How much does an Osprey vacation package cost?

Offering great value package deals from $354 on Expedia, you'll be pleasantly surprised at how much a vacation to Osprey costs! Our packages make travel planning easier and your savings go further.

What are the cheapest months to go to Osprey?

You can usually find lower prices and better availability in May, June and September. Check out our cheap Osprey vacation packages and you could get some great off-season discounts.

How many days is enough for Osprey?

You can explore all the top sights in Osprey within a few days, including the popular The Oaks Club . If you want a longer Osprey vacation, check out what sort of activities and day tours are available nearby.

Is it worth booking a vacation package to Osprey?

Osprey offers everything you need for an unforgettable getaway. Get your Osprey vacation off to a flying start by exploring 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 personalize your search by "Property class," "Number of bedrooms," "Traveler 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 traveling on a weekday, when prices are usually lower.

Is it cheaper to book an Osprey vacation as a package?

Expedia vacation 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 customized Osprey vacation by choosing your favorite accommodation type, airline and car class.

When to book a vacation 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?

Pick your travel dates: What you plan to do in Osprey and your preferred season can help you decide when to travel. Figure out your budget: Ensure you have enough money to cover everything from transportation and meals to flights and activities. Your hotel will likely be the biggest expense during your trip to Osprey. Use our trip planning tool to explore Osprey: Research every aspect of your trip to Osprey with this comprehensive planner. Invite your friends and family to collaborate on a group getaway, search for hotels or things to do and make bookings. Set the duration of your trip: Start by making a list of all the activities and attractions you want to experience in Osprey. Then, estimate how long you'll need for each, as well as any travel time. Bundle your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to find an Osprey vacation package that brings all your bookings together. Book activities and experiences in advance: Whether it's a ticket to a big attraction or a day trip in nature, you won't have to worry about missing out on Osprey's best offerings. Find all the fun things to do in Osprey with our dedicated activity guide.

Does Expedia offer Book Now, Pay Later Osprey vacation packages?

Your Osprey trip should be a relaxing escape from your daily routine, not a source of money worries. So to give you a little more flexibility, we've joined up with online lender Affirm to offer our Book Now, Pay Later vacations. Pick one of our vacation packages with payment plans and break down the cost over 3, 6 or 12 months. Plus, there aren't any late payment fees or hidden costs to worry about.

Top Osprey Vacation Packages | Hotel + Flight or Car| Expedia

Your Osprey Vacation

When a getaway to the city is calling, answer it with a Osprey vacation package. The neighborhood of Main Street Merchants, which is great for cafes, markets and shopping, makes a fantastic base for your adventures. Siesta Key Beach, Turtle Beach and Nokomis Beach are just a few of the sights worth exploring during your trip to Osprey. Check out Expedia's extensive range of travel options and book your dream vacation to Osprey now.

The Latest Osprey vacation packages

Price found within the past 48 hours. Click for updated prices.

Lemon Bay Motel

Englewood Central

Save 100% on your flight

$354

per person

Apr 4 - Apr 10

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

8.4/10 Very Good! (39 reviews)

I didn't give a great review initially but outside of the floor being a little dirty and I'm kind of a clean freak it was a very nice room for the price has everything you need really and is greatly centrally located to everything you want to go to and the guy was nice to me in the following days

Reviewed on Jan 12, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

$1,901

per person

Feb 21 - Feb 27

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

9.6/10 Exceptional! (294 reviews)

The room was amazing! Plenty of room, clean, great appliances. Very comfy room

Reviewed on Jan 18, 2026

Seaside at Anna Maria Island Inn

Save 100% on your flight

$2,114

per person

Mar 28 - Apr 1

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9.6/10 Exceptional! (45 reviews)

This location is absolutely beautiful. The room was clean, updated, and right on the beach. The views are amazing. Staff was extremely helpful and made fantastic recommendations. Communication was unexpected, but definitely showed they cared about the guest experience. We would definitely stay here again!

Reviewed on Jan 18, 2026

Hotel Tampa Riverwalk

Downtown Tampa

Save 100% on your flight

$807

per person

Mar 28 - Apr 4

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

7/10 Good! (1,744 reviews)

The hotel was nice. The service in the restaurant was excellent. We loved having close access to the River Walk.

Reviewed on Jan 21, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$2,358

per person

Mar 16 - Mar 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9.2/10 Wonderful! (480 reviews)

Room was clean and staff was friendly

Reviewed on Jan 20, 2026

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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

Osprey Hotel Deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail Osprey FL

Fully refundableReserve now, pay when you stay

$150 nightly

$169 total

Jan 25 - Jan 26

Total with taxes and fees

8.6/10 Excellent! (1,134 reviews)

Yes everything was clean and everybody was courteous

Reviewed on Jan 14, 2026

Kompose Boutique Hotel

965 University Pkwy Sarasota FL

Fully refundableReserve now, pay when you stay

$138 nightly

$156 total

Jan 26 - Jan 27

Total with taxes and fees

9/10 Wonderful! (4,901 reviews)

Loved staying here! It is a really cool hotel. It was clean and comfortable for an amazing price!

