Winston Park Vacations from $344

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Your Winston Park Vacation

Our Winston Park vacation packages are a speedy and practical way to arrange and book your next retreat. Get to know the essence of this unique neighborhood without the fuss of planning everything yourself. Not sure what to do during your trip to Winston Park? Nearby attractions such as Weedon Island Preserve, The Skyway Shopping Center and Sawgrass Lake Park are great places to start. Whatever your travel plans or the size of your budget, booking your dream Winston Park vacation is simple with Expedia.

The Latest Winston Park Vacation Packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $554, price is now $344 per person
$344
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,944, price is now $1,502 per person
$1,502
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Excellent room and facility . Clean and exactly like online pictures .

Reviewed on Oct 9, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $3,143, price is now $1,641 per person
$1,641
per person
Dec 30 - Jan 4
found 24 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Clean, quite, nice staff

Reviewed on Oct 6, 2025

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $2,313, price is now $1,269 per person
$1,269
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,068 reviews)
Have stayed here a couple times now and would definitely go back. Love the vibes. Only thing that was a bummer is that my daughter and I love using the complimentary bikes to ride around town. However, the bikes are in pretty rough shape. If doable, I would consider maybe replacing the bikes.

Reviewed on Oct 7, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,175, price is now $739 per person
$739
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,661 reviews)
We enjoyed the property and closeness to the beach. Restaurants were walkable. Pool bar food could be upgraded but found the remainder of the dinning options suitable. We had a great time and would recommend.

Reviewed on Oct 7, 2025

Where to stay in Winston Park

Find the best Winston Park areas and neighborhoods for the activities you enjoy most. Learn more about Winston Park
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Winston Park Hotel Deals

Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $242 total per night from Oct 16 to Oct 17
$242 total
Oct 16 - Oct 17
Total with taxes and fees
8/10 Very Good! (2,226 reviews)
"All Great!"

Reviewed on Oct 5, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr, Tampa, FL
Fully refundableReserve now, pay when you stay
$147 nightly
The price is $169 total per night from Oct 13 to Oct 14
$169 total
Oct 13 - Oct 14
Total with taxes and fees
6.8/10 (1,680 reviews)
"Great stay, dj on the pool very nice, clean rooms nice staff"

Reviewed on Oct 5, 2025

Hotel Tampa Riverwalk
Hilton St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
$109 nightly
The price is $123 total per night from Oct 26 to Oct 27
$123 total
Oct 26 - Oct 27
Total with taxes and fees
7.6/10 Good! (1,010 reviews)
"The valet parking at this hotel is ridiculously expensive. Park at Camden Pier carpark directly behind the hotel for a third of the price. Very handy for the Rowdies ground which is opposite. Loved our stay here."

Reviewed on Oct 6, 2025

Hilton St. Petersburg Bayfront
See all 16,429 properties in Winston Park
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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Winston Park

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$32
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.