Highpoint Vacations from $388

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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.
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $617, price is now $388 per person
$388
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (4,612 reviews)
Breakfast was fresh and good , hot coffee was fresh, and tasty.

Reviewed on Nov 16, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $1,499, price is now $775 per person
$775
per person
Feb 4 - Feb 8
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Very nice stay. Would stay there again.

Reviewed on Nov 12, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,492, price is now $844 per person
$844
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
New York (JFK) to Tampa (TPA)
19.2/10 Exceptional! (707 reviews)
The unit was excellent. The price for these accommodations was very reasonable. It had two bedrooms and two full bathrooms. There was a washed and dryer, full well stocked kitchen, living/ dining area and a large patio. The appliances were spotless and looked brand new. Everything worked perfectly. There are large screen easy to use TV's in each bedroom and the living area. The staff was super friendly and helpful. The swimming pool was very well kept and clean. The outdoor spa was exceptional. Parking was great. We have been traveling since 2000 in many locations around the USA and other countries. These were by far the best accommodations we have experienced. Wonderful experience and an exceptional staff! When we return to this area we will stay here.

Reviewed on Nov 14, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $791, price is now $489 per person
$489
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
18.4/10 Exceptional! (1,001 reviews)
Great front desk staff ! Very kind and helpful

Reviewed on Oct 27, 2025

Hilton Garden Inn Sarasota - Bradenton Airport

Hilton Garden Inn Sarasota - Bradenton Airport

3 out of 5
Save 100% on your flight
Price was $815, price is now $523 per person
$523
per person
Jan 24 - Jan 28
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,006 reviews)
Would definitely stay here again .

Reviewed on Oct 31, 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

DoubleTree by Hilton Tampa Rocky Point Waterfront

DoubleTree by Hilton Tampa Rocky Point Waterfront

4 out of 5
3050 N Rocky Point Dr W Tampa FL
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $139 total per night from Nov 20 to Nov 21
$139 total
Nov 20 - Nov 21
Total with taxes and fees
8.2/10 Very Good! (1,004 reviews)
The breakfast was good and the food was fresh.

Reviewed on Nov 13, 2025

DoubleTree by Hilton Tampa Rocky Point Waterfront
The Westin Tampa Bay

The Westin Tampa Bay

4 out of 5
7627 W Courtney Campbell Cswy Tampa FL
Fully refundable
$135 nightly
The price is $153 total per night from Nov 23 to Nov 24
$153 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,046 reviews)
👍

Reviewed on Nov 15, 2025

The Westin Tampa Bay
Hotel South Tampa & Suites

Hotel South Tampa & Suites

3 out of 5
3314 S Dale Mabry Hwy Tampa FL
Fully refundableReserve now, pay when you stay
$80 nightly
The price is $91 total per night from Nov 18 to Nov 19
$91 total
Nov 18 - Nov 19
Total with taxes and fees
8.6/10 Excellent! (1,581 reviews)
Nice

Reviewed on Nov 12, 2025

Hotel South Tampa & Suites
See all 16,398 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)

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 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 Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
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

$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.