Highpoint Vacation Packages 2026 from $657

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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.

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$657

per person

Nov 18 - Nov 21

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$709

per person

Nov 14 - Nov 18

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (584 reviews)

Excellent location. Helpful friendly staff. Beach was fantastic. Will return!

Reviewed on Sep 2, 2026

Tropical Beach Resorts

South Village

Save 100% on your flight

$912

per person

Oct 20 - Oct 27

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (5,792 reviews)

Our room (Specialty Room) was clean and roomy. The furnishings were new and the kitchen was updated with a kitchenette and a stainless steel refrigerator. The bathroom was a bit dated but had a nice closet and drawers in the vanity. Parking was a bit of an issue, as space is limited. Restaurants are a 3 minute walk away from where our room was with several options. We only wish our room hadn't been the farthest from the beach, as I was not aware the property was spread out as it was. There was a nice pool nearby, but we decided to avoid the family's with their young children. Still overall, we enjoyed our visit.

Reviewed on Sep 2, 2026

CW Resort

Save 100% on your flight

$791

per person

Nov 8 - Nov 14

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (117 reviews)

The Westin Sarasota

Central Sarasota

Save 100% on your flight

$848

per person

Nov 5 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,160 reviews)

n/a

Reviewed on Sep 2, 2026

Where to stay in Highpoint

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

A modern plaza with a large sculpture, palm trees, and a high-rise building in the background.

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.

A beach with people, a city skyline, and a distinctive pink building.

Pass-a-Grille

1 out of top 10 points of interest in this area

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.

Sand Key

1 out of top 10 points of interest in this area

While visiting Sand Key, you might make a stop by sights like Belleair Beach and Sand Key Park.

A beach with people walking along the shore, waves crashing onto the sand, and a city skyline in the background.

Sunset Beach

Sunset Beach is noteworthy for its beaches, and you can make a stop at top attractions like Sunset Beach and St. Petersburg Municipal Beach at Treasure Island.

A coastal city with a large beach, a prominent pink building, and a marina.

Don Cesar

Don Cesar might not have many top sights, but Splash Island Water Park and Pass-a-Grille Beach are two attractions nearby that you can check out.

Highpoint Hotel Deals

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Fully refundableReserve now, pay when you stay

$147 nightly

$167 total

Sep 6 - Sep 7

Total with taxes and fees

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$256 nightly

$290 total

Sep 6 - Sep 7

Total with taxes and fees

9.4/10 Exceptional! (3,820 reviews)

"Our room face the gulf , it was clean and the ded was comfortable, the hotel was very nice and clean and the staff was helpful and friendly."

Reviewed on Sep 3, 2026

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$272 nightly

$308 total

Sep 4 - Sep 5

Total with taxes and fees

9.4/10 Exceptional! (2,305 reviews)

"Me gusto mucho"

Reviewed on Sep 2, 2026

See all 17,169 properties in Highpoint

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.