Winston Park Vacations from $297

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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.
New Hotel Collection Harbourside

New Hotel Collection Harbourside

3 out of 5
Save 100% on your flight
Price was $514, price is now $297 per person
$297
per person
Oct 2 - Oct 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.8/10 Good! (507 reviews)
Great service and very nice place to stay!! Definitely will be coming back.

Reviewed on Aug 6, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $788, price is now $427 per person
$427
per person
Oct 7 - Oct 14
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
8.6/10 Excellent! (59 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $578, price is now $326 per person
$326
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,000 reviews)
Better than the Westin.

Reviewed on Aug 26, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,023, price is now $605 per person
$605
per person
Nov 2 - Nov 6
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (598 reviews)
I love it, all staff super nice Beautiful place, clean, awesome beach Thanks

Reviewed on Aug 24, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,787, price is now $1,061 per person
$1,061
per person
Oct 20 - Oct 27
found 2 days ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,549 reviews)
The staff were amazing and very friendly. The breakfast buffet was good and the gym was well equipped. Plenty of places within walking distance to eat and shop. We will definitely be back!

Reviewed on Aug 27, 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

RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
$177 nightly
The price is $200 total per night from Sep 7 to Sep 8
$200 total
Sep 7 - Sep 8
Total with taxes and fees
8.2/10 Very Good! (1,378 reviews)
"Go every year. Always a joy to be there."

Reviewed on Aug 23, 2025

RumFish Beach at TradeWinds
Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and fees
8.4/10 Very Good! (1,012 reviews)
"Nice rooms"

Reviewed on Aug 25, 2025

Hilton Tampa Airport Westshore
Grand Hyatt Tampa Bay

Grand Hyatt Tampa Bay

4 out of 5
2900 Bayport Drive, Tampa, FL
Fully refundableReserve now, pay when you stay
$200 nightly
The price is $227 total per night from Aug 29 to Aug 30
$227 total
Aug 29 - Aug 30
Total with taxes and fees
8.8/10 Excellent! (1,030 reviews)
"Neat"

Reviewed on Aug 24, 2025

Grand Hyatt Tampa Bay
See all 16,042 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 lively bars.

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

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 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
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

$37
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.