Highlands Vacation Packages 2026 from $469

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The Latest Highlands Vacation Packages

Price found within the past 48 hours. Click for updated prices.

BAY INN

Temple Crest

Save 100% on your flight

$469

per person

Nov 18 - Nov 23

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

6.2/10 (576 reviews)

The Fold Hotels Indian Shores

Save 100% on your flight

$623

per person

Nov 10 - Nov 17

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,014 reviews)

Such a nice place! Walking distance to the beach. The staff are very friendly and responsive. Our room was very clean and modern. Great stay!!

Reviewed on Sep 10, 2026

Cedar Cove Resort and Cottages

Save 100% on your flight

$724

per person

Oct 31 - Nov 3

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (591 reviews)

Un lugar muy bonito y cómodo para disfrutar en familia lo único es que los sofácama no son cómodos yo tuve que comprar un colchón y solo hay un parqueo por habitación el personal es muy amable la pasamos bien

Reviewed on Sep 16, 2026

The Avalon Club

Save 100% on your flight

$1,885

per person

Nov 23 - Nov 30

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (595 reviews)

Perfect location on the beach and close to many shops and restaurants.

Reviewed on Sep 17, 2026

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$1,016

per person

Nov 19 - Nov 24

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,004 reviews)

The staff was very helpful and friendly. Room was available for early check in which was so convenient. Personal touches were appreciated, thanks Tiffany.

Reviewed on Sep 16, 2026

Where to stay in Highlands

Find the best Highlands areas and neighborhoods for the activities you enjoy most. Learn more about Highlands

A wooden pier extending into a calm sea with a sandy beach in the foreground.

Gulf Shores

Gulf Shores might not have many top sights, but Hudson Beach and Beacon Woods Golf Course are two attractions nearby that you can check out.

A boat with colorful flags, a pier, and a crowd of people.

Bayonet Point

1 out of top 10 points of interest in this area

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.

A beach with sand dunes and tall grasses at sunset.

Hudson Beach Estates

1 out of top 10 points of interest in this area

Though Hudson Beach Estates might not have many top sights, you can venture to the surrounding area to see attractions like Hudson Beach and Beacon Woods Golf Course.

A harbor with multiple sailboats anchored in calm waters under a cloudy sky.

Sea Ranch

While Sea Ranch isn't home to many top sights, Hudson Beach and Beacon Woods Golf Course are some notable places to visit nearby.

Signal Cove

When in Signal Cove, you can plan a visit to Hudson Beach and Beacon Woods Golf Course, some noteworthy sights in the nearby area.

Highlands Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

6172 Commercial Way Spring Hill FL

Fully refundableReserve now, pay when you stay

$44 nightly

$49 total

Oct 12 - Oct 13

Total with taxes and fees

7.4/10 Good! (1,582 reviews)

"Always a great place to stay"

Reviewed on Sep 18, 2026

Mermaid Life Main River Sleeps 8 kayaks for everyone. Gulf access for scalloping

Spring Hill FL

10/10 Exceptional! (332 reviews)

"The house was very cute and clean. The location was great. It was easy to put our boat in the water and explore the river and the gulf. The river was beautiful. We enjoyed kayaking and morning coffees on the dock swing watching the gorgeous nature all around."

Reviewed on Sep 18, 2026

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Quality Inn & Suites Tarpon Springs South

38724 US Highway 19 North Tarpon Springs FL

Fully refundable

$83 nightly

$94 total

Oct 19 - Oct 20

Total with taxes and fees

See all 1,869 properties in Highlands

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.