Charter Oaks Vacations from $437

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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.
Clearwater Suites

Clearwater Suites

2.5 out of 5
Save 100% on your flight
Price was $711, price is now $437 per person
$437
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (19 reviews)
Estuvimos dos noches en el hotel y nos gustó mucho, todo muy limpio lo mismo dentro de la habitación que en la piscina, la atención excelente, la playa super serca del hotel es solo cruzar la calle, está ubicado céntrico, una experiencia satisfactoria la esatacia, lo volvería a repetir!!!

Reviewed on Aug 31, 2025

GALAXY HOTEL

GALAXY HOTEL

3.5 out of 5
Downtown St. Petersburg
Save 100% on your flight
Price was $953, price is now $564 per person
$564
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
8.6/10 Excellent! (362 reviews)
Randy was really nice and helpful

Reviewed on Aug 29, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,677, price is now $998 per person
$998
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,592 reviews)
Clean, peaceful, walkable.

Reviewed on Aug 31, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Save 100% on your flight
Price was $1,145, price is now $688 per person
$688
per person
Nov 6 - Nov 10
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (609 reviews)
Loved the condo, the access to the beach, in unit laundry, and convenience of the location. Gym and beach bar on site, would definitely come back!

Reviewed on Aug 30, 2025

Embassy Suites by Hilton Sarasota, FL

Embassy Suites by Hilton Sarasota, FL

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $972, price is now $611 per person
$611
per person
Oct 2 - Oct 9
found 1 day ago
Roundtrip flight included
Boston (BOS) to Tampa (TPA)
8.8/10 Excellent! (1,596 reviews)
Good service, nice atmosphere — it’s worth coming here to relax. The food at the restaurant was good, and the breakfast as well.

Reviewed on Sep 1, 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 St. Petersburg Bayfront

Hilton St. Petersburg Bayfront

4 out of 5
333 1st St S, St. Petersburg, FL
Fully refundableReserve now, pay when you stay
$112 nightly
The price is $127 total per night from Sep 7 to Sep 8
$127 total
Sep 7 - Sep 8
Total with taxes and fees
Hilton St. Petersburg Bayfront
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
$221 nightly
The price is $250 total per night from Sep 7 to Sep 8
$250 total
Sep 7 - Sep 8
Total with taxes and fees
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
$149 nightly
The price is $169 total per night from Sep 2 to Sep 3
$169 total
Sep 2 - Sep 3
Total with taxes and fees
8.6/10 Excellent! (2,057 reviews)
"My stay was awesome"

Reviewed on Aug 29, 2025

Hotel Alba, Tapestry Collection by Hilton
See all 14,759 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

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 lively bars.

John's Pass Village & Boardwalk
The sunset behind the lifeguard tower in combination with a bit of filtering made this image quite unique. #LifeAtExpedia

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 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
Little Toot Dolphin Adventure at Clearwater Beach

Little Toot Dolphin Adventure at Clearwater Beach

$37
per adult
96% of travellers recommend
Little Toot Dolphin Adventure at Clearwater Beach
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.