoors.

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.
$420 nightly
The price is $467
Sep 23 - Sep 24
Total with taxes and fees
Siesta beach....one and only
A beach with clear turquoise water, people swimming and sunbathing, and a sailboat in the distance.

15. 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.
$238 nightly
The price is $265
Sep 23 - Sep 24
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals
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 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.
$305 nightly
The price is $340
Sep 23 - Sep 24
Total with taxes and fees
Siesta Key 1-Bedroom Condo w Private Patio | The Beach Club Vacation Rental
A beach with clear blue water, gentle waves, and a distant sailboat.

17. Siesta Key Village-Suite #1: A block to the Beach!

Siesta Key Village-Suite #1: A block to the Beach!
Siesta Key Village
9.8 out of 10, Exceptional, (47 reviews)
"Great place to stay"
United States
Brad S.
$354 nightly
The price is $383
Sep 23 - Sep 24
Total with taxes and fees
Siesta Key Village-Suite #1: A block to the Beach!
A garden with various plants and a utility pole.

18. Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (132 reviews)
"A beautiful location and super comfortable!"
United States
K B.
$486 nightly
The price is $542
Sep 26 - Sep 27
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage
A beach with rows of umbrellas and beach chairs, a sandy shoreline, and a clear view of the ocean.

19. 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
Sep 23 - Sep 24
Total with taxes and fees
Bright & Beachy–Beach Club Siesta Key 100A by RVA
A beach with tall grasses and a sunset.

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.
$228 nightly
The price is $255
Sep 23 - Sep 24
Total with taxes and fees
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 Hotel Reviews

Carlisle Inn

Carlisle Inn

10/10 Excellent
"My favorite hotel. Clean Lovely .. kind and friendly staff I would never stay anywhere else when in Florida"
Beth 3-night trip
Posted 6 hours ago
Carlisle Inn

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 $131 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 14 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.