Highpoint Vacations from $513
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The Latest Highpoint Vacation Packages
Price found within the past 48 hours. Click for updated prices.
- Hibiscus Suites - Gateway to Siesta Key
Sep 17 - Sep 20Hibiscus Suites - Gateway to Siesta Key + Flight
Sarasota3 nights2.5 star property8.6/10 - Excellent (2,372 reviews)"Really enjoyed staying at Hibiscus Suites. It was really close to events we had planned as well as restaurants and Siesta Key Beach. Even though hotel is located on busy street, the traffic was not heard from room. I would highly recommend staying."Reviewed July 17, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - SRQ • 1 stop SRQ - BOS • 1 stop$709$513found 1 day agoper traveler - Cedar Cove Resort and Cottages
Sep 17 - Sep 20Cedar Cove Resort and Cottages + Flight
Holmes Beach3 nights3.0 star property9.2/10 - Wonderful (557 reviews)"Loved this property. Perfect place for a quiet vacation. Sits right on the beach and the views were amazing. The owner and staff were very nice. Booked through Expedia and it was a little expensive but would stay there again."Reviewed July 17, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - SRQ • 1 stop SRQ - BOS • 1 stop - CW Hotel
Aug 26 - Aug 31CW Hotel + Flight
Clearwater Beach5 nights4.0 star property10/10 - Exceptional (6 reviews)"We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!"Reviewed July 8, 2026Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - Wyndham Grand Clearwater Beach
Aug 26 - Aug 31Wyndham Grand Clearwater Beach + Flight
Clearwater Beach5 nights4.0 star property9.4/10 - Exceptional (3,542 reviews)Roundtrip • Boston (BOS) - Tampa (TPA)BOS - TPA • Nonstop TPA - BOS • 1 stop - Ocean Club Treasure Island Hotel
Sep 18 - Sep 21Ocean Club Treasure Island Hotel + Flight
Sunshine Beach3 nights4.0 star property9.6/10 - Exceptional (1,090 reviews)"Wonderful place to stay. Only wish there was a more comfortable chair in the living room area. Clean, excellent space to relax and enjoy your time at the beach. Would be nice to have a fan on the balcony for those very hot nights."Reviewed July 17, 2026Roundtrip • New York (JFK) - Tampa (TPA)JFK - TPA • Nonstop TPA - JFK • Nonstop$1,064$743found 2 days agoper traveler
Highpoint Hotel Deals
Sleep Inn Clearwater - St Petersburg
Sleep Inn Clearwater - St Petersburg2.5 star property
Feather Sound, 1.8 mi from Highpoint
9.2 out of 10, Wonderful, (1,192 reviews)
9.2/10
Wonderful
(1,192 reviews)
"Not a great area of town. Hotel and beds were run down. Staff was very nice. The hotel shuttle runs 24 hours which is great."
$74 nightly
The price is $84
$84 total
Aug 5 - Aug 6
Total with taxes and fees
Comfort Inn & Suites St. Pete - Clearwater International Airport
Comfort Inn & Suites St. Pete - Clearwater International Airport2.5 star property
1.9 mi from Highpoint
8.2 out of 10, Very Good, (1,315 reviews)
8.2/10
Very Good
(1,315 reviews)
"Breakfast was good. Check in was easy. Overall, a good experience."
$86 nightly
The price is $97
$97 total
Jul 21 - Jul 22
Total with taxes and fees
Hampton Inn & Suites Clearwater/St. Petersburg-Ulmerton Road, FL
Hampton Inn & Suites Clearwater/St. Petersburg-Ulmerton Road, FL3.0 star property
1.8 mi from Highpoint
8.8 out of 10, Excellent, (1,002 reviews)
8.8/10
Excellent
(1,002 reviews)
"Easy to find, easy check in, comfortable."
$106 nightly
The price is $120
$120 total
Jul 27 - Jul 28
Total with taxes and fees
Home2 Suites By Hilton Clearwater St. Petersburg Ulmerton Rd
Home2 Suites By Hilton Clearwater St. Petersburg Ulmerton Rd3.0 star property
1.4 mi from Highpoint
9.4 out of 10, Exceptional, (204 reviews)
9.4/10
Exceptional
(204 reviews)
$114 nightly
The price is $129
$129 total
Jul 26 - Jul 27
Total with taxes and fees
Holiday Inn St Petersburg N - Clearwater by IHG
Holiday Inn St Petersburg N - Clearwater by IHG3.0 star property
Feather Sound, 2.1 mi from Highpoint
8.0 out of 10, Very Good, (1,001 reviews)
8.0/10
Very Good
(1,001 reviews)
"Clean, affordable, staff friendly , close to airport."
$91 nightly
The price is $103
$103 total
Jul 26 - Jul 27
Total with taxes and fees
Fairfield Inn & Suites by Marriott Clearwater
Fairfield Inn & Suites by Marriott Clearwater3.0 star property
3.6 mi from Highpoint
9.2 out of 10, Wonderful, (1,000 reviews)
9.2/10
Wonderful
(1,000 reviews)
"Staff"
$110 nightly
The price is $124
$124 total
Aug 2 - Aug 3
Total with taxes and fees
Holiday Inn Express Hotel & Suites Clearwater/Us 19 N by IHG
Holiday Inn Express Hotel & Suites Clearwater/Us 19 N by IHG2.5 star property
3.8 mi from Highpoint
8.6 out of 10, Excellent, (1,000 reviews)
8.6/10
Excellent
(1,000 reviews)
"Breakfast was always good. If you were out late parking was hard to find. I do wish all the elevators were working but that's no big deterrent from staying there!"
$92 nightly
The price is $104
$104 total
Aug 3 - Aug 4
Total with taxes and fees
7.6 out of 10, Good, (1,005 reviews)
7.6/10
Good
(1,005 reviews)
"10 out of 10 every time I stay here!!! ✌️❤️🙂"
$87 nightly
The price is $98
$98 total
Jul 30 - Jul 31
Total with taxes and fees
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.
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.