Charter Oaks Vacations from $378

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Your Charter Oaks Vacation

Book a Charter Oaks vacation package and immerse yourself in the way of life and rhythm of this captivating neighborhood. With all your travel plans taken care of, the only thing you need to focus on here is having an absolute ball. Start your trip to Charter Oaks by visiting nearby attractions such as Eddie C. Moore Softball Complex, Westfield Countryside Mall and Bright House Field. Don't just wish for it — take action! Secure your ultimate Charter Oaks vacation with Expedia and get to where you're going your way.

The Latest Charter Oaks Vacation Packages

Price found within the past 48 hours. Click for updated prices.
Mar Bay Motel &Suites

Mar Bay Motel &Suites

2 out of 5
Save 100% on your flight
Price was $653, price is now $378 per person
$378
per person
Feb 5 - Feb 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (60 reviews)
room was very good clean and comfortable

Reviewed on Dec 7, 2025

Saddlebrook Resort

Saddlebrook Resort

4 out of 5
Wesley Chapel South
Price was $1,257, price is now $566 per person
$566
per person
Feb 17 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
No reviews
The Beachcomber

The Beachcomber

2.5 out of 5
Save 100% on your flight
Price was $1,680, price is now $977 per person
$977
per person
Feb 17 - Feb 22
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8/10 Very Good! (1,005 reviews)
Everything was nice. Beds could be a little higher off the floor , otherwise very nice

Reviewed on Dec 7, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,793, price is now $1,064 per person
$1,064
per person
Feb 23 - Feb 28
found 1 day ago
Roundtrip 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

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $2,360, price is now $1,465 per person
$1,465
per person
Mar 3 - Mar 7
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (481 reviews)
Is excellent hotel. I recommend

Reviewed on Dec 9, 2025

Where to stay in Charter Oaks

Find the best Charter Oaks areas and neighborhoods for the activities you enjoy most. Learn more about Charter Oaks
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

Charter Oaks 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! (2,351 reviews)
All good

Reviewed on Dec 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
Fully refundableReserve now, pay when you stay
$139 nightly
The price is $157 total per night from Dec 21 to Dec 22
$157 total
Dec 21 - Dec 22
Total with taxes and fees
8.6/10 Excellent! (2,424 reviews)
Excellent customer service. Great shuttle bus service.

Reviewed on Dec 8, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 15,532 properties in Charter Oaks
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
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Kid Friendly Vacations

Discover the most popular places to visit in Charter Oaks

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

$32
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
86% 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
92% 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.