Highlands Vacations from $400
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The Latest Highlands Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Hampton Inn Sarasota - I-75 Bee Ridge
Save 100% on your flight
Price was $769, price is now $400 per person
$400
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (317 reviews)
Friendly staff, restaurants next door. Small, but decent gym.
Reviewed on Nov 29, 2025
The Avalon Club
Price was $2,014, price is now $1,046 per person
$1,046
per person
Feb 11 - Feb 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Room was great. Reception awesome. Location awesome. However, the washer stopped working middle of night - resulting in our laundry being stuck (door locked, would not release as water error). We couldn't get fixed. By time maintenance got fixed, we had to check out. TO credit, they mailed our laundry to us, but we needed it the for the next 3 days of our vacaction, and didn't have it available.
Reviewed on Nov 26, 2025
Hilton Garden Inn Sarasota - Bradenton Airport
Save 100% on your flight
Price was $839, price is now $442 per person
$442
per person
Jan 7 - Jan 12
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.2/10 Very Good! (1,002 reviews)
Staff was very friendly and happy to help. The room was clean. The front area was organized, and plenty of snack items were available to purchase.
Reviewed on Nov 24, 2025
Kompose Boutique Hotel
Save 100% on your flight
Price was $1,816, price is now $961 per person
$961
per person
Feb 14 - Feb 21
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
! The hotel is super fancy—very modern and extremely clean. The staff is friendly. Thanks to Valeria, the girl who helped us. The breakfast was super good. We need more hotel like this. ❤️
Reviewed on Nov 30, 2025
Ocean Club Treasure Island Hotel
Sunshine Beach
Save 100% on your flight
Price was $5,624, price is now $3,152 per person
$3,152
per person
Feb 21 - Feb 27
found 1 hour ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (712 reviews)
We loved it will definitely be back
Reviewed on Nov 30, 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
Comfort Inn & Suites New Port Richey Downtown District
6206 US HWY 19 New Port Richey FL
Fully refundableReserve now, pay when you stay
$83 nightly
The price is $93 total per night from Dec 21 to Dec 22
$93 total
Dec 21 - Dec 22
Total with taxes and fees
9.2/10 Wonderful! (1,052 reviews)
The front desk woman was very pleasant. We we were very happy with our room. It was very clean and comfortable.
Reviewed on Nov 26, 2025
Quality Inn & Suites Tarpon Springs South
38724 US Highway 19 North Tarpon Springs FL
Fully refundableReserve now, pay when you stay
$71 nightly
The price is $80 total per night from Dec 7 to Dec 8
$80 total
Dec 7 - Dec 8
Total with taxes and fees
8/10 Very Good! (1,011 reviews)
Great location near the city and clean room , comfortable bed. just less amenities.
Reviewed on Nov 30, 2025
Motel 6 Spring Hill, FL - Weeki Wachee
6172 Commercial Way Spring Hill FL
Fully refundableReserve now, pay when you stay
$31 nightly
The price is $35 total per night from Dec 8 to Dec 9
$35 total
Dec 8 - Dec 9
Total with taxes and fees
7.2/10 Good! (1,259 reviews)
Great
Reviewed on Nov 27, 2025
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.