Highpoint Vacations from $535

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Delray House With Hot tub & Game Room

Delray House With Hot tub & Game Room

3.5 out of 5
Palm River-Clair Mel
Save 100% on your flight
Price was $1,158, price is now $535 per person
$535
per person
Feb 21 - Feb 27
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
2/10 (2 reviews)
Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,323, price is now $588 per person
$588
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Family Home Tampa

Family Home Tampa

2 out of 5
Forest Hills
Price was $1,644, price is now $774 per person
$774
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
7.6/10 Good! (4 reviews)
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $1,015, price is now $558 per person
$558
per person
Mar 11 - Mar 18
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Excellent customer service

Reviewed on Dec 14, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $3,145, price is now $1,734 per person
$1,734
per person
Mar 7 - Mar 14
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
Yet another wonderful stay with spotless rooms, fantastic views, and a great staff!

Reviewed on Dec 30, 2025

Where to stay in Highpoint

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

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
$241 nightly
The price is $272 total per night from Jan 4 to Jan 5
$272 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (2,941 reviews)
Great time! Amazing views!

Reviewed on Dec 27, 2025

Wyndham Grand Clearwater Beach
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
$190 nightly
The price is $215 total per night from Jan 11 to Jan 12
$215 total
Jan 11 - Jan 12, 2026
Total with taxes and fees
8/10 Very Good! (2,369 reviews)
Amenities

Reviewed on Dec 25, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd Tampa FL
Fully refundableReserve now, pay when you stay
$189 nightly
The price is $215 total per night from Jan 2 to Jan 3
$215 total
Jan 2 - Jan 3, 2026
Total with taxes and fees
8.6/10 Excellent! (2,482 reviews)
The staff was VERY pleasant & accommodating, the property was clean and aesthetically appealing, we will be sure to return. Thank you for a great stay.

Reviewed on Dec 29, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 16,552 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Highpoint

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the marina in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

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

St. Petersburg - Clearwater Beaches
Clearwater Beach

Clearwater Beach

4.5/5(44 reviews)

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

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$29
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

$32
per adult
90% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$28
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
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.