Osprey Village Vacations from $298

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Your Osprey Village Vacation

When a city getaway is calling, answer it with a Osprey Village vacation package. The neighborhood of Main Street Merchants, which is good for cafes, markets and shopping, makes a wonderful base for your adventures. Every trip to Osprey Village needs a well-crafted itinerary. Fill yours with attractions like Oscar Scherer State Park, The Oaks Club and Historic Spanish Point. Browse Expedia's extensive range of travel options and start planning your ultimate vacation to Osprey Village now.

The Latest Osprey Village vacation packages

Price found within the past 48 hours. Click for updated prices.
DoubleTree by Hilton Tampa Rocky Point Waterfront
The Residences at Siesta Key Beach by Hyatt Vacation Club
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Osprey Village Hotel Deals

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
965 University Pkwy, Sarasota, FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $81 total per night from Oct 16 to Oct 17
$81 total
Oct 16 - Oct 17
Total with taxes and fees
9/10 Wonderful! (4,440 reviews)
"Beautiful hotel especially for the price."

Reviewed on Oct 9, 2025

Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle, Siesta Key, FL
$147 nightly
The price is $166 total per night from Oct 16 to Oct 17
$166 total
Oct 16 - Oct 17
Total with taxes and fees
9.2/10 Wonderful! (5,021 reviews)
"Everything was great. It was the cutest bungalow style studio. It has everything you needed, awesome little kitchenette, little indoor atrium, comfy bed, etc... The bathroom was tiny but clean. I would def stay here again."

Reviewed on Oct 9, 2025

Tropical Beach Resorts
Spark by Hilton Sarasota Siesta Key Gateway

Spark by Hilton Sarasota Siesta Key Gateway

3 out of 5
6600 S Tamiami Trl, Sarasota, FL
Fully refundableReserve now, pay when you stay
$110 nightly
The price is $124 total per night from Oct 16 to Oct 17
$124 total
Oct 16 - Oct 17
Total with taxes and fees
8.2/10 Very Good! (1,758 reviews)
"Rooms were clean and updated. Staff was helpful. Didn’t like that entry is direct from outside and could hear traffic at night."

Reviewed on Oct 14, 2025

Spark by Hilton Sarasota Siesta Key Gateway
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.

Osprey Village Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Sarasota-Bradenton Intl. Airport (SRQ)
Top Sights
Oscar Scherer State Park, Historic Spanish Point and The Oaks Club

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Frequently asked questions

How much does an Osprey Village vacation package cost?
Offering excellent value package deals from $298 on Expedia, you'll be thrilled with how little a vacation to Osprey Village costs! Our packages simplify travel planning and maximize your savings.
What are the cheapest months to go to Osprey Village?
You can usually find lower rates and better availability in May, June and September. Browse our cheap Osprey Village vacation packages and you could score some great off-season deals.
How many days is enough for Osprey Village?
Typically, a handful of days is enough to explore the top attractions during your Osprey Village vacation. But if you want to have time to unwind or take day tours, think about extending your itinerary.
How to find the best Osprey Village package deals?
Use Expedia's handy filters to find some of the best Osprey Village package deals. When you begin your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or search for Osprey Village package deals in the low season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's usually best to lock in your vacation package well in advance.
Is it cheaper to book an Osprey Village vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll usually score a better deal than booking each component individually. And you'll still get the flexibility to create a customized Osprey Village vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Osprey Village?
If you have your Osprey Village travel dates confirmed, book as early as you can to snap up some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Osprey Village vacation packages?
Your Osprey Village trip should be an escape from your busy life, not a source of money worries. So to allow you a bit more flexibility, we've teamed up with online lender Affirm to offer you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total 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.