Highlands Vacations from $655
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The Latest Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG
Central Sarasota
Save 100% on your flight
Price was $974, price is now $655 per person
$655
per person
Jul 24 - Jul 30
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,006 reviews)
Centrally located and within walking distance of Downtown Sarasota. Room was clean and comfortable. Dinner in the lobby lounge was excellent for both the service and food. I would stay there again.
Reviewed on May 2, 2026
The Avalon Club
Save 100% on your flight
Price was $2,078, price is now $1,408 per person
$1,408
per person
Jul 9 - Jul 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (534 reviews)
Great experience! The staff is very kind. The only issue was the living room sofa was very noisy. Would definitely stay again!
Reviewed on May 12, 2026
Where to stay in Highlands
Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands
Gulf Shores
Gulf Shores might not have many top sights, but Hudson Beach and Cow Creek are two attractions nearby that you can check out.
Highlands Hotel Deals
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
$54 nightly
The price is $60 total per night from May 21 to May 22
$60 total
May 21 - May 22
Total with taxes and fees
7.4/10 Good! (1,490 reviews)
Great price
Reviewed on May 13, 2026
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping
Spring Hill FL
10/10 Exceptional! (314 reviews)
This house is in the perfect location on the main river. The house and kitchen are well appointed for any length of stay. We saw so many manatees, a river otter and a pair of dolphins. The weather was rainy one day and the screened porch was the ideal location to sit and relax while still enjoying ...
Reviewed on Apr 12, 2026
Rodeway Inn Port Richey North
11810 Us Highway 19 Port Richey FL
Fully refundableReserve now, pay when you stay
$67 nightly
The price is $74 total per night from May 30 to May 31
$74 total
May 30 - May 31
Total with taxes and fees
7.8/10 Good! (1,004 reviews)
never coming back again worse hotel
Reviewed on May 10, 2026
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(33 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.
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.
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.
Things to do
Clear Kayak Tours in Weeki Wachee
$90
per adult
100% of travellers recommend
Audio Guide to New Port Richey's History and Quirky People
$7
per adult
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.