How much does an Osprey vacation package cost?

Offering great value package deals from $474 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.

Osprey Vacation Packages 2025/2026 from $261

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.

Family Home Tampa

Forest Hills

$474

per person

Jan 28 - Feb 2

found 1 day ago

Roundtrip flight included

Philadelphia (PHL) to Sarasota (SRQ)

7.6/10 Good! (4 reviews)

The Residences at Siesta Key Beach by Hyatt Vacation Club

South Village

Save 100% on your flight

$1,370

per person

Dec 13 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9.6/10 Exceptional! (292 reviews)

Really loved our stay! We had a 3 bedroom apartment with plenty of space and modern amenities. 3 gorgeous walk in showers, enormous bathtub. The complimentary breakfast was very useful with small children. Pool and beach access were great. Complimentary paddle boards and kayaks made it really fun. Location is nice as there is a Breeze shuttle stop at the end of the road but the property itself is in a very quiet location. The sunset was fabulous. We will be back!

Reviewed on Oct 25, 2025

Legacy Hotel at IMG Academy

Save 100% on your flight

$962

per person

Dec 13 - Dec 20

found 1 day ago

Roundtrip flight included

Boston (BOS) to Sarasota (SRQ)

9/10 Wonderful! (900 reviews)

Everyone is exceptionally nice except the front desk woman on the morning of Monday October 6th. Not very friendly. Bad mood.

Reviewed on Oct 6, 2025

Sailport Waterfront Suites

Rocky Point

Save 100% on your flight

$709

per person

Jan 30 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

8.4/10 Very Good! (4,780 reviews)

The room was nice and clean but we had some very loud neighbors celebrating a birthday late Saturday night.

Reviewed on Nov 5, 2025

Hotel Alba, Tapestry Collection by Hilton

Westshore

Save 100% on your flight

$653

per person

Jan 30 - Feb 5

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Sarasota (SRQ)

8.8/10 Excellent! (2,272 reviews)

No puckup at airport. But staff is well trained and customer service is great

Reviewed on Nov 6, 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

Osprey Hotel Deals

Casey Key Resorts - Mainland

1650 South Tamiami Trail, Osprey, FL

Fully refundableReserve now, pay when you stay

$128 nightly

$145 total

Nov 30 - Dec 1

Total with taxes and fees

8.6/10 Excellent! (1,059 reviews)

Clean, comfortable, easy access.

Reviewed on Nov 3, 2025

Kompose Boutique Hotel

965 University Pkwy, Sarasota, FL

Fully refundableReserve now, pay when you stay

$82 nightly

$93 total

Nov 16 - Nov 17

Total with taxes and fees

9/10 Wonderful! (4,584 reviews)

Staff is professional and courteous, the rooms are always clean and the gated lot is always secure. It’s my first choice for staying in Sarasota

Reviewed on Nov 5, 2025

Tropical Beach Resorts

6717 Sara Sea Circle, Siesta Key, FL

Fully refundableReserve now, pay when you stay

$164 nightly

$185 total

Nov 9 - Nov 10

Total with taxes and fees

9.2/10 Wonderful! (5,071 reviews)

We cannot express enough how much we love staying at Tropical Beach Resorts The rooms are fantastic, staff is welcoming, friendly, and helpful.

Reviewed on Nov 2, 2025

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 an ideal destination for beach lovers and families seeking outdoor adventures. Enjoy recreational areas and golf courses while exploring exciting destinations nearby. Whether you're interested in city trips, outdoor excursions, or thrilling backpacking adventures, Osprey offers a variety of activities to create memorable experiences during your vacation.

Shopping

Sarasota Square is a vibrant shopping mall just 3 miles from Osprey, offering entertainment and family-friendly vibes. Gulf Gate Mall, located 5 miles away, features similar offerings. If you're up for a drive, check out the Siesta Key Farmers Market, 7 miles away, for local goods and a city atmosphere.

Recreation

Experience a round of golf at Stoneybrook Golf & Country Club, where you can enjoy the outdoor atmosphere and scenic views. For a touch of luxury, visit The Oaks Club for upscale amenities. Finally, catch a show at Venice Theater for a delightful evening of culture and entertainment.

Adventure

Sarasota BayWalk offers an invigorating hiking trail with stunning views of the bay, located 11 miles from Osprey. For a unique experience, explore the Canopy Walkway and Boylston Nature Trail, a treetop adventure 12 miles away. If you're into sports, visit Payne Park Tennis Center, situated 10 miles from Osprey.

Nightlife

In Osprey, Florida, enjoy a relaxed nightlife at local bars and restaurants along the waterfront. Visit nearby Sarasota for vibrant venues featuring live music, rooftop lounges, and cozy pubs. Explore the charming atmosphere of Siesta Key for beachside bars and late-night entertainment just a short drive away.

*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 a fantastic destination for beach lovers and families seeking outdoor adventures. With its beautiful beaches, urban parks, and picturesque jetties, there's plenty to explore. Visitors can enjoy various attractions that cater to outdoor enthusiasts and families alike. For a more luxurious experience, consider the local destination resorts that enhance your stay in this charming coastal town.

Siesta Key Beach: Located 6 miles from Osprey, Siesta Key Beach is renowned for its powdery white sands and vibrant beach atmosphere. Offering stunning sunsets and crystal-clear waters, it’s perfect for relaxation, swimming, and sunbathing, making it a must-visit for beach lovers.
Oscar Scherer State Park: Situated within Osprey, this national park offers a unique blend of adventure and breathtaking scenery. Explore miles of hiking and biking trails, spot diverse wildlife, and enjoy activities like fishing and kayaking amidst the lush natural surroundings.
Point of Rocks: Just 4 miles from Osprey, Point of Rocks features striking coastal formations and spectacular views. Ideal for snorkeling and tide pooling, this tranquil spot allows visitors to immerse themselves in the beauty of Florida’s natural landscapes.

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