Old Southeast Vacations from $344

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Your Old Southeast Vacation

Take the stress out of planning your next getaway with an Old Southeast vacation package. Take in the sights and sounds of this wonderful neighborhood and experience everything it has to offer. Your trip to Old Southeast wouldn't be complete without a visit to major attractions nearby such as Salvador Dali Museum, Tropicana Field and Sunken Gardens. No matter what your dream Old Southeast vacation looks like, you can turn it into reality with Expedia.

The Latest Old Southeast Vacation Packages

Price found within the past 48 hours. Click for updated prices.
voco Sarasota by IHG

voco Sarasota by IHG

3.5 out of 5
Central Sarasota
Save 100% on your flight
Price was $554, price is now $344 per person
$344
per person
Nov 8 - Nov 11
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

FUSION Resort Waterfront Suites

FUSION Resort Waterfront Suites

3.5 out of 5
Save 100% on your flight
Price was $2,313, price is now $1,269 per person
$1,269
per person
Dec 27 - Jan 3
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.2/10 Wonderful! (1,068 reviews)
Have stayed here a couple times now and would definitely go back. Love the vibes. Only thing that was a bummer is that my daughter and I love using the complimentary bikes to ride around town. However, the bikes are in pretty rough shape. If doable, I would consider maybe replacing the bikes.

Reviewed on Oct 7, 2025

Ocean Club Treasure Island Hotel

Ocean Club Treasure Island Hotel

4 out of 5
Sunshine Beach
Save 100% on your flight
Price was $748, price is now $466 per person
$466
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.6/10 Exceptional! (635 reviews)
Excellent room and facility . Clean and exactly like online pictures .

Reviewed on Oct 9, 2025

Wyndham Grand Clearwater Beach

Wyndham Grand Clearwater Beach

4 out of 5
Save 100% on your flight
Price was $1,175, price is now $739 per person
$739
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (2,661 reviews)
We enjoyed the property and closeness to the beach. Restaurants were walkable. Pool bar food could be upgraded but found the remainder of the dinning options suitable. We had a great time and would recommend.

Reviewed on Oct 7, 2025

The Avalon Club

The Avalon Club

4 out of 5
Save 100% on your flight
Price was $1,037, price is now $659 per person
$659
per person
Nov 13 - Nov 16
found 1 day ago
Roundtrip non-stop flight included
Boston (BOS) to Tampa (TPA)
9.4/10 Exceptional! (456 reviews)
Clean, quite, nice staff

Reviewed on Oct 6, 2025

Where to stay in Old Southeast

Find the best Old Southeast areas and neighborhoods for the activities you enjoy most. Learn more about Old Southeast
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

Old Southeast Hotel Deals

Hotel Tampa Riverwalk

Hotel Tampa Riverwalk

4 out of 5
200 N Ashley Dr, Tampa, FL
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $166 total per night from Oct 19 to Oct 20
$166 total
Oct 19 - Oct 20
Total with taxes and fees
6.8/10 (1,680 reviews)
"Great stay, dj on the pool very nice, clean rooms nice staff"

Reviewed on Oct 5, 2025

Hotel Tampa Riverwalk
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
$109 nightly
The price is $123 total per night from Oct 26 to Oct 27
$123 total
Oct 26 - Oct 27
Total with taxes and fees
7.6/10 Good! (1,010 reviews)
"The valet parking at this hotel is ridiculously expensive. Park at Camden Pier carpark directly behind the hotel for a third of the price. Very handy for the Rowdies ground which is opposite. Loved our stay here."

Reviewed on Oct 6, 2025

Hilton St. Petersburg Bayfront
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
$216 nightly
The price is $244 total per night from Oct 19 to Oct 20
$244 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,454 reviews)

Reviewed on Oct 6, 2025

RumFish Beach at TradeWinds
See all 17,134 properties in Old Southeast
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 Old Southeast

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

Stunning view of dolphins in St. Petersburg, Florida

Dolphin Racer Speedboat Adventure

$28
per adult
92% of travellers recommend
Dolphin Racer Speedboat Adventure
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
Madeira Beach: Pirate Adventure Cruise with Beer and Wine

Madeira Beach: Pirate Adventure Cruise

$42
per adult
100% of travellers recommend
Madeira Beach: Pirate Adventure Cruise
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.