Osprey Village Vacations from $998

Book a Hotel + Flight or Car together to unlock savings

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.
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
Downtown Tampa
Save 100% on your flight
Price was $1,585, price is now $998 per person
$998
per person
Feb 28 - Mar 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
7/10 Good! (1,744 reviews)
Excellent other than did not offer free breakfast.

Reviewed on Dec 5, 2025

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $3,523, price is now $2,001 per person
$2,001
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9.6/10 Exceptional! (294 reviews)
Suite 601 is an exceptional ocean front room with views of sunrise and sunset. The room has top notch appliances and was sparkling clean!

Reviewed on Nov 24, 2025

Legacy Hotel at IMG Academy

Legacy Hotel at IMG Academy

4 out of 5
Save 100% on your flight
Price was $1,772, price is now $1,087 per person
$1,087
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (913 reviews)
HVAC was very loud. I was surprised with a resort fee. This was not disclosed on Expedia Not fair I deserve a refund of $56

Reviewed on Nov 20, 2025

Captiva Beach Resort

Captiva Beach Resort

3 out of 5
South Village
Save 100% on your flight
Price was $1,578, price is now $1,018 per person
$1,018
per person
Mar 1 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,156 reviews)
Clean room, snd friendly staff. Great location

Reviewed on Dec 1, 2025

Manasota Key Resort

Manasota Key Resort

2.5 out of 5
Save 100% on your flight
Price was $1,965, price is now $1,278 per person
$1,278
per person
Jan 9 - Jan 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Sarasota (SRQ)
9.4/10 Exceptional! (252 reviews)
This place is my all time favorite. The staff is very friendly, room was amazing and beach is spectacular!!

Reviewed on Dec 4, 2025

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Discover the most popular places to visit in Osprey Village

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

Oscar Scherer State Park

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 top-notch restaurants.

The Oaks Club

What to do in Osprey Village

Kayak Tour through Mangrove Tunnels

Mangroves, Manatees, and a Hidden Beach: Kayak Tour

$59
per adult
90% of travellers recommend
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
HydroCats

HydroCats - 2 Hour CraigCat Sightseeing Tour

$146
per adult
100% of travellers recommend
HydroCats - 2 Hour CraigCat Sightseeing Tour
Sarasota Guided Mangrove Tunnel Kayak Tour

Sarasota Guided Mangrove Tunnel Kayak Tour

$59
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
See all activities in Osprey Village

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
$87 nightly
The price is $98 total per night from Dec 8 to Dec 9
$98 total
Dec 8 - Dec 9
Total with taxes and fees
9/10 Wonderful! (4,748 reviews)
Beautiful hotel with well kept rooms. Immaculate pool and hot tub area with ping pong, fire, and other activities. Great breakfast, friendly staff. WELL worth your money.

Reviewed on Dec 2, 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
$155 nightly
The price is $175 total per night from Dec 8 to Dec 9
$175 total
Dec 8 - Dec 9
Total with taxes and fees
9.2/10 Wonderful! (5,129 reviews)
Courteous staff. Nice room, short stroll to beach for sunset.

Reviewed on Dec 3, 2025

Tropical Beach Resorts
Carlisle Inn

Carlisle Inn

3.5 out of 5
3727 Bahia Vista Sarasota FL
Fully refundableReserve now, pay when you stay
$170 nightly
The price is $192 total per night from Dec 8 to Dec 9
$192 total
Dec 8 - Dec 9
Total with taxes and fees
9.8/10 Exceptional! (2,131 reviews)
Everything was perfect.

Reviewed on Dec 2, 2025

Carlisle Inn
See all 10,138 properties in Osprey Village
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

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Frequently asked questions

How much does an Osprey Village vacation package cost?
Offering excellent value package deals from $998 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.