Highpoint Vacation Packages

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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.

Top Holiday Package Deals in Highpoint

Price found within the past 48 hours. Click for updated prices.
Bay Palms Waterfront Resort - Hotel and Marina

Bay Palms Waterfront Resort - Hotel and Marina

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.4/10 Very Good! (499 reviews)
Great two bedroom suite. Nice sitting area with the grill by the waterfront and small marina. Across the street is beautiful St Pete beach. Reception crew is one of the best I ever met. Thanks Tyrel, Anna, Tanner and Ray. Super fun, friendly, professional and efficient.

Reviewed on May 3, 2024

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (302 reviews)
The hotel was clean and maintained and the staff was super helpful. Any question we had was promptly answered and they even communicated over text messages (which is easier for me). The pool is a bit small but the beach is so close that it's not a big deal. And they provide free beach chairs and an umbrella so it's actually better than the pool in almost every way. Highly recommended and we'll probably come back next year!

Reviewed on Jun. 14, 2024

Thunderbird Beach Resort

Thunderbird Beach Resort

3 out of 5
Save 100% on your flight
per person
Aug. 2 - Aug. 9
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Tampa (TPA)
8.4/10 Very Good! (1,034 reviews)
Great atmosphere with live music, delicious drinks and amazing staff

Reviewed on Jun. 16, 2024

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.8/10 Excellent! (1,000 reviews)
Excellent location,safe.clean

Reviewed on Jun. 10, 2024

Bayview Plaza Waterfront Resort

Bayview Plaza Waterfront Resort

3 out of 5
Belle Vista
Save 100% on your flight
per person
Jul. 17 - Jul. 22
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
8.6/10 Excellent! (450 reviews)
The staff was so accommodating and friendly. I was in for two short nights and arrived at the hotel at 2 AM. They let me grab my keys, go to my room to sleep and come back once awoken to fully checkin.

Reviewed on May 13, 2024

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

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 hotel + flight trips in Pass-a-Grille

Highpoint Hotel Deals

RumFish Beach Resort by TradeWinds
RumFish Beach Resort by TradeWinds
4 out of 5
6000 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $258 per night from Jun. 18 to Jun. 19
CA $258
CA $377 total
includes taxes & fees
Jun 18 - Jun 19
8.2/10 Very Good! (1,023 reviews)
"Will definitely be back. Was a wonderful vacation!"

Reviewed on Jun. 14, 2024

RumFish Beach Resort by TradeWinds
Sirata Beach Resort
Sirata Beach Resort
3 out of 5
5300 Gulf Blvd, St. Pete Beach, FL
Fully refundableReserve now, pay when you stay
The price is CA $213 per night from Jul. 8 to Jul. 9
CA $213
CA $303 total
includes taxes & fees
Jul 8 - Jul 9
7.2/10 Good! (2,273 reviews)
"The location was everything, I really enjoyed the stay."

Reviewed on Jun. 15, 2024

Sirata Beach Resort
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
The price is CA $340 per night from Jun. 23 to Jun. 24
CA $340
CA $432 total
includes taxes & fees
Jun 23 - Jun 24
9.2/10 Wonderful! (1,859 reviews)
"Beautiful location. Nice, friendly, helpful staff. Nice, clean rooms."

Reviewed on Jun. 15, 2024

Wyndham Grand Clearwater Beach
See all 16,977 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.

Explore other types of vacation packages

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Highpoint vacation package cost?
Our Highpoint packages, which start at just CA $1,031, are the easiest way to save precious money. Select your favorite hotels, flights and more to create your dream escape.
How do I get a cheap travel package to Highpoint?
Combining your flight and hotel with Expedia won’t just save you time — it’ll save you a few dollars too. A Highpoint vacation package makes it simple to arrange the ideal trip. With more than 550 airlines all over the world to select from, finding convenient flights that fit your schedule won’t be hard. In addition to that, we’ve got over 1,000,000 hotels globally to select from. Now that’s choice! No matter who you are, Expedia will help show you the world.
Where should I stay in Highpoint?
With fascinating attractions like Tampa Bay Grand Prix and Cove Cay Golf Club in this area, look for a hotel located near them. Feather Sound Country Club is another sight that visitors flock to.
What are the top hotels in Highpoint?
If it’s your very first time in Highpoint, make a reservation at Holiday Inn Express Clearwater East - Icot Center, an IHG Hotel or Intown Suites Extended Stay Clearwater Fl. Both offer comfortable beds and are popular options with many savvy travelers.
How far in advance should I book my Highpoint vacation?
It’s always wise to book early. Airlines generally release flights nearly 12 months in advance, and this is an ideal opportunity to pick up some of the cheapest prices. Boss just told you to take all your vacation days next week? That’s fine too — Expedia are never short of fantastic bargains to send you on the getaway of your dreams, at an affordable price.
What does an Expedia Highpoint travel package include?
Flights, hotels and car rentals — we connect you to all the best deals. All you have to do is pick and choose your ideal combination. Once you’ve made your booking, you can add on the fun stuff like sightseeing activities. Our travel packages make it simple to create an awesome Highpoint escape.
What should I know before booking a Highpoint travel package?
Bundling your bookings into a Highpoint vacation package is the most convenient way to organize your trip. Not only that, you’ll save when you combine your hotels, flights and car rentals. Once you’ve booked, why not add on a tour or an activity?
Can I choose my airline with a Highpoint Expedia vacation package?
Yes, of course. We have more than 550 partner airlines worldwide, so select the carrier that best fits your travel preferences.
If I'm not able to travel, can I cancel my Highpoint vacation package?
It’s impossible to predict what tomorrow might bring, so it’s comforting to know that you can cancel or change your Highpoint vacation package. If your booking was made in the last 24 hours, you may be entitled to a refund. If it’s an older booking, your airline, hotel or car rental company may charge a fee. Visit our Customer Service Portal to find out more.

Discover the most popular places to visit in Highpoint

Image for John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(136 reviews)

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
Image for Tropicana Field

Tropicana Field

4/5(26 reviews)

Catch an event at Tropicana Field during your trip to St. Petersburg. Attend a baseball game or simply enjoy the top-notch restaurants while you're in the area.

Tropicana Field
Image for Fort De Soto Park

Fort De Soto Park

4.5/5(28 reviews)

Admire the vestiges of the fortress, bring your kids to the pirate ship playground and relax on the beaches of this archipelago.

Fort De Soto Park

Things to do

Image for StarLite Majesty Evening Yacht Cruise Clearwater

StarLite Majesty Evening Yacht Cruise Clearwater

CA $43
Per adult
86% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
Image for 2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

CA $47
Per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
Image for Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar

CA $81
Per adult
100% of travellers recommend
Tiki Boat - Clearwater - The Only Authentic Floating Tiki Bar
See all activities in St. Petersburg - Clearwater

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.