Osprey Vacations from $300

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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.
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
Westshore
Save 100% on your flight
per person
Aug 6 - Aug 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
8.8/10 Excellent! (1,945 reviews)
Everything was great!!!

Reviewed on Jul 5, 2025

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
per person
Sep 8 - Sep 15
found 1 day ago
Roundtrip flight included
New York (JFK) to Sarasota (SRQ)
9.2/10 Wonderful! (445 reviews)
My family and I had a wondeful stay here, beds were comfortable, ac worked well, friendly and attentive staff, etc. Definitely recommend staying here and will be back soon.

Reviewed on Jun 20, 2025

Escape Resort & Marina

Escape Resort & Marina

2.5 out of 5
Save 100% on your flight
per person
Sep 11 - Sep 16
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
9.8/10 Exceptional! (206 reviews)
Felt right at home! We cannot wait to go back. Pool was great, cart with chairs and umbrella made beach day so easy. We didn’t kayak or bike, but it’s on the list for next time.

Reviewed on Jun 7, 2025

Twin Palms at Siesta

Twin Palms at Siesta

3 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (544 reviews)
Property was very nice, room was beautifully decorated and very clean and comfortable. Nice kitchenette. The pool and pool area very nice. The location is great. Close to the beach and some restaurants and bars. Each room was provided a wagon, cooler, chairs and umbrella to use for the beach which was so nice. I would definitely stay there again!

Reviewed on Jun 29, 2025

Barsala at Champions Walk

Barsala at Champions Walk

4 out of 5
Save 100% on your flight
per person
Aug 15 - Aug 20
found 22 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
7.2/10 Good! (40 reviews)
Absolutely beautiful location has everything you need n makes you feel like home

Reviewed on Jun 24, 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

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 hotels in Sorrento Shores

Discover the most popular places to visit in Osprey

Great national park to take your RV and lots of hiking and biking trails.

Oscar Scherer State Park

4/5(9 reviews)

You can take time to visit Oscar Scherer State Park during your travels to Osprey. Attend a sporting event or simply enjoy the lively bars while you're in the area.

Oscar Scherer State Park
#church

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

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 lively bars.

The Oaks Club

What to do in Osprey

Private Luxury Boat Charter

Private Luxury Boat Charter

$375
per traveler
100% of travellers recommend
Private Luxury Boat Charter
Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$55
per adult
88% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
See all activities in Osprey

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
$124 nightly
The price is $140 total per night from Jul 6 to Jul 7
$140 total
Jul 6 - Jul 7
Total includes taxes and fees
8.4/10 Very Good! (1,053 reviews)
Great!
"Clean ans affordable"

Reviewed on Jun 27, 2025

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
$80 nightly
The price is $91 total per night from Jul 9 to Jul 10
$91 total
Jul 9 - Jul 10
Total includes taxes and fees
9/10 Wonderful! (4,070 reviews)
"It’s quite close to Airport but I feel the hotel should keep an Airport Drop shuttle as it’s not easy walk with Luggage and secondly a welcome bottle of water will be nice to offer to all guest. I arrived on a very hot afternoon-evening and the reception didn’t offer any welcome drink or bottle of ..."

Reviewed on Jul 5, 2025

Kompose Boutique Hotel
Tropical Beach Resorts
Tropical Beach Resorts
3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
Fully refundableReserve now, pay when you stay
$181 nightly
The price is $204 total per night from Jul 6 to Jul 7
$204 total
Jul 6 - Jul 7
Total includes taxes and fees
9.2/10 Wonderful! (4,739 reviews)
"Property is located on the beach side of the roadway so we didn't have to walk only about 100 ft to the beach! Rentals on the beach for chairs and umbrellas."

Reviewed on Jul 2, 2025

Tropical Beach Resorts
See all 10,455 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.

Find the Best Osprey Vacation Packages

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

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Frequently asked questions

How much does an Osprey vacation package cost?
Offering great value package deals from $300 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?

  1. Pick your travel dates: What you plan to do in Osprey and your preferred season can help you decide when to travel.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.