Highpoint Vacation Packages 2026 from $800

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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.

Innisbrook Resort

Save 100% on your flight

$800

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

8.4/10 Very Good! (1,004 reviews)

Ocean Club Treasure Island Hotel

Sunshine Beach

Save 100% on your flight

$1,093

per person

Dec 19 - Dec 24

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.6/10 Exceptional! (1,252 reviews)

First time staying at Ocean Club and it was great. The unit was spacious and the balcony view was amazing. We will definitely stay there again on our next Treasure Island trip!

Reviewed on Oct 19, 2026

Captiva Beach Resort

South Village

Save 100% on your flight

$862

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,312 reviews)

Cedar Cove Resort and Cottages

Save 100% on your flight

$1,446

per person

Jan 9 - Jan 16

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (604 reviews)

Beautiful old florida style resort Beautiful rooms comfortable beds right on the powdery white sand beach and turquoise water

Reviewed on Oct 18, 2026

CW Resort

Save 100% on your flight

$1,419

per person

Dec 26 - Dec 30

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (204 reviews)

Property was clean and beds were very comfortable. Friendly Staff and views are amazing. Would definitely stay again.

Reviewed on Oct 19, 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

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 - Clearwater Beaches.

A sunset over the ocean with a person paddleboarding and a floating structure.

Sunshine Beach

If you're spending some time in Sunshine Beach, St. Petersburg - Clearwater Beaches and St. Petersburg Municipal Beach at Treasure Island are top sights worth seeing.

Highpoint Hotel Deals

Wyndham Grand Clearwater Beach

100 Coronado Drive Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$272 nightly

$307 total

Nov 8 - Nov 9

Total with taxes and fees

Hyatt Regency Clearwater Beach Resort and Suites

301 S Gulfview Blvd Clearwater Beach FL

Fully refundableReserve now, pay when you stay

$297 nightly

$335 total

Nov 17 - Nov 18

Total with taxes and fees

The Westin Tampa Bay

7627 W Courtney Campbell Cswy Tampa FL

Fully refundableReserve now, pay when you stay

$155 nightly

$176 total

Oct 25 - Oct 26

Total with taxes and fees

8.6/10 Excellent! (1,642 reviews)

"Clean room"

Reviewed on Oct 19, 2026

See all 17,156 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.