Pinebrook Estates Vacations from $416

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Your Pinebrook Estates Vacation

Your next big adventure is calling out to you with a vacation package to Pinebrook Estates. Entertainment, food and nothing but great times — you're bound to find it in this neighborhood. Your trip to Pinebrook Estates wouldn't be complete without a visit to major attractions nearby such as Largo Mall, Fairway Village Golf Course and East Bay Golf Club. Stop dreaming and start doing. When you're ready to book your dream vacation to Pinebrook Estates, Expedia will help you get there.

The Latest Pinebrook Estates Vacation Packages

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
Save 100% on your flight
Price was $632, price is now $416 per person
$416
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (387 reviews)
Seven night stay, staff was friendly and helpful, room was clean and comfortable. Would stay there anytime!

Reviewed on Oct 13, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $2,296, price is now $1,310 per person
$1,310
per person
Dec 26 - Dec 31
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
The place is great, excellent location, close to many outdoor activities, amazing ocean view, staff is very good and attentive to our needs, hotel is clean, parking very convenient, rooms are very nice, clean and confortable. We’ll definitely come back and recommend Ocean Club.

Reviewed on Oct 13, 2025

voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $1,060, price is now $655 per person
$655
per person
Dec 22 - Dec 27
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,003 reviews)
It was nice to have a gym available and it was always empty. Shower was my favorite park, really big and open, bed was super comfy. The elevators were outnof order though and the coffee machine in the room didnt work, but over all it was a pretty nice hotel. One of the nicest ive been too.

Reviewed on Oct 4, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,638, price is now $1,634 per person
$1,634
per person
Dec 29 - Jan 1
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 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

Hibiscus Suites - Gateway to Siesta Key

Hibiscus Suites - Gateway to Siesta Key

2.5 out of 5
Save 100% on your flight
Price was $1,079, price is now $709 per person
$709
per person
Jan 6 - Jan 12
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (2,173 reviews)
Clean, centrally located, excellent customer service.

Reviewed on Oct 5, 2025

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
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

Pinebrook Estates Hotel Deals

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
$127 nightly
The price is $144 total per night from Nov 2 to Nov 3
$144 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (1,039 reviews)
"Great place to stay for an event at the stadium."

Reviewed on Oct 13, 2025

Hilton Tampa Airport Westshore
Hilton Clearwater Beach Resort & Spa

Hilton Clearwater Beach Resort & Spa

4 out of 5
400 Mandalay Ave, Clearwater Beach, FL
$231 nightly
The price is $261 total per night from Oct 26 to Oct 27
$261 total
Oct 26 - Oct 27
Total with taxes and fees
8/10 Very Good! (2,246 reviews)
"Right on the beach with excellent amenities"

Reviewed on Oct 11, 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
$147 nightly
The price is $167 total per night from Oct 26 to Oct 27
$167 total
Oct 26 - Oct 27
Total with taxes and fees
8.6/10 Excellent! (2,262 reviews)
"Rooms were clean. Staff was friendly and hotel is just a great place to stay."

Reviewed on Oct 12, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 15,591 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
Kid Friendly Vacations
Kid Friendly Vacations

Discover the most popular places to visit in Pinebrook Estates

John's Pass Village & Boardwalk

John's Pass Village & Boardwalk

When you visit John's Pass Village & Boardwalk, a popular shopping spot in Madeira Beach, you can browse for souvenirs. Stroll along the beautiful beaches in this family-friendly area, or check out its top-notch restaurants.

John's Pass Village & Boardwalk
Clearwater Beach

Clearwater Beach

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
Beach Walk featuring a sandy beach

St. Petersburg - Clearwater Beaches

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

St. Petersburg - Clearwater Beaches

Things to do

The Tropics Boat at Sunset

Sunset Celebration Cruise on Tropics Boat Tours

$37
per adult
88% of travellers recommend
Sunset Celebration Cruise on Tropics Boat Tours
The StarLite Majesty Cruise Ship in Clearwater, Florida

StarLite Majesty Evening Yacht Cruise Clearwater

$32
per adult
88% of travellers recommend
StarLite Majesty Evening Yacht Cruise Clearwater
2 Hour Sunset Cruise in Clearwater, Florida

2 Hour Sunset Cruise in Clearwater, Florida

$35
per adult
88% of travellers recommend
2 Hour Sunset Cruise in Clearwater, Florida
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.