Charter Oaks Vacations from $438

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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 $693, price is now $438 per person
$438
per person
Dec 4 - Dec 8
found 21 hours ago
Roundtrip non-stop flight included
Minneapolis (MSP) 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

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,350, price is now $740 per person
$740
per person
Jan 3 - Jan 6
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

Hilton St. Petersburg Carillon Park

Hilton St. Petersburg Carillon Park

3.5 out of 5
Price was $847, price is now $506 per person
$506
per person
Jan 9 - Jan 13
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,013 reviews)
The room was spacious, clean, and quite.

Reviewed on Oct 26, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $1,386, price is now $875 per person
$875
per person
Dec 3 - Dec 10
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (669 reviews)
Very clean and very quiet. Staff were very knowledgeable and nice.Unobstructed view of the gorgeous sunsets! Great location. We will be back!!

Reviewed on Oct 26, 2025

Plaza Beach Hotel Beachfront Resort

Plaza Beach Hotel Beachfront Resort

3 out of 5
Save 100% on your flight
Price was $1,202, price is now $792 per person
$792
per person
Jan 2 - Jan 9
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9/10 Wonderful! (1,018 reviews)
This is a small place but the location is great. Beautiful beach with direct access and views from Some Rooms. Conveniently located to stores and restaurants or public transportation. Rooms are clean, beds could’ve been more comfortable. Staff helpful and pleasant. Pool was very nice and clean with a small bar. Overall great place to stay.

Reviewed on Oct 26, 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

Hilton Tampa Airport Westshore

Hilton Tampa Airport Westshore

4 out of 5
2225 N Lois Ave, Tampa, FL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Nov 16 to Nov 17
$127 total
Nov 16 - Nov 17
Total with taxes and fees
8.4/10 Very Good! (1,077 reviews)
Great room

Reviewed on Oct 25, 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
Fully refundableReserve now, pay when you stay
$215 nightly
The price is $242 total per night from Nov 3 to Nov 4
$242 total
Nov 3 - Nov 4
Total with taxes and fees
8/10 Very Good! (2,263 reviews)
Outdoor pool was very cold and uncomfortable.

Reviewed on Oct 22, 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 $158 total per night from Nov 23 to Nov 24
$158 total
Nov 23 - Nov 24
Total with taxes and fees
8.6/10 Excellent! (2,310 reviews)
My overall experience at this hotel was amazing. I give it a 90 out of 100. The only thing I feel like would need improvement is maid service.

Reviewed on Oct 26, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 15,310 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
Kid Friendly Vacations
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)

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

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
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

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.