Gulf Highlands Vacations from $417

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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.
Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $651, price is now $417 per person
$417
per person
Jan 11 - Jan 15
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,180 reviews)
Excellent location! Friendly staff, clean and updated rooms.

Reviewed on Oct 27, 2025

The Avalon Club

The Avalon Club

4 out of 5
Price was $1,734, price is now $909 per person
$909
per person
Jan 14 - Jan 18
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (466 reviews)
Overall the property was clean; however, it was a great disappointment to see the street light with wires as an ocean view literally right outside your balcony. I also didn’t appreciate upon greeting the staff stressed about the fees instead of stressing what is already included, such as the beach chairs, umbrella etc…

Reviewed on Oct 15, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,276, price is now $1,275 per person
$1,275
per person
Jan 8 - Jan 15
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
The suite was very clean and well maintained. Every suite had a balcony and view of gulf. Living area was small in compared to kitchen and bedrooms. A+ on the bathrooms.

Reviewed on Oct 29, 2025

Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $941, price is now $550 per person
$550
per person
Jan 6 - Jan 13
found 2 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
Close to downtown safety harbor, oldsmar and Clearwater, the perfect retreat being close to everything but not in the heart of it all.

Reviewed on May 12, 2025

Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Save 100% on your flight
Price was $913, price is now $568 per person
$568
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (4,474 reviews)
100 Stars plus by far a very amazing Hotel and completely worth the money you won't be disappointed

Reviewed on Oct 30, 2025

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
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Bayonet Point

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.

Find hotels in Bayonet Point

Gulf Highlands Hotel Deals

Motel 6 Spring Hill, FL - Weeki Wachee

Motel 6 Spring Hill, FL - Weeki Wachee

2 out of 5
6172 Commercial Way, Spring Hill, FL
Fully refundableReserve now, pay when you stay
$50 nightly
The price is $56 total per night from Nov 9 to Nov 10
$56 total
Nov 9 - Nov 10
Total with taxes and fees
7.2/10 Good! (1,227 reviews)
Clean friendly staff

Reviewed on Oct 26, 2025

Motel 6 Spring Hill, FL - Weeki Wachee
Main River Mermaid Sleeps 8 kayaks for everyone. Gulf access for scalloping

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

Spring Hill
9.8/10 Exceptional! (295 reviews)
Stunning home- just beautiful. Loved everything about it, so tastefully decorated and clean. Kitchen is beautiful and fun to cook in.Comfortable beds. Screened in porch was wonderful, with a great tv. Kayaks in great shape that were easy to get in and out of the water with the steps. We used the ...

Reviewed on Oct 22, 2025

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

Innisbrook Resort

3.5 out of 5
36750 Us Highway 19 N, Palm Harbor, FL
$195 nightly
The price is $220 total per night from Nov 2 to Nov 3
$220 total
Nov 2 - Nov 3
Total with taxes and fees
8.2/10 Very Good! (1,008 reviews)
Good

Reviewed on Oct 26, 2025

Innisbrook Resort
See all 1,951 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Gulf Highlands

Low tide sunset over the #GulfofMexico

Werner Boyce Salt Springs State Park

4/5(4 reviews)

You can take time to visit Werner Boyce Salt Springs State Park during your travels to Port Richey. Stroll along the waterfront or visit the shops in this family-friendly area.

Werner Boyce Salt Springs State Park

SunCruz Port Richey Casino

Why not try your luck with a visit to SunCruz Port Richey Casino during your travels in Port Richey? Amble around this family-friendly area's waterfront, or seek out the golf courses.

SunCruz Port Richey Casino

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.

Beacon Woods Golf Course

Things to do

2 Hours Kayak Eco Tour in Tarpon Springs

2 Hours Kayak Eco Tour in Tarpon Springs

$54
per adult
2 Hours Kayak Eco Tour in Tarpon Springs
Tarpon Springs Train Depot at Night

Tarpon Springs: Ghost and Haunted History Tour

$40
per adult
Tarpon Springs: Ghost and Haunted History Tour
Sponge Dock Stroll

Sponge Dock Stroll

$52
per adult
100% of travellers recommend
Sponge Dock Stroll
See all activities in Port Richey
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.