Willow Vacation Packages

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Your Willow Vacation

Prepare to experience Willow in your own style with a custom Willow vacation package! Discovering the best parts of this fascinating city is simpler with a base in a neighborhood such as Caloosa, which is great for golfing, among lots of other things. Make sure to spend time sightseeing during your trip to Willow. Florida Railroad Museum and South Fork State Park are some top places to visit. Stop daydreaming and start doing. Explore the broad range of options on Expedia today and put your Willow vacation plans in motion!

Top Willow Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Price was CA $1,426, price is now CA $830 per person
CA $830
per person
Aug 20 - Aug 27
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (80 reviews)
I had a wonderful stay! The room was clean, and exactly what I needed. I have issues sleeping and the mattress was a bit to soft for me. Outside of that, the location was quite and close to all the fun I had. I would stay again.

Reviewed on Jul 12, 2026

Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Price was CA $2,820, price is now CA $1,663 per person
CA $1,663
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
9.2/10 Wonderful! (543 reviews)
Staff and property was 10/10!!

Reviewed on Jul 13, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $2,554, price is now CA $1,672 per person
CA $1,672
per person
Aug 26 - Sep 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!

Reviewed on Jul 8, 2026

The Sarasota Modern, a Tribute Portfolio Hotel

The Sarasota Modern, a Tribute Portfolio Hotel

4 out of 5
Central Sarasota
Price was CA $1,217, price is now CA $857 per person
CA $857
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.2/10 Very good! (559 reviews)
Super helpful staff

Reviewed on Jun 23, 2026

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,271, price is now CA $912 per person
CA $912
per person
Aug 22 - Aug 29
found 1 day ago
Roundtrip flight included
Detroit (DTW) to Tampa (TPA)
8.6/10 Excellent! (2,353 reviews)
This is truly a hidden gem in siesta key! This hotel had all you could ever need. The kitchen had plenty to make home made meals, fridge was full size, plenty of utensils and pot/pans. Living room and dining room were plenty for a family of 3. The bedroom was spacious and beds were very comfortable. Full size bathroom and vanity with chair. The pool was amazing, the hotel offers plenty of towel, toys and have a grill available. The office offers fresh coffee 24 hours a day. The front staff was super friendly and gave you all the information on surrounding area activities. They have plenty of parking and offer frog hop, which takes you anywhere you want to go (on siesta key).

Reviewed on Jul 12, 2026

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Willow Hotel Deals

EVEN Hotel Sarasota-Lakewood Ranch by IHG

EVEN Hotel Sarasota-Lakewood Ranch by IHG

3.5 out of 5
6231 Lake Osprey Dr Sarasota FL
Fully refundable
The price is CA $147 per night from Jul 19 to Jul 20
CA $147
CA $166 total
Jul 19 - Jul 20
includes taxes & fees
8.4/10 Very good! (1,026 reviews)
"Ice water in the lobby & every room has exercise equipment. Best hotel for staying in shape."

Reviewed on Jul 12, 2026

EVEN Hotel Sarasota-Lakewood Ranch by IHG
Extended Stay America Premier Suites - Bradenton

Extended Stay America Premier Suites - Bradenton

2.5 out of 5
4550 53rd Ave E Bradenton FL
Fully refundableReserve now, pay when you stay
The price is CA $103 per night from Jul 19 to Jul 20
CA $103
CA $117 total
Jul 19 - Jul 20
includes taxes & fees
8.8/10 Excellent! (691 reviews)
"Clean room, cool air conditioning. All what you need"

Reviewed on Jul 13, 2026

Extended Stay America Premier Suites - Bradenton
Courtyard by Marriott Bradenton Sarasota Riverfront

Courtyard by Marriott Bradenton Sarasota Riverfront

3 out of 5
100 Riverfront Drive W Bradenton FL
Fully refundableReserve now, pay when you stay
The price is CA $155 per night from Jul 19 to Jul 20
CA $155
CA $175 total
Jul 19 - Jul 20
includes taxes & fees
8.6/10 Excellent! (1,015 reviews)
"Disappointing Courtyard but the place was okay"

Reviewed on Jul 13, 2026

Courtyard by Marriott Bradenton Sarasota Riverfront
See all 2,035 properties in Willow
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
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Stay near popular Willow attractions

Florida Railroad Museum Willow Yard

You can spend time browsing the exhibits at Florida Railroad Museum Willow Yard in Willow.
See properties

What to do in Willow

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour

CA $85
per adult
90% of travellers recommend
Anna Maria Island and Bradenton: Sunset Kayak Dolphin Tour
Picture 4 for Activity Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

Bradenton: Anna Maria Island Guided Kayaking Manatee Tour

CA $78
per adult
100% of travellers recommend
Bradenton: Anna Maria Island Guided Kayaking Manatee Tour
Anna Maria Island: The Island Kayak Tour

Anna Maria Island: The Island Kayak Tour

CA $92
per adult
100% of travellers recommend
Anna Maria Island: The Island Kayak Tour
See all activities in Willow

Frequently asked questions

How much does a Willow vacation package cost?
You'll find cheap prices from CA $830 on Expedia for your Willow break. However, factors like the length of stay, hotel choice and season will influence how much your vacation to Willow costs.
What are the cheapest months to go to Willow?
If you're looking to book a cheap Willow vacation package, consider visiting in January, February and September. You'll typically find better rates on flights and hotels during these quieter months — ideal for a budget-friendly break.
How many days is enough for Willow?
With a well-planned itinerary, you can easily visit the most popular Willow sights in a few days. But if you'd like to venture off the beaten track or take day trips, think about booking your Willow vacation for longer.
How to find the best Willow package deals?
Use Expedia's handy filters to find some fabulous Willow package deals. When you start your search, simply set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your break for midweek, or browse for Willow package deals in the low season. Play around with your travel dates and you may land even better discounts. As a rule of thumb, it's typically best to lock in your vacation package as early as possible.
Is it cheaper to book a Willow vacation as a package?
You can enjoy significant savings on your Willow retreat by booking a customized vacation package. Click on the "Package" heading, then enter your travel dates and destination to browse the best flight and hotel prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may score a better deal.
When to book a vacation package to Willow?
If you're considering an impromptu Willow trip, check out our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find sensational deals on your hotels and flights by booking well in advance.
How to plan a trip to Willow?

  1. Choose the ideal time to travel: Your schedule, preferred season and the type of weather you enjoy can all impact your decision on when to travel to Willow.
  2. Calculate your budget: Ensure you have enough money to cover everything from transportation and dining out to activities and airfares. Your accommodations will likely be the biggest expense during your trip to Willow.
  3. Decide how many days away: Start by compiling a list of the activities and attractions you want to get to in Willow. Then, estimate how long you'll need at each, along with any travel time.
  4. Bundle your bookings: With your travel dates in place, you can combine your car rental, flights, hotels and more into a customized Willow vacation package.

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