Osprey Vacations from $623

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Your Osprey Vacation

When a break in the city is calling, answer it with an Osprey vacation package. The neighborhood of Main Street Merchants, which is good for cafes, markets and shopping, makes an awesome base for your adventures. If your trip to Osprey includes some sightseeing, drop by major attractions such as Siesta Key Beach, Turtle Beach and Nokomis Beach. Don't put off your visit to this destination any longer. Your perfect Osprey vacation is only a few clicks away with Expedia.

The Latest Osprey Vacation Packages

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Jun 19 - Jun 23
Roundtrip flight included
Newark (EWR) to Sarasota (SRQ)
9/10 Wonderful! (358 reviews)
We absolutely loved this place. It was quiet, clean and the staff were all so pleasant. They provide beach chairs and beach towels so no need to worry about bringing those items. We stayed in the Violet cottage and it was perfect for just my husband and I. We cannot wait to visit again

Reviewed on Apr 17, 2024

Siesta Key Island Rentals

Siesta Key Island Rentals

3 out of 5
Save 100% on your flight
per person
May 22 - May 27
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
10/10 Exceptional! (4 reviews)
Very friendly and helpful staffe. Unit was more than what I had expected. Very clean. Newly remodeled. Plenty of room and spacious. Beautiful kitchen/family area

Reviewed on Apr 19, 2024

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Jun 4 - Jun 8
Roundtrip flight included
Chicago (ORD) to Sarasota (SRQ)
9.6/10 Exceptional! (487 reviews)
Very small beach area as large portion was reserved for a chair concession

Reviewed on Apr 11, 2024

Escape Resort & Marina

Escape Resort & Marina

2.5 out of 5
Save 100% on your flight
per person
Jun 20 - Jun 27
Roundtrip flight included
Newark (EWR) to Sarasota (SRQ)
9.8/10 Exceptional! (174 reviews)
We had a great stay, cool spot!

Reviewed on Mar 24, 2024

Captiva Beach Resort

Captiva Beach Resort

2 out of 5
per person
Jun 15 - Jun 19
Roundtrip flight included
Newark (EWR) to Sarasota (SRQ)
9/10 Wonderful! (1,027 reviews)
Great location at the quieter side of Siesta Key beach. Private beach access with lounger hire. Hire costs were maybe a little bit expensive. Free car parking and laundry facilities availability. Regular free trolley bus transport into downtown Siesta Key available.

Reviewed on Apr 13, 2024

Prices and availability subject to change. Additional terms may apply.

Where to stay in Osprey

Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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Sorrento Shores

When in Sorrento Shores, you can plan a visit to Oscar Scherer State Park and Nokomis Beach, some noteworthy sights in the nearby area.

Find hotel + flight trips in Sorrento Shores

Osprey Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sarasota-Bradenton Intl. Airport (SRQ)
Population
6,100
Max Temp Winter
70ºF
Max Temp Summer
90ºF
Top Sights
Siesta Key Beach, Lido Beach and Venice Beach

Osprey Hotel Deals

Casey Key Resorts - Mainland
Casey Key Resorts - Mainland
3 out of 5
1650 South Tamiami Trail, Osprey, FL
Fully refundableReserve now, pay when you stay
The price is $138 per night from Apr 22 to Apr 23
$138
$174 total
includes taxes & fees
Apr 22 - Apr 23
8.4/10 Very Good! (1,000 reviews)
"We stayed here for the 2nd year, as an overnight stop to breakup a long haul to The FL Keys. Customer service at restaurant by the pool was fantastic. Same waitress as last year. She was delightful and attentive! Food is good. The property needs to be dusted more throughly. Always an issue that I ..."

Reviewed on Apr 14, 2024

Casey Key Resorts - Mainland
Kompose Boutique Hotel
Kompose Boutique Hotel
3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is $111 per night from May 13 to May 14
$111
$140 total
includes taxes & fees
May 13 - May 14
8.8/10 Excellent! (3,345 reviews)
Check out this Hidden Gem!
"We were thrilled to have found Kompose Boutique Hotel. The facility is updated, modern, and clean, and has the best and most friendly staff. This was an awesome experience!"

