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

Osprey Vacation Rentals

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Our top choices for Osprey vacation rentals

Charming Osprey Home

Charming Osprey Home
Bay Acres
10.0 out of 10, Exceptional, (2 reviews)
"We had a positive experience staying at Linda’s duplex in Osprey. Linda was a lovely host and even furnished us with beach chairs and a cabana . The place was spotless & location was convenient for us as we explored most of the Sarasota, Venice & Naples area. Highly recommended staying at this lovely duplex. "
United States
Diane S.
$395 nightly
The price is $441
Aug 2 - Aug 3
Total with taxes and fees
Charming Osprey Home

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Jul 29 - Jul 30
Total with taxes and fees
Enjoyable Secluded Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Fantastic Tented Cabin with Fire Pit in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Jul 28 - Jul 29
Total with taxes and fees
Fantastic Tented Cabin with Fire Pit in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida

Charming Secluded Tented Cabin in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Jul 28 - Jul 29
Total with taxes and fees
Charming Secluded Tented Cabin in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida
Sarasota
$318 nightly
The price is $354
Jul 28 - Jul 29
Total with taxes and fees
Incredible Tented Cabin with Stunning Forest Views in Sarasota, Florida

Tropical Beach Resorts

Tropical Beach Resorts
3.5 star property
South Village
9.4 out of 10, Exceptional, (5,695 reviews)
"Great location, very close to the beach, very nice and helpful front desk."
United States
Airida
$175 nightly
The price is $198
Aug 11 - Aug 12
Total with taxes and fees
Tropical Beach Resorts

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key
2.5 star property
Sarasota
8.6 out of 10, Excellent, (2,383 reviews)
"Staff was friendly and room was clean"
United States
Maria
$115 nightly
The price is $129
Aug 9 - Aug 10
Total with taxes and fees
Hibiscus Suites - Gateway to Siesta Key

Captiva Beach Resort

Captiva Beach Resort
3.0 star property
South Village
9.0 out of 10, Wonderful, (1,291 reviews)
"Very helpful staff and excellent beach!"
United States
Vania
$173 nightly
The price is $193
Aug 10 - Aug 11
Total with taxes and fees
Captiva Beach Resort

A Beach Retreat

A Beach Retreat
2.5 star property
Casey Key
9.2 out of 10, Wonderful, (655 reviews)
"The beach is right there, very clean and nice place."
United States
Maryna
$205 nightly
The price is $231
Aug 2 - Aug 3
Total with taxes and fees
A Beach Retreat

SeaSpray Resort

SeaSpray Resort
4.0 star property
Siesta Key
9.6 out of 10, Exceptional, (155 reviews)
"We love the hotel the cleaners the facility was amazing"
United States
yisel
$269 nightly
The price is $304
Aug 9 - Aug 10
Total with taxes and fees
SeaSpray Resort

Tiny House Siesta

Tiny House Siesta
2.0 star property
Sarasota
8.4 out of 10, Very Good, (382 reviews)
"Great place"
United States
Mario
$133 nightly
The price is $150
Aug 3 - Aug 4
Total with taxes and fees
Tiny House Siesta

The Ringling Beach House

The Ringling Beach House
3.5 star property
Siesta Key
9.0 out of 10, Wonderful, (374 reviews)
"In resume the property is amazing"
United States
Lazaro
$360 nightly
The price is $407
Jul 31 - Aug 1
Total with taxes and fees
The Ringling Beach House

Siesta Key Island Rentals

Siesta Key Island Rentals
3.0 star property
Siesta Key
9.6 out of 10, Exceptional, (73 reviews)
"Great location, very clean and spacious."
United States
Jason
$337 nightly
The price is $381
Jul 28 - Jul 29
Total with taxes and fees
Siesta Key Island Rentals

Casey Key Beachfront Escape: Charming 1BR Cottage

Casey Key Beachfront Escape: Charming 1BR Cottage
Casey Key
9.4 out of 10, Exceptional, (128 reviews)
"We loved the cottage on the beach. The view was wonderful. Very peaceful location. The cottage was clean and had everything we needed. Highly recommend!"
United States
Virginia W.
$488 nightly
The price is $544
Aug 14 - Aug 15
Total with taxes and fees
Casey Key Beachfront Escape: Charming 1BR Cottage

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

2BR Beach Style w Pool Beach Club Siesta 204C RVA
South Village
8.8 out of 10, Excellent, (80 reviews)
"Beautiful place"
United States
Chad
$419 nightly
The price is $467
Jul 28 - Jul 29
Total with taxes and fees
2BR Beach Style w Pool Beach Club Siesta 204C RVA

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool
Siesta Key
9.4 out of 10, Exceptional, (99 reviews)
"Great location"
United States
Daphane
$376 nightly
The price is $419
Aug 14 - Aug 15
Total with taxes and fees
Walk to the Beach and More from this Fully Renovated Unit W/ Heated Pool

The Beach Club at Siesta Key #106D Resort by RVA

The Beach Club at Siesta Key #106D Resort by RVA
South Village
9.4 out of 10, Exceptional, (62 reviews)
"Great!"
United States
Douglas
$428 nightly
The price is $478
Jul 28 - Jul 29
Total with taxes and fees
The Beach Club at Siesta Key #106D Resort by RVA

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, (104 reviews)
"Awesome location and the staff was great!"
United States
John F.
$295 nightly
The price is $329
Aug 2 - Aug 3
Total with taxes and fees
Couple’s Escape-Beach Club at Siesta Key 106C by RVA

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)
"Everything was very clean, great location, perfect for a couple and enjoyed the pool area too"
United States
Dirk T
$299 nightly
The price is $333
Jul 31 - Aug 1
Total with taxes and fees
Siesta Key, Walk to Beach. POOL VIEW. King Bed. Daily Rentals

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!

House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
South Village
9.2 out of 10, Wonderful, (141 reviews)
"Accommodations were perfect for our family of 6. Extremely convenient to have private beach access along with chairs and ability to get umbrellas for shade."
United States
James N.
$777 nightly
The price is $865
Aug 6 - Aug 7
Total with taxes and fees
House of The Sun on Crescent Beach: Beachfront Bliss w/ Heated Pool, Tennis & Free VIP Perks Daily!
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

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 $129 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 lively bars in this destination. While you're in the area, you can also enjoy the top-notch restaurants and shops.

What are some of the best vacation rentals in Osprey?

Siesta Key Island Rentals: This vacation home rental near Osprey comes with free WiFi so you can feel at home during your trip. This vacation rental also comes with free parking to give you added peace of mind.

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?

Family-friendly attractions include Jim Neville Marine Preserve and Nancy's Consignments, whereas Turtle Beach and Nokomis Beach are a couple of great spots to enjoy the outdoors. 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.