Southside Vacations from $445
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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.
Omni Amelia Island Resort & Spa
Save 100% on your flight
Price was $1,576, price is now $1,044 per person
$1,044
per person
Feb 1 - Feb 8
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.6/10 Excellent! (1,008 reviews)
Loved Amelia Island and the Omni resort. Friendly staff, clean, and lots to do!
Reviewed on Nov 12, 2025
Hampton Inn Jacksonville Beach/Oceanfront
Save 100% on your flight
Price was $1,080, price is now $726 per person
$726
per person
Feb 1 - Feb 8
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
9.2/10 Wonderful! (2,500 reviews)
Staff was great , the beds were very uncomfortable, one made so much noise every time you moved that it kept me up all night, I asked front desk to address it but nothing happened but very nice other wise . Would love to stay again if the beds were better.
Reviewed on Nov 15, 2025
The Villas of Amelia Island
Save 100% on your flight
Price was $912, price is now $629 per person
$629
per person
Feb 1 - Feb 8
found 6 hours ago
Roundtrip flight included
Boston (BOS) to Jacksonville (JAX)
8.4/10 Very Good! (1,104 reviews)
The staff was courteous but I felt like Jack on the Titanic when I let them know I was staying in the villas as opposed to the main building :-)
The room was nice, but there was only one tiny trashcan for a three day stay — so that was an issue as well.
Reviewed on Nov 11, 2025
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
4/5(845 area reviews)
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.
Southside Hotel Deals
Embassy Suites by Hilton Jacksonville Baymeadows
9300 Baymeadows Road, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $135 total per night from Nov 23 to Nov 24
$135 total
Nov 23 - Nov 24
Total with taxes and fees
8.4/10 Very Good! (1,242 reviews)
Yes
Reviewed on Nov 15, 2025
Wyndham Garden Jacksonville
4660 Salisbury Road Jacksonville FL
Fully refundableReserve now, pay when you stay
$70 nightly
The price is $79 total per night from Nov 23 to Nov 24
$79 total
Nov 23 - Nov 24
Total with taxes and fees
7.6/10 Good! (1,764 reviews)
Close to my destination, staff was wonderful great stay
Reviewed on Nov 14, 2025
Homewood Suites by Hilton Jacksonville-South/St. Johns Ctr.
10434 Midtown Pkwy, Jacksonville, FL
Fully refundableReserve now, pay when you stay
$103 nightly
The price is $117 total per night from Nov 23 to Nov 24
$117 total
Nov 23 - Nov 24
Total with taxes and fees
8.2/10 Very Good! (1,003 reviews)
clean room. Friendly staff. You
Reviewed on Nov 12, 2025
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.
Discover the most popular places to visit in Southside
St. Johns Town Center
4.5/5(1,158 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 riverfront or experience its acclaimed theater scene.
HCA Florida Memorial Hospital
4/5(31 reviews)
Though HCA Florida Memorial Hospital might be what brings you to town, perhaps you'll have a chance to explore more of Jacksonville while you are here.
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.
Things to do
1 Hour Jet Ski Rental in Jacksonville, FL Evolution Jetsports
$140
per traveler
90% 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.