Osprey Holidays

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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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

While Sorrento Shores may not have many sights to explore, venturing just a little farther will lead you to top things to see and do like Oscar Scherer State Park and Nokomis Beach.

Find hotels in Sorrento Shores

Top hotels in Osprey

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 S$228 per night from 9 Dec to 10 Dec
S$228
includes taxes & fees
9 Dec - 10 Dec
8.4/10 Very Good! (1,081 reviews)
"Very kind staff"

Reviewed on 14 Nov,2024

Casey Key Resorts - Mainland
Hyatt Regency Sarasota
Hyatt Regency Sarasota
4 out of 5
1000 Blvd Of The Arts, Sarasota, FL
Fully refundableReserve now, pay when you stay
The price is S$303 per night from 1 Dec to 2 Dec
S$303
includes taxes & fees
1 Dec - 2 Dec
8/10 Very Good! (1,002 reviews)
"Very clean and upscale. All staff very courteous and friendly."

Reviewed on 21 Nov,2024

Hyatt Regency Sarasota
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 S$213 per night from 4 Dec to 5 Dec
S$213
includes taxes & fees
4 Dec - 5 Dec
8.8/10 Excellent! (3,599 reviews)
"We stayed 2 nights and were so thrilled to find an affordable option that exceeded our expectations. It was sooo clean. Everywhere we went we saw people cleaning...even in the elevator. The kitchen stafe kept the food areas spotless even at the busiest breakfast hours."

Reviewed on 27 Nov,2024

Kompose Boutique Hotel
See all 10,319 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.

Frequently asked questions

How much does an Osprey holiday package cost?
Browse and book everything in one place with our Osprey holiday packages, which start from only . 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?
Travellers going to Osprey often make a booking at Casey Key Resorts - Mainland or Comfy Cosy Place. You’ll find them in Osprey Village. Another great neighbourhood 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 holiday?
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 holiday 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 holiday package?
Plans can change without warning, so yes. You may be able to cancel or amend your Osprey holiday 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.

What to do in Osprey

Another friendly Sarasota manatee coming over to say hi! It is especially important to protect these great creatures!

Dolphin and Manatee Adventure Tour of Sarasota with Olde Florida History!

S$87
Per adult
Dolphin and Manatee Adventure Tour of Sarasota with Olde Florida History!
Osprey: Guided Dolphin and Manatee SUP or Kayaking Tour

Osprey: Guided Dolphin and Manatee SUP or Kayaking Tour

S$87
Per adult
Osprey: Guided Dolphin and Manatee SUP or Kayaking Tour
Private Luxury Boat Charter

Private Luxury Boat Charter

S$470
Per adult
100% of travellers recommend
Private Luxury Boat Charter
See all activities in Osprey

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.