Pinebrook Estates Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 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

Top Holiday Package Deals in Pinebrook Estates

Price found within the past 48 hours. Click for updated prices.
ChartHouse Clearwater Beach Marina Hotel

ChartHouse Clearwater Beach Marina Hotel

2 out of 5
Price was CA $1,057, price is now CA $755 per person
CA $755
per person
Sep 20 - Sep 23
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.6/10 Exceptional! (1,206 reviews)
Hotel was so clean, great staff, and super close to the beach and so many restaurants.

Reviewed on Jul 10, 2026

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Price was CA $2,427, price is now CA $1,601 per person
CA $1,601
per person
Sep 23 - Sep 30
found 12 hours ago
Roundtrip flight included
Toronto (YYZ) to Tampa (TPA)
9.6/10 Exceptional! (1,057 reviews)
There was a problem with the toilet in the master bedroom running all night, both nights. They tried to fix it but was unsuccessful for both nights.

Reviewed on Jul 9, 2026

CW Hotel

CW Hotel

4 out of 5
Price was CA $1,971, price is now CA $1,357 per person
CA $1,357
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
No reviews
We had such a great stay at the CW Resort in Clearwater! The pool area was beautiful and relaxing, the views were amazing, and the entire property was very clean and well maintained. It was the perfect place to unwind and enjoy a Florida getaway. We would definitely stay here again!

Reviewed on Jul 8, 2026

The Avalon Club

The Avalon Club

4 out of 5
Price was CA $1,787, price is now CA $1,267 per person
CA $1,267
per person
Sep 27 - Oct 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
9.4/10 Exceptional! (564 reviews)
If you are thinking of booking the Avalon club it is definitely worth it I highly recommend

Reviewed on Jul 8, 2026

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Price was CA $1,522, price is now CA $1,127 per person
CA $1,127
per person
Aug 23 - Aug 30
found 17 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Tampa (TPA)
8.6/10 Excellent! (2,353 reviews)
Is very well kept, super clean and neat , very helpful

Reviewed on Jul 9, 2026

Where to stay in Pinebrook Estates

Find the best Pinebrook Estates areas and neighborhoods for the activities you enjoy most. Learn more about Pinebrook Estates
A beach with people, a city skyline, and a distinctive pink building.

Pass-a-Grille

Discover a quaint beach neighborhood featuring the Pass-a-Grille Historic District and Gulf Beaches Historical Museum. Enjoy walkable attractions like boutiques, an ice cream shop, outdoor art market, and fishing piers around 8th Street.

Find hotels in Pass-a-Grille

Pinebrook Estates 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
The price is CA $307 per night from Aug 9 to Aug 10
CA $307
CA $403 total
Aug 9 - Aug 10
includes taxes & fees
9.4/10 Exceptional! (3,509 reviews)
"Great property and location. Parking and limited dining options were a little problematic. Everything else was great and we had a wonderful time."

Reviewed on Jul 9, 2026

Wyndham Grand Clearwater Beach
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave Clearwater Beach FL
The price is CA $228 per night from Aug 9 to Aug 10
CA $228
CA $314 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (2,802 reviews)
"Went for two days with my son and we had a blast! Room was comfortable and clean. We rented beach chairs a bit expensive but worth it and relaxed in the clean white sand. The hotel had a liquor cart that drove around and made delicious drinks. Lots of dining options across the street and the starbucks ..."

Reviewed on Jul 10, 2026

Hilton Clearwater Beach Resort & Spa
RumFish Beach at TradeWinds

RumFish Beach at TradeWinds

4 out of 5
6000 Gulf Blvd St. Pete Beach FL
Fully refundableReserve now, pay when you stay
The price is CA $228 per night from Aug 9 to Aug 10
CA $228
CA $346 total
Aug 9 - Aug 10
includes taxes & fees
8.2/10 Very good! (2,130 reviews)
"The room was great. Wished we had a toaster though. Everything else was sufficient. We loved our view of the beach. Drawers needed fixing on the dresser for our clothes, couldn't close a couple of them. When we asked the staff about a certain activity, no one knew much and told us to download the ..."

Reviewed on Jul 9, 2026

RumFish Beach at TradeWinds
See all 16,297 properties in Pinebrook Estates
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
Family Vacations
Family Vacations

Frequently asked questions

How much does a Pinebrook Estates vacation package cost?
From as low as CA $755, you can tailor make your Pinebrook Estates package. Simply bundle flights, hotels and car rentals and we'll reward you with discounts.
How do I get a cheap travel package to Pinebrook Estates?
One of the easiest ways to save cash (and time) is to combine your bookings with Expedia. Hotels, flights, activities and rental cars — we've got it all. Select a combination that best suits you and watch your savings pile up. Of course, a package deal is never a one-size-fits-all. That's why we offer more than 550 partner airlines and 1,000,000 hotel options globally, which lets you customize your Pinebrook Estates vacation.
Where should I stay in Pinebrook Estates?
Stay close to the action. Many people like to book hotels within easy reach of popular sights, like Largo Mall, Fairway Village Golf Course and AirHeads Trampoline Arena.
How far in advance should I book my Pinebrook Estates vacation?
To land rock-bottom prices, book as early as you can. Air carriers typically release flights, along with some of the lowest fares, up to a year prior to departure. Hotels, car rental and experiences should also be booked early so you can have the pick of the bunch. If you're in need of a last-minute getaway in Pinebrook Estates, there are always lots of great deals on Expedia. Book your escape today!
What does an Expedia Pinebrook Estates travel package include?
With Expedia, you can select a combination of car rentals, flights and hotels to create your perfect Pinebrook Estates package. Once you've made your booking, you can add on the fun stuff like sightseeing tours and activities. Don't forget — the more you bundle, the more discounts you'll get!
What should I know before booking a Pinebrook Estates travel package?
A package can be easier on the credit card than individually booking all you need for your adventure. For example, combine your flights, hotels and rental cars and score big savings. No matter your vacation goals, there's bound to be a package to suit your budget.
Can I choose my airline with a Pinebrook Estates Expedia vacation package?
You sure can. We have more than 550 partner airlines globally, so select the carrier that best suits your needs.
If I'm not able to travel, can I cancel my Pinebrook Estates vacation package?
Whether it's your hotel, flight or rental car, you can cancel and rebook it. Booked your Pinebrook Estates vacation package in the last 24 hours? You may be able to make changes at no cost. If it's been longer than that, you may incur a charge from your airline, hotel or car rental company. For further information, look up our Customer Service Portal. We'll help you each step of the way.

Things to do

Sunset Celebration Cruise on Tropics Boat Tours

Sunset Celebration Cruise on Tropics Boat Tours

CA $53
per adult
92% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
Starlite Infinity Evening Yacht Cruise Clearwater

Starlite Infinity Evening Yacht Cruise Clearwater

CA $52
per adult
90% of travellers recommend
Starlite Infinity Evening Yacht Cruise Clearwater
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key

CA $95
per adult
100% of travellers recommend
St. Petersburg, FL: 4-Hour Catamaran Cruise to Egmont Key
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.