Highlands Vacations from $308
Book a Hotel + Flight or Car together to unlock savings
The Latest Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Clearwater Suites
Save 100% on your flight
Price was $507, price is now $308 per person
$308
per person
Nov 8 - Nov 11
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Super convenient, clean, and right across the street from the beach. Staff was very friendly
Reviewed on Aug 25, 2025
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $675, price is now $361 per person
$361
per person
Oct 22 - Oct 26
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,006 reviews)
Great bar and staff. Close to everything. Have stayed here a couple times. Clean. All around great stay
Reviewed on Aug 31, 2025
Ocean Club Treasure Island Hotel
Save 100% on your flight
Price was $1,035, price is now $597 per person
$597
per person
Nov 15 - Nov 19
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Loved the condo, the access to the beach, in unit laundry, and convenience of the location. Gym and beach bar on site, would definitely come back!
Reviewed on Aug 30, 2025
The Westin Sarasota
Central Sarasota
Save 100% on your flight
Price was $1,697, price is now $1,026 per person
$1,026
per person
Nov 15 - Nov 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,061 reviews)
It was very noisy. Inside, toilets, doors & cleaning staff. Outside, basic traffic, green car every night
Reviewed on Aug 29, 2025
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Bayonet Point
1 out of top 10 points of interest in this area
3.5/5(171 area reviews)
Shopping, waterfront views, and restaurants highlight some of the notable features of Bayonet Point. Make a stop by Beacon Woods Golf Course while you're exploring.
Highlands Hotel Deals
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way, Spring Hill, FL
Fully refundableReserve now, pay when you stay
$60 nightly
The price is $67 total per night from Sep 7 to Sep 8
$67 total
Sep 7 - Sep 8
Total with taxes and fees
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North, Tarpon Springs, FL
Fully refundableReserve now, pay when you stay
$89 nightly
The price is $101 total per night from Sep 7 to Sep 8
$101 total
Sep 7 - Sep 8
Total with taxes and fees
Innisbrook Resort
36750 Us Highway 19 N, Palm Harbor, FL
$199 nightly
The price is $225 total per night from Sep 1 to Sep 2
$225 total
Sep 1 - Sep 2
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.
Discover the most popular places to visit in Highlands
Hudson Beach
4/5(32 reviews)
Why not spend a carefree afternoon at Hudson Beach during your travels in Hudson? Amble around the area's parks or visit its shops.
Show Palace Dinner Theater
You can enjoy a show at Show Palace Dinner Theater during your stay in Hudson. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.
Beacon Woods Golf Course
Enjoy a round of golf in Hudson at Beacon Woods Golf Course. Amble around this family-friendly area's waterfront and enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.