Reviewed on Jan 16, 2026

Tropical Beach Resorts

6717 Sara Sea Circle Siesta Key FL

Fully refundableReserve now, pay when you stay

$218 nightly

$246 total

Jan 26 - Jan 27

Total with taxes and fees

9.2/10 Wonderful! (5,237 reviews)

Clean room, comfy bed, adequate kitchen

Reviewed on Jan 17, 2026

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.

Things to do in and around Osprey

Osprey, Florida, is perfect for family vacations and outdoor adventures, offering activities like golfing at local courses and exploring recreational areas. Visitors can enjoy city trips, exciting outdoor excursions, and thrilling backpacking opportunities. Whether you're looking for a relaxing beach day or an adventurous outing, Osprey has something for everyone.

Shopping

In Osprey, you can shop at Sarasota Square, just 3 miles away, offering a vibrant mix of entertainment and family-friendly options. Gulf Gate Mall is another great choice, located 5 miles away. If you're up for a drive, visit Siesta Key Farmers Market, about 7 miles from Osprey.

Recreation

Experience relaxation at Stoneybrook Golf & Country Club, just 2 miles from Osprey, where you can enjoy outdoor sports and scenic views. Indulge in luxury at The Oaks Club, a private country club nearby. For culture and entertainment, visit the Venice Theater, located 7 miles away, perfect for a family night out.

Adventure

Explore the scenic Sarasota BayWalk hiking trail, located 11 miles from Osprey, for stunning views and outdoor adventure. Experience the thrill of the Canopy Walkway and Boylston Nature Trail, 12 miles away, or engage in exciting tennis matches at Payne Park Tennis Center, 10 miles from Osprey.

Nightlife

Osprey offers a laid-back nightlife with cozy bars and restaurants. Enjoy a cocktail at the charming Osprey’s Nest or savor fresh seafood at the nearby Casey Key Fish House. For live music, check out the local venues that often feature talented musicians.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Find the best attractions in and around Osprey

Osprey, Florida, is an ideal destination for beach and outdoor family vacations. Visitors can enjoy popular attractions such as local beaches, urban parks, and jetties, all suited for a fun family experience. With destination resorts nearby, Osprey offers a perfect blend of relaxation and adventure, making it a wonderful spot for travelers seeking both outdoor activities and quality time with loved ones.

Siesta Key Beach: Known for its powdery white sand and stunning sunsets, Siesta Key Beach is a perfect spot to relax and soak up the sun. The beach vibes here are vibrant, making it an ideal destination for sunbathers, swimmers, and beach volleyball enthusiasts alike.
Oscar Scherer State Park: This beautiful state park offers a blend of adventure and scenery, with trails for hiking, biking, and wildlife watching. Experience the great outdoors surrounded by lush landscapes and serene waterways, perfect for a family picnic or a day of exploration.
Point of Rocks: Located on Siesta Key, Point of Rocks features unique limestone formations and vibrant marine life. It's a great spot for snorkeling and taking in picturesque views, offering an unforgettable outdoor experience for nature lovers.

Best time to go to Osprey

The best time to visit Osprey can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Osprey falls in August, when visitor numbers are average and weather is mostly sunny with light rain. The coolest average temperature in Osprey falls in January, visitor numbers are average and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	62.6°F (17.0°C)	Light Rain	Mostly Sunny	Average	Average
February	65.1°F (18.4°C)	No Rain	Mostly Sunny	Average	Slightly High
March	68.0°F (20.0°C)	No Rain	Sunny	Slightly High	Slightly High
April	73.4°F (23.0°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
May	77.7°F (25.4°C)	Light Rain	Mostly Sunny	Average	Average
June	81.7°F (27.6°C)	Light Rain	Mostly Sunny	Average	Average
July	82.9°F (28.3°C)	Light Rain	Mostly Sunny	Average	Average
August	83.3°F (28.5°C)	Light Rain	Mostly Sunny	Average	Slightly Low
September	81.5°F (27.5°C)	Light Rain	Mostly Sunny	Slightly High	Slightly Low
October	77.2°F (25.1°C)	Light Rain	Mostly Sunny	Slightly Low	Average
November	70.7°F (21.5°C)	No Rain	Mostly Sunny	Slightly Low	Slightly Low
December	66.6°F (19.2°C)	No Rain	Mostly Sunny	Slightly Low	Average

Tips to save on your trip to Osprey

Take advantage of package deals on Expedia and combine flights, hotels, or car rentals for a convenient and cost-effective trip to Osprey.
Consider traveling during the off-peak season (typically August to September and November) for more affordable package holidays to Osprey.
Use the Price per traveler filter on Expedia to find a package deal that suits your budget.
Check the VIP Access properties filter to discover outstanding hotels with added member perks at select properties.

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

Language

English

Currency

U.S dollars

Closest Airport

Sarasota-Bradenton Intl. Airport (SRQ)

Population

6,100

Max Temp Winter

70ºF

Max Temp Summer

90ºF