Osprey Village Vacations from $732
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 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
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.
Casey Key Resorts - Beachfront
$1,077
per person
Dec 1 - Dec 8
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
8.8/10 Excellent! (1,007 reviews)
Very disappointing experience. There was an extremely strong smell of mold and mildew in the hotel. The odor was overwhelming and made our stay very uncomfortable. This is unacceptable for a hotel, especially when guests expect a clean and comfortable environment.
Reviewed on Oct 14, 2026
Landing Palmetto Apartments
$864
per person
Jan 4 - Jan 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (71 reviews)
The apartment had everything we needed. The bathroom vanity was a pedestal sink with no counter space for toiletries.
Reviewed on Oct 12, 2026
Don't see what you're looking for?
See all available trips from Columbus to Osprey Village
View all tripsWhat to do in Osprey Village
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
$65
per adult
86% of travellers recommend
Siesta Key Electric Bike Sunset Tour
$71
per adult
96% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
$59
per adult
94% of travellers recommend
Osprey Village Hotel Deals
Kompose Boutique Hotel
965 University Pkwy Sarasota FL
Fully refundableReserve now, pay when you stay
$60 nightly
$68 total
Oct 28 - Oct 29
Total with taxes and fees
Tropical Beach Resorts
6717 Sara Sea Circle Siesta Key FL
Fully refundableReserve now, pay when you stay
$162 nightly
$183 total
Oct 19 - Oct 20
Total with taxes and fees
9.4/10 Exceptional! (5,980 reviews)
"Location! Location! Perfect for a peaceful getaway. The new pool is gorgeous. The stove and oven needed some instructions how to use took us a bit to figure out. The outside grill was a perfect touch. We will be back. Wonderful time. Great place to go explore point of rocks!"
Reviewed on Oct 17, 2026
Siesta Key Beach Resort and Suites
5311 Ocean Blvd Siesta Key FL
$232 nightly
$262 total
Nov 1 - Nov 2
Total with taxes and fees
9.2/10 Wonderful! (1,184 reviews)
"I had a three night stay at this hotel on Siesta Key. Great location, and I walked every where safely alone. Very friendly staff! My comments on the room. - the mattress needs to be replaced in room 102 - a threshold at the door would be nice to keep any critters from crawling into the room. - the ..."
Reviewed on Oct 15, 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.
Find the Best Osprey Village Vacation Packages
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 |
More vacations you might like
Frequently asked questions
How much does an Osprey Village vacation package cost?
Offering excellent value package deals from $732 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.
