Osprey Village Vacation Packages

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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.

Top Osprey Village Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Casey Key Resorts - Mainland

Casey Key Resorts - Mainland

4 out of 5
Price was CA $1,094, price is now CA $975 per person
CA $975
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Sarasota (SRQ)
8.6/10 Excellent! (1,247 reviews)
I received excellent customer service at Casey Key Resorts. They truly care about their guests. When I checked in, I was greeted by Nan. She was very accommodating to my room request. The next day, I had another request and spoke with Nicole at the front desk. She provided me with exceptional customer service to ensure that I had a very comfortable and peaceful staycation. Thank you!😊💜

Reviewed on Oct 27, 2026

Landing Palmetto Apartments

Landing Palmetto Apartments

4.5 out of 5
Price was CA $1,345, price is now CA $1,065 per person
CA $1,065
per person
Nov 28 - Dec 5
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9/10 Wonderful! (73 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

Escape Coastal Resort on Casey Key

Escape Coastal Resort on Casey Key

2.5 out of 5
Price was CA $2,005, price is now CA $1,702 per person
CA $1,702
per person
Dec 30 - Jan 6
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.8/10 Exceptional! (316 reviews)
The manager, Mark was very personable and knowledgeable about the area. We stayed in #18 Oceanfront ground floor for our 3rd anniversary. Everyone & everything was just perfect. This is a real gem. Recently remodeled...was absolutely stunning.

Reviewed on Oct 27, 2026

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

Holiday Inn Express & Suites Nokomis Sarasota South by IHG

2.5 out of 5
Price was CA $1,208, price is now CA $1,033 per person
CA $1,033
per person
Dec 30 - Jan 6
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Sarasota (SRQ)
9.4/10 Exceptional! (616 reviews)

Casey Key Resorts - Beachfront

Casey Key Resorts - Beachfront

3 out of 5
Price was CA $1,675, price is now CA $1,439 per person
CA $1,439
per person
Dec 2 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Ottawa (YOW) to Sarasota (SRQ)
8.8/10 Excellent! (1,006 reviews)
Perfect laid back location on the gulf! Room was clean & beach chairs & umbrellas were an added bonus!

Reviewed on Oct 26, 2026

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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
The price is CA $104 per night from Nov 25 to Nov 26
CA $104
CA $147 total
Nov 25 - Nov 26
includes taxes & fees
Kompose Boutique Hotel
Tropical Beach Resorts

Tropical Beach Resorts

3.5 out of 5
6717 Sara Sea Circle Siesta Key FL
The price is CA $208 per night from Nov 2 to Nov 3
CA $208
CA $271 total
Nov 2 - Nov 3
includes taxes & fees
9.4/10 Exceptional! (6,020 reviews)
"Nice, clean, and just renovated room. Nice front desk host. Just on beach"

Reviewed on Oct 28, 2026

Tropical Beach Resorts
Siesta Key Beach Resort and Suites

Siesta Key Beach Resort and Suites

2.5 out of 5
5311 Ocean Blvd Siesta Key FL
The price is CA $205 per night from Nov 17 to Nov 18
CA $205
CA $309 total
Nov 17 - Nov 18
includes taxes & fees
Siesta Key Beach Resort and Suites
See all 10,823 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
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What to do in Osprey Village

Mangroves, Manatees & a Hidden Beach Kayak Tour

Mangrove Tunnel & Manatee Kayak Eco-Tour

CA $83
per adult
96% of travellers recommend
Mangrove Tunnel & Manatee Kayak Eco-Tour
Sarasota Guided Mangrove Tunnel Kayak Tour

Sarasota Guided Mangrove Tunnel Kayak Tour

CA $83
per adult
96% of travellers recommend
Sarasota Guided Mangrove Tunnel Kayak Tour
Sarasota - Clear Kayak LED Night Glass Bottom Tour

Sarasota - Clear Kayak LED Night Glass Bottom Tour

CA $92
per adult
78% of travellers recommend
Sarasota - Clear Kayak LED Night Glass Bottom Tour
See all activities in Osprey Village

Frequently asked questions

How much does an Osprey Village vacation package cost?
You can grab a vacation package to this top destination from CA $975 on Expedia. However, how much your vacation to Osprey Village costs will depend on factors like your hotel choice, season and length of stay.
What are the cheapest months to go to Osprey Village?
If you'd like to snag a cheap Osprey Village vacation package, consider travelling in January, February and August. You'll usually find lower rates on accommodations and flights during these months — ideal for budget-conscious travellers.
How many days is enough for Osprey Village?
You can easily visit all the main attractions in Osprey Village within a few days, including the must-see Historic Spanish Point. If you're after a longer Osprey Village vacation, check out which kind of activities and day trips are available close by.
How to find the best Osprey Village package deals?
Finding a cheap Osprey Village package deal is a breeze with Expedia. After you've entered your destination and trip dates under our "Packages" tab, set your budget range, add a few filters and see what's available. You can fine-tune your search by "Popular locations," "Property type," "Guest rating" and more. Order the results by "Price: low to high" to view the most pocket-friendly Osprey Village package deals. Want a simple trick to score even more savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are generally lower.
Is it cheaper to book an Osprey Village vacation as a package?
An Expedia vacation package could score you significant savings when compared to arranging flights and hotels individually. Better still, you can customize your Osprey Village escape to fit your exact style. Pick your preferred flight time, select the hotel type and add a car rental. Check out our great deals to see how much you can save.
When to book a vacation package to Osprey Village?
If you have your Osprey Village vacation dates finalized, book as early as you can to grab some fantastic deals. With Expedia, you can often reserve some flights up to one year ahead of time. Prefer spontaneous trips? Our last-minute deals are ideal for jetting off on a whim.
How to plan a trip to Osprey Village?

  1. Choose the perfect time to travel: Your schedule, favourite season and the type of weather you like can all impact your decision on when to go to Osprey Village.
  2. Plan your budget wisely: As well as the cost of your accommodations, you should factor in other expenses too. These include flights, transportation and food. Also, put aside some extra funds for unexpected expenses that may arise during your trip to Osprey Village.
  3. Decide your trip length: Think about how much time you'd like to spend discovering Osprey Village. Plan your itinerary so you can get to all the attractions and activities you're interested in at a comfortable pace.
  4. Bundle your bookings: With your travel dates in order, you can combine your hotels, flights, car rental and more into a customized Osprey Village vacation package.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.