Highpoint Vacations from $1,242

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Your Highpoint Vacation

Say bye-bye to the stress of planning and hello to a Highpoint vacation package. With everything organized before you take off, you can focus on discovering the best of this city, starting with Downtown Dunedin, which is great for shopping, walking and gift and craft shops. Any trip to Highpoint needs a well-crafted itinerary. Fill yours with big-name attractions like Ruth Eckerd Hall, Eddie C. Moore Softball Complex and Bright House Field. A few clicks is all it takes to put together the perfect Highpoint vacation on Expedia.

The Latest Highpoint Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Cedar Cove Resort and Cottages

Cedar Cove Resort and Cottages

3 out of 5
Save 100% on your flight
Price was $1,986, price is now $1,242 per person
$1,242
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (506 reviews)
Everything was perfect

Reviewed on May 15, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,090, price is now $1,312 per person
$1,312
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (932 reviews)
Nice location Easy check in and out Great ocean view and walkable to beach Nice pool Easy to park vehicle on property Some of the staff were super friendly. Room was lovely but beds need to be replaced. In room washer and dryer did not work properly.

Reviewed on May 17, 2026

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $2,097, price is now $1,326 per person
$1,326
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (3,219 reviews)
Didn’t like the water pressure. Every thing else was fine.

Reviewed on May 16, 2026

The Residences at Siesta Key Beach by Hyatt Vacation Club

The Residences at Siesta Key Beach by Hyatt Vacation Club

3.5 out of 5
South Village
Save 100% on your flight
Price was $2,781, price is now $1,763 per person
$1,763
per person
Jun 17 - Jun 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.8/10 Exceptional! (344 reviews)
It was a fantastic and beautiful property among the best I’ve stayed in on vacation. However, I wish they cleared the beach daily of the seaweed like the public beaches did and sprayed for the love bugs because both things made it difficult to take full advantage of the ocean and property and its amenities respectively.Apparently, early May is peak for the Sargassum seaweed and love bugs. The pool chairs, patio, game room, fire pit and other public places were fully covered with bugs some days so we couldn’t even use them.

Reviewed on May 14, 2026

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $3,011, price is now $1,963 per person
$1,963
per person
Jun 27 - Jul 4
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
Great experience! The staff is very kind. The only issue was the living room sofa was very noisy. Would definitely stay again!

Reviewed on May 12, 2026

Where to stay in Highpoint

Find the best Highpoint areas and neighborhoods for the activities you enjoy most. Learn more about Highpoint
Pass-a-Grille

Pass-a-Grille

1 out of top 10 points of interest in this area
5/5(26 area reviews)

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Highpoint Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$316 nightly
The price is $357 total per night from May 25 to May 26
$357 total
May 25 - May 26
Total with taxes and fees
9.4/10 Exceptional! (3,240 reviews)
Great

Reviewed on May 17, 2026

Wyndham Grand Clearwater Beach
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
$147 nightly
The price is $167 total per night from May 24 to May 25
$167 total
May 24 - May 25
Total with taxes and fees
8.6/10 Excellent! (1,302 reviews)
Pool was closed. You are obligated to pay for parking, you choose between $35 for valet or $27 self park per day. Front desk advised it is $27 per day, in which resets at midnight, therefore for one overnight stay self park will cost you $54. I booked a room with full bay view, high floor. Little ...

Reviewed on May 16, 2026

The Westin Tampa Bay
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
$204 nightly
The price is $230 total per night from May 25 to May 26
$230 total
May 25 - May 26
Total with taxes and fees
8.2/10 Very Good! (2,617 reviews)
It has been our third time at the Hilton in Clearwater. The service, food, and location were exceptional. We will definitely be back

Reviewed on May 16, 2026

Hilton Clearwater Beach Resort & Spa
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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.
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Discover the most popular places to visit in Highpoint

Aerial view of the pink-tinged waters reflecting the vibrant sunset hues next to the John's Pass Village & Boardwalk, Treasure Island, Florida, United States.

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 marina in this family-friendly area, or check out its lively bars.

John's Pass Village & Boardwalk
Florida. St Pete Beach FL. Summer vacations. Ocean beach, Hotels and Resorts in US. Blue-turquoise color of salt water. American Coast or shore line in Gulf of Mexico. St Petersburg Clearwater Florida

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
White sand and palm trees in 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

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$37
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$40
per adult
90% 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.