Osprey Holidays
- Plan, book, travel with confidence
- Better togetherSave up to S$1,300 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, book, and manage your trip all in one place
Where to stay in Osprey
Find the best Osprey areas and neighborhoods for the activities you enjoy most. Learn more about Osprey
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.
Rivendell
Though Rivendell may not have many top sights, you can venture to the surrounding area to see attractions like Oscar Scherer State Park and Turtle Beach.
Bay Acres
When in Bay Acres, you can plan a visit to Historic Spanish Point and Oscar Scherer State Park, some noteworthy sights in the nearby area.
Top hotels in Osprey
Casey Key Resorts - Mainland
1650 South Tamiami Trail Osprey FL
Fully refundableReserve now, pay when you stay
S$137
7 Oct - 8 Oct
includes taxes & fees
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
S$83
5 Oct - 6 Oct
includes taxes & fees
9.2/10 Wonderful! (6,017 reviews)
"I stay here all the time because it’s a terrific value."
Reviewed on 21 Sept, 2026
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
S$228
27 Sept - 28 Sept
includes taxes & fees
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.
Stay near popular Osprey attractions
Photo by Frank Methling
Oscar Scherer State Park
8.8/10 (83 reviews)
A sanctuary for endangered Florida scrub-jays, Oscar Scherer State Park offers trails through diverse ecosystems. Paddle South Creek or swim in Lake Osprey after spotting wildlife in the scrubby flatwoods.
Photo by Jessica M Dobbins
Historic Spanish Point
9.0/10 (42 reviews)
This 30-acre outdoor museum showcases Florida history through shell middens and pioneer buildings. Stroll through Bertha Palmer's bayfront gardens while exploring archaeological treasures spanning millennia.
What to do in Osprey
Lido Key: Self-Guided Paddleboard Rental
S$55
per adult
100% of travellers recommend
Siesta Key Electric Bike Sunset Tour
S$91
per adult
96% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
S$185
per adult
100% of travellers recommend
Frequently asked questions
How much does an Osprey holiday package cost?
Offering great value package deals on Expedia, you'll be pleasantly surprised at how much a holiday to Osprey costs! Our packages make travel planning easier and your savings go further.
What are the cheapest months to go to Osprey?
August, September and November are great times to look for cheap Osprey holiday packages. Travelling in less busy periods means you can usually find lower prices on hotels and flights.
How many days is enough for Osprey?
Dedicate at least 3 days for your Osprey holiday to really immerse yourself in everything that makes this place special. Stroll around popular areas, including Laurel and Casey Key. Then make a beeline for major sights such as Oscar Scherer State Park and The Oaks Club. With a clever itinerary, you'll be kept busy with room for some relaxation too. Want to venture beyond Osprey? Consider squeezing in a day trip or two.
Is it worth booking a holiday package to Osprey?
Osprey has everything you need for an amazing trip. Get your Osprey holiday off to a flying start by checking out major attractions like Oscar Scherer State Park.
How to find the best Osprey package deals?
Bagging a cheap Osprey package deal is easy with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can personalise your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Order the results by "Price: low to high" to view the most wallet-friendly Osprey package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider travelling on a weekday, when prices are usually lower.
Is it cheaper to book an Osprey holiday as a package?
Expedia holiday packages are designed to give you more bang for your buck. Bundle your car rental, hotel and flight into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component individually. And you'll still have the flexibility to create a customised Osprey holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday package to Osprey?
Score incredible bargains by reserving your flights ahead of time with Expedia. If spontaneity is more your style, snap up one of our last-minute deals for an impromptu Osprey getaway.
How to plan a trip to Osprey?
- Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all influence your decision on when to visit Osprey.
- Budget wisely: On top of the cost of your hotel, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside a little extra for unexpected expenses that may crop up during your trip to Osprey.
- Decide how long to go away for: Now that you're more familiar with Osprey, you can work out the ideal length of your break. Put together a rough itinerary and allocate enough time for all the things you want to do.
- Bundle your hotel and flights: Awesome destination, check. Length of stay, check. Now all that's left is to choose an Osprey holiday package that brings all your bookings together.
* 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.