Reviewed on Apr 15, 2024

Kompose Boutique Hotel
Siesta Key Beach Resort and Suites
Siesta Key Beach Resort and Suites
2.5 out of 5
5311 Ocean Blvd, Siesta Key, FL
The price is $207 per night from May 6 to May 7
$207
$283 total
includes taxes & fees
May 6 - May 7
8.6/10 Excellent! (1,000 reviews)
"Perfect experience for family! Will be a returning customer from here on out due to amenities, beach, food, and pool offerings! Thank you!"

Reviewed on Apr 15, 2024

Siesta Key Beach Resort and Suites
See all 10,676 properties in Osprey
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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Kid Friendly Vacations

Kid Friendly Vacations

Frequently asked questions

How much does an Osprey vacation package cost?
Browse and book everything in one place with our Osprey vacation packages, which start from only $623. Select the flights and hotels that suit your travel plans. Then, add on a couple of sightseeing tours for an amazing getaway.
How do I get a cheap travel package to Osprey?
One of the simplest ways to save cash (and time) is to bundle your bookings with Expedia. Hotels, flights, rental cars and activities — we’ve got them all. Select a combination that suits you and watch your savings stack up. Of course, a travel package is never one-size-fits-all. That’s why Expedia offers over 550 airlines and 1,000,000 hotel options across the world, which lets you customize your Osprey getaway.
Where should I stay in Osprey?
With popular attractions like Turtle Beach and Stoneybrook Golf & Country Club in this area, look for a hotel located near them. Oscar Scherer State Park is another sight that pulls the crowds.
What are the top hotels in Osprey?
Travelers going to Osprey often make a booking at Casey Key Resorts - Mainland or Comfy Cozy Place. You’ll find them in Osprey Village. Another great neighborhood is Sorrento Shores. A Tropical 2 Bedroom/2 Bath House W and 15 Mins From Beautiful Siesta Key Beach are popular options in this area.
How far in advance should I book my Osprey vacation?
Reserving your flights early with Expedia means one less thing to have to worry about. Most air carriers advertise tickets up to 12 months in advance. This is usually the cheapest time to book. If circumstances have left you booking late, last-minute deals to Osprey sometimes become available a few weeks before departure.
What does an Expedia Osprey travel package include?
That depends on what sort of getaway you have in the works. Osprey travel deals can include hotels, car rentals and flights. You can mix and match to find the travel package that suits your style and budget. You can also add on activities and experiences after you’ve booked to get even bigger discounts.
What should I know before booking an Osprey travel package?
When you book your hotels, flights and car rentals together, you’ll pick up amazing discounts. Whether you’re planning an island getaway in a villa or would rather stay in a comfortable hotel in the city, Expedia will make it happen for less.
Can I choose my airline with an Osprey Expedia vacation package?
Yes, so take your pick! We offer more than 550 partner airlines worldwide, so you can design your Osprey getaway according to your style and budget.
If I'm not able to travel, can I cancel my Osprey vacation package?
Plans can change without warning, so yes. You may be able to cancel or amend your Osprey vacation package for free within 24 hours of booking. For older bookings, you can still make changes, but your car rental company, hotel or airline may charge a fee. Need more information? Check out our Customer Service Portal. We’re here to help make sure your trip goes off without a hitch.

Discover the most popular places to visit in Osprey

Image for Oscar Scherer State Park

Oscar Scherer State Park

4/5(9 reviews)

Enjoy the beautiful sunsets and explore Oscar Scherer State Park, a lovely green space in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Oscar Scherer State Park
Image for Historic Spanish Point

Historic Spanish Point

You can spend time exploring the galleries in Historic Spanish Point in Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Historic Spanish Point
Image for The Oaks Club

The Oaks Club

Enjoy a round of golf in Osprey at The Oaks Club. Wander the area's beautiful beaches or simply enjoy one of its top-notch restaurants.

The Oaks Club

What to do in Osprey

Image for Mangroves, Manatees, and a Hidden Beach: Kayak Tour

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$50
Per adult
82% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
Image for Sarasota Kayak and Food Tour

Sarasota Kayak and Food Tour

$165
Per adult
Sarasota Kayak and Food Tour
See all activities in Osprey

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.