Gulf Highlands Vacations from $428

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Your Gulf Highlands Vacation

Your next big adventure is calling out to you with a vacation package to Gulf Highlands. Excitement, fun and good times — you're sure to find it in this neighborhood. Want to explore the sights during your trip to Gulf Highlands? Make sure you check out nearby attractions like Hudson Beach, Werner Boyce Salt Springs State Park and Gulf View Square. Don't just dream it — do it! Reserve your ultimate Gulf Highlands vacation with Expedia and get to where you're going your way.

The Latest Gulf Highlands Vacation Packages

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

The Fold Hotels Indian Shores

Save 100% on your flight

$428

per person

Nov 7 - Nov 11

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (1,018 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

$669

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9.2/10 Wonderful! (603 reviews)

CW Resort

Save 100% on your flight

$870

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (188 reviews)

The Avalon Club

Save 100% on your flight

$1,093

per person

Dec 5 - Dec 12

found 1 day ago

Roundtrip flight included

Boston (BOS) to Tampa (TPA)

9.4/10 Exceptional! (605 reviews)

voco Sarasota by IHG

Central Sarasota

Save 100% on your flight

$553

per person

Nov 7 - Nov 10

found 1 day ago

Roundtrip non-stop flight included

Boston (BOS) to Tampa (TPA)

9/10 Wonderful! (1,000 reviews)

Where to stay in Gulf Highlands

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

A marina with boats docked, surrounded by residential buildings and a large hotel.

Jasmine Estates

While Jasmine Estates isn't home to many top sights, Gulf View Square and Regal Hollywood - Port Richey are some notable places to visit nearby.

A calm water body reflecting trees and sky, surrounded by dense vegetation and tall palm trees.

Marthas Vineyard

Though Marthas Vineyard might not have many top sights, you can venture to the surrounding area to see attractions like Gulf View Square and Werner Boyce Salt Springs State Park.

Regency Park

If you're looking for some top things to see and do in Regency Park and surrounding area, you can visit Gulf View Square and Regal Hollywood - Port Richey.

A sunset over a calm lake with a dock and trees silhouetted against the sky.

Embassy Hills

Embassy Hills might not have many top sights, but Gulf View Square and Regal Hollywood - Port Richey are two attractions nearby that you can check out.

Jasmine Lakes

While Jasmine Lakes isn't home to many top sights, Regal Hollywood - Port Richey and Gulf View Square are some notable places to visit nearby.

Gulf Highlands Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

6172 Commercial Way Spring Hill FL

Fully refundableReserve now, pay when you stay

$53 nightly

$59 total

Oct 18 - Oct 19

Total with taxes and fees

7.4/10 Good! (1,581 reviews)

"Great place great people great prices 😁"

Reviewed on Oct 1, 2026

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

Spring Hill FL

10/10 Exceptional! (333 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

$80 nightly

$91 total

Oct 8 - Oct 9

Total with taxes and fees

See all 2,192 properties in Gulf 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.