Southside Vacations from $421
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Your Southside Vacation
Immerse yourself in the wonder of this picturesque neighborhood with a Southside vacation package. From its shopping and nature to its walking, there's something for every visitor. Wondering what to do and see during your trip to Southside? The Avenues and Latitude 30 are just a couple of nearby attractions that shouldn't be missed. Expedia is here to help put your travel plans into action. Book your ideal Southside vacation today.
The Latest Southside Vacation Packages
Price found within the past 48 hours. Click for updated prices.
Tricove Inn & Suites
Southside
$421
per person
Nov 11 - Nov 15
found 13 hours ago
Roundtrip non-stop flight included
Boston (BOS) to Jacksonville (JAX)
7.4/10 Good! (1,002 reviews)
We stayed at Tricove Inns & Suites for one night, and overall, it was a pleasant experience. All the staff members were friendly, helpful, and welcoming. Although the hotel looks a bit old, the rooms were spacious and comfortable. It was a nice stay, and we appreciated the friendly service. A good option for a short stay!
Reviewed on Oct 9, 2026
Hammock Beach Golf Resort & Spa
$1,321
per person
Dec 27 - Jan 3
found 7 hours ago
Roundtrip flight included
Philadelphia (PHL) to Jacksonville (JAX)
8.8/10 Excellent! (1,011 reviews)
If you want a relaxing vacation where once you check in and not have to worry about anything then this is the place for you. The grounds were beautiful. The staff is extremely nice and considerate and helpful. The room was beyond what we were expecting with the cleanliness and how spacious it was. We enjoyed the trip so much that we are already planning another one! Thank you Hammock Beach for an awesome vacation!
Reviewed on Oct 11, 2026
Where to stay in Southside
Find the best Southside areas and neighborhoods for the activities you enjoy most. Learn more about Southside
Downtown Jacksonville
2 out of top 10 points of interest in this area
Historic core with major corporations, Downtown Jacksonville offers diverse culinary and nightlife experiences at The Elbow. Explore attractions like Florida Theatre, TIAA Bank Field, and museums, while enjoying convenient transportation options.
Amelia City
While visiting Amelia City, you might make a stop by sights like American Beach and Fernandina Beach.
Oceanfront
If you're spending some time in Oceanfront, Oceanfront Park and Northeast Florida Beaches are top sights worth seeing.
American Beach
If you're spending some time in American Beach, American Beach and Spanish Quarter Village are top sights worth seeing.
Sawgrass
Visitors to Sawgrass like its beaches and riverfront, and Mickler Beach is a sight worth a stop.
Southside Hotel Deals
Wyndham Garden Jacksonville
4660 Salisbury Road Jacksonville FL
Fully refundableReserve now, pay when you stay
$75 nightly
$85 total
Oct 14 - Oct 15
Total with taxes and fees
7.8/10 Good! (2,107 reviews)
"The room was ok but looked old or a little run down. The bathroom was worse and the The shower was not clean. Do not eat at the attached bar unless you want to interact with a shady bartender that won't shut up and let you eat in peace. I highly recommend you avoid this hotel unless you are ..."
Reviewed on Oct 12, 2026
Hyatt Studios Jacksonville/St Johns Town Center
11565 Village crossing Drive, Jacksonville FL
Fully refundableReserve now, pay when you stay
$116 nightly
$132 total
Oct 29 - Oct 30
Total with taxes and fees
9.4/10 Exceptional! (225 reviews)
"Great place and close to everything. The only thing was that housekeeping was not every day"
Reviewed on Oct 11, 2026
Midtown Lodge
4141 Philips Hwy Jacksonville FL
Fully refundableReserve now, pay when you stay
$53 nightly
$60 total
Oct 18 - Oct 19
Total with taxes and fees
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.
Stay near popular Southside attractions
St. Johns Town Center
8.8/10 (3,607 reviews)
With a visit to St. Johns Town Center, a favorite shopping spot in Jacksonville, you can enjoy some retail therapy. Stroll along the area's beautiful beaches or experience its great live music.
Orange Park Place Shopping Center
During your visit to Jacksonville, you can do some window-shopping at Orange Park Place Shopping Center. Experience the area's acclaimed theater scene or attend a sporting event.
Merill Road Shopping Center
During your visit to Jacksonville, you can do some window-shopping at Merill Road Shopping Center. Experience the area's lively festivals and acclaimed theater scene.
Dog Wood Park of Jacksonville
10.0/10 (2 reviews)
After visiting Dog Wood Park of Jacksonville, make a plan to see the other sights and activities in Jacksonville. Amble around this family-friendly area's beautiful beaches and enjoy its top-notch restaurants.
Hands on Children's Museum
10.0/10 (1 review)
You can take time to visit Hands on Children's Museum during your travels to Jacksonville. Experience the area's great live music and lively festivals.
San Jose Plaza Shopping Center
During your visit to Jacksonville, you can find the perfect gifts to bring home at San Jose Plaza Shopping Center. Experience the area's great live music and lively festivals.
Crabtree Park
Crabtree Park is just one of the places to see in Jacksonville, so why not enjoy the other things to explore during your travels? Discover the top-notch restaurants and great live music in this family-friendly area.
Things to do
Half-Day City Tour in Downtown Jacksonville
$114
per adult
100% of travellers recommend
1 Hour Jet Ski Rental in Jacksonville, FL Jax Jet Skis
$145
per traveler
90% of travellers recommend
The Escape Game at St. John's Town Center in Jacksonville
$42
per adult
100% of travellers recommend
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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.