Osprey Village Vacations from $298
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.
DoubleTree by Hilton Tampa Rocky Point Waterfront
Rocky Point
Save 100% on your flight
Price was $475, price is now $298 per person
$298
per person
Nov 16 - Nov 20
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
8.2/10 Very Good! (1,003 reviews)
Our initial room was dirty. Dirty hand prints on walls and lamp shades. Broken door handle and also dirty wall in the bathroom. The carpet in the room had a huge rip in it. I was given another room. Staffing shortage was an issue. The bar and outdoor areas were not kept up. Empty plastic cups and trash were all over the place.
Reviewed on Oct 13, 2025
The Residences at Siesta Key Beach by Hyatt Vacation Club
South Village
Save 100% on your flight
Price was $1,033, price is now $594 per person
$594
per person
Dec 15 - Dec 18
found 14 hours ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
9.6/10 Exceptional! (290 reviews)
We celebrated my daughter’s 30th birthday and it was perfect. I can’t wait to stay again. The beach was truly amazing. This place has everything you need.
Reviewed on Sep 15, 2025
Captiva Beach Resort
South Village
Save 100% on your flight
Price was $1,235, price is now $766 per person
$766
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Sarasota (SRQ)
9/10 Wonderful! (1,132 reviews)
Loved my stay here, it has been renovated and the room was perfect with a big shower, comfy bed and a nice kitchen. The beach is right next door and restaurants, market, shopping in walking distance. The trolley to downtown is across the street and free, just give the driver a tip :) The property has a great outdoor courtyard area for lounging. I enjoyed staying at this quaint 1950's style property that is part of other smaller original properties versus the big high rises that have take over the area. I plan to stay here next time I visit Siesta Key!
Reviewed on Oct 13, 2025
Venice Beach Villas
Save 100% on your flight
Price was $1,104, price is now $704 per person
$704
per person
Dec 21 - Dec 27
found 1 day ago
Roundtrip flight included
New York (NYC) to Sarasota (SRQ)
9.4/10 Exceptional! (440 reviews)
Everyone there takes their property seriously. Perfectly maintained and friendly people
Reviewed on Oct 8, 2025
Don't see what you're looking for?
See all available trips from Columbus to Osprey Village
View all tripsDiscover the most popular places to visit in Osprey Village
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.
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.
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.
What to do in Osprey Village
Mangroves, Manatees, and a Hidden Beach: Kayak Tour
$55
per adult
88% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
$65
per adult
74% of travellers recommend
Siesta Key, FL - Clear Kayak LED Night Glass Bottom Tour
$65
per adult
Osprey Village Hotel Deals
Kompose Boutique Hotel
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
Tropical Beach Resorts
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
Spark by Hilton Sarasota Siesta Key Gateway
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
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 |
More vacations you might like
Frequently asked questions
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.