Harbor Hills Vacations from $582

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Your Harbor Hills Vacation

Planning your next adventure just got a whole lot simpler with a vacation package to Harbor Hills. Immerse yourself in all this neighborhood has to offer while creating nice memories along the way. When it's time to see the sights, you'll find a lot of awesome attractions nearby including Largo Mall, Florida Botanical Gardens and Pinellas Trail. Visit one, two or all during your trip to Harbor Hills. Whatever your ideal Harbor Hills vacation looks like, you can turn it into reality with Expedia.

The Latest Harbor Hills Vacation Packages

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

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,552, price is now $582 per person
$582
per person
Jan 24 - Jan 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
No reviews
Kompose Boutique Hotel

Kompose Boutique Hotel

3 out of 5
Price was $1,429, price is now $671 per person
$671
per person
Feb 6 - Feb 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (4,624 reviews)
The hotel was excellent

Reviewed on Dec 14, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $2,632, price is now $1,513 per person
$1,513
per person
Feb 21 - Feb 28
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,001 reviews)
AC was really good. Good size TV, in good position to watch from the sofa or bed. Staff very helpful. Plenty of free parking. Great location for Ringling Museum and other attractions, and nice walking areas without driving. Breakfast was very good and well worth getting included. It is a coupon for $35 per too, which was more than enough if two.

Reviewed on Nov 21, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $2,334, price is now $1,380 per person
$1,380
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,000 reviews)
This place was a great surprise ! So friendly so helpful ! Great location and rooms super clean . Tons of amenities too! Will definitely stay again

Reviewed on Dec 8, 2025

SkyBeach Resort

SkyBeach Resort

4 out of 5
Greater Pinellas Point
Save 100% on your flight
Price was $1,074, price is now $651 per person
$651
per person
Mar 8 - Mar 13
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (417 reviews)
I didn’t know about the $50 resort fee! Place is great!

Reviewed on Dec 10, 2025

Where to stay in Harbor Hills

Find the best Harbor Hills areas and neighborhoods for the activities you enjoy most. Learn more about Harbor Hills
Downtown St. Petersburg featuring outdoor art

Downtown St. Petersburg

1 out of top 10 points of interest in this area

Come here for the beaches and sunshine and discover much more in this Florida city with something for all ages and tastes.

Find hotels in Downtown St. Petersburg

Harbor Hills Hotel Deals

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
100 Coronado Drive Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$255 nightly
The price is $288 total per night from Jan 4 to Jan 5
$288 total
Jan 4 - Jan 5, 2026
Total with taxes and fees
9.4/10 Exceptional! (2,874 reviews)
Yes

Reviewed on Dec 8, 2025

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
Fully refundableReserve now, pay when you stay
$174 nightly
The price is $196 total per night from Dec 21 to Dec 22
$196 total
Dec 21 - Dec 22
Total with taxes and fees
8/10 Very Good! (2,355 reviews)
Yes great view

Reviewed on Dec 13, 2025

Hilton Clearwater Beach Resort & Spa
Hotel Alba, Tapestry Collection by Hilton

Hotel Alba, Tapestry Collection by Hilton

4 out of 5
5303 W Kennedy Blvd Tampa FL
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $157 total per night from Dec 22 to Dec 23
$157 total
Dec 22 - Dec 23
Total with taxes and fees
8.6/10 Excellent! (2,443 reviews)
Due to an unexpected medical injury, I stayed at this hotel for 14 days to recovery. Every staff member I came in contact with was kind, compassionate, and concern about my health recovery. Their actions and words were outstanding and helped in my daily improvement to eventually travel home to Illinois. ...

Reviewed on Dec 13, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 14,279 properties in Harbor Hills
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 Harbor Hills

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

4.5/5(1,625 reviews)

You can do some window-shopping at John's Pass Village & Boardwalk during your stay in Madeira Beach. Stroll along the marina in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

5/5(5 reviews)

Why not spend a lazy afternoon at St. Petersburg - Clearwater Beaches during your trip to St. Petersburg - Clearwater?

St. Petersburg - Clearwater Beaches
Clearwater Beach

Clearwater Beach

4.5/5(44 reviews)

Why not spend a lazy afternoon at Clearwater Beach during your trip to Clearwater Beach? Wander the clear-water beaches or discover the area's beautiful sunsets.

Clearwater Beach

Things to do

The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$29
per adult
90% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
View of the StarLite Sapphire Yacht on St. Pete Beach

StarLite Sapphire Evening Yacht St. Pete Beach

$32
per adult
90% of travellers recommend
StarLite Sapphire Evening Yacht St. Pete Beach
Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$28
per adult
94% of travellers recommend
Dolphin Racer Speedboat Adventure
See all activities in St. Petersburg - Clearwater
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.