Gulf Blue Vacations - Vacation Rentals in Southside

Sunny apartment in walkable San Marco! From US $174
         

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1.0 (1 Review)
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  • Pet Friendly
Corporate Suite Shoppe From US $193
         

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10.0 (2 Reviews)
Apartment
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AWESOME/LUXURY/PERFECT LOCATION/PVT HOME @SE/Mandarin From US $193
         

10.0 (46 Reviews)
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  • Pet Friendly
Pet Friendly Studio with Tons of 5 Star Reviews From US $183
         

10.0 (45 Reviews)
House
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  • Pet Friendly
Adorable Condo - 2 blocks from San Marco Square! From US $249
         

10.0 (41 Reviews)
Condo
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  • Pet Friendly
Family-Friendly Beach Retreat Heated Pool By Mayo From US $402
         

10.0 (36 Reviews)
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  • Pet Friendly

Luxury Places to Stay in Southside

Over 1323+ Luxury Places to Stay in or Near Southside
Chateau Coquina From US $3,744
         

New
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  • Pet Friendly
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Private owner looking for a responsible tenant. From US $1,879
         

"Waterfront Paradise" Dock, Pool, Boathouse From US $1,625
         

10.0 (4 Reviews)
House
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  • TV
  • Balcony/Terrace
Marriott Jacksonville From US $1,440
         

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8.4 (157 Reviews)
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Hilton Garden Inn Jacksonville Downtown Southbank From US $1,280
         

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7.8 (340 Reviews)
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  • Pet Friendly
Three Oaks Manor Pool Riverfront From US $1,162
         

10.0 (8 Reviews)
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Hampton Inn Jacksonville South/I-95 at JTB From US $1,010
         

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8.6 (203 Reviews)
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Top-Rated Vacation Rentals with a Pool in Southside

Over 488+ Top-Rated Vacation Rentals with a Pool in or Near Southside
1 King Bed | Non-Smoking, Kitchen From US $76
         

10.0 (31 Reviews)
Apartment
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  • Pet Friendly
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1 Full Bed | ADA/Tub/Non-Smoking/Kitchen From US $76
         

10.0 (31 Reviews)
Apartment
  • Air Conditioner
  • Pet Friendly
  • Pool
1 Queen Bed | Non-Smoking, Kitchen, Sofa-Bed From US $76
         

10.0 (29 Reviews)
Apartment
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  • Pet Friendly
  • Pool
1 King Bed | Suite, Nsmk, Kitchen, Sofa-Bed From US $82
         

10.0 (25 Reviews)
Apartment
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  • Pet Friendly
  • Pool
2 Full Beds | Non-Smoking, Kitchen From US $82
         

10.0 (21 Reviews)
Apartment
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  • Pet Friendly
  • Pool
~Fresca Familia Sleeps 8 Heated Pool & Shopping~ From US $396
         

10.0 (12 Reviews)
House
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  • Pet Friendly
~Dapper Duck Sleeps 12 Cool Pool & Billiards~ From US $514
         

10.0 (10 Reviews)
House
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  • Pet Friendly

Pet-Friendly Vacation Rentals in Southside

Over 521+ Pet-Friendly Vacation Rentals in or Near Southside
Cush Jax Baymeadows Ranch, Close to Everything! From US $286
         

10.0 (15 Reviews)
House
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Stylish Condo - 2 block from San Marco From US $177
         

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New
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Large Vacation Homes & Villas in Southside

Over 134+ Large Vacation Homes & Villas in or Near Southside
3BR Townhome/Close to Mayo and Beaches! From US $379
         

10.0 (2 Reviews)
House
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  • View
Family Retreat Pool Table Arcade Heart of San Marco From US $359
         

10.0 (5 Reviews)
House
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  • Pet Friendly
Charming 3BR Townhome Centrally located in Jacksonville From US $258
         

Golden Spike Oasis I Heated Pool From US $401
         

10.0 (2 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • TV
Sunshine Escape for up to 16: 7BR/6BA, Pool & Gym From US $898
         

10.0 (1 Review)
Apartment
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  • Pet Friendly

Wheelchair Accessible Vacation Homes in Southside

Over 269+ Wheelchair Accessible Vacation Homes in or Near Southside
Paradise Escape: Stylish 3BR/2BA with Pool & Gym From US $375
         

10.0 (6 Reviews)
Apartment
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  • Pet Friendly
Lux Pool Home Mins to Mayo Beach UNF Spine andPain From US $373
         

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10.0 (1 Review)
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Hyatt Studios Jacksonville/St Johns Town Center From US $134
         

Beachy Oasis: Posh 2BR/2BA with Pool & Gym From US $319
         

10.0 (5 Reviews)
Apartment
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  • Pet Friendly
Comfy Modern King Bed Pool Near Mayo Town Center From US $213
         

10.0 (5 Reviews)
Apartment
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Tropical Retreat: Luxe 2BR/2BA with Pool & Gym From US $298
         

10.0 (3 Reviews)
Apartment
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  • Pet Friendly
Modern King Bed Deerwood Pool Gym Downtown Jax I95 From US $230
         

10.0 (3 Reviews)
Apartment
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Southside Vacation Rentals and Airbnb Places to Stay Under $200

Over 791+ Southside Vacation Rentals and Airbnb Places to Stay Under $200
4 Mi to Dtwn Jacksonville: Chic Home w/Porch! From US $166
         

10.0 (8 Reviews)
House
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  • Pet Friendly
Beautiful Days From US $85
         

10.0 (6 Reviews)
Apartment
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Family Home 5 Mi to Riverwalk & Jaguars Games! From US $187
         

Beautiful 2BR Townhome Close to beach/Mayo Clinic From US $196
         

10.0 (5 Reviews)
House
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  • TV
  • Security/Safety
Spacious Jax Home Near Riverwalk & All Beaches From US $179
         

10.0 (5 Reviews)
House
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  • TV
  • Balcony/Terrace
Stylish Remodeled Townhouse – Entire Home - Great Location! From US $178
         

Serenity Retreat 1BD Lux King in Southeast Jax with Balcony and Lake View From US $154
         

10.0 (4 Reviews)
Apartment
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  • Security/Safety
  • Bedding/Linens

Instantly Bookable Vacation Homes in Southside

Over 685+ Instantly Bookable Vacation Homes in or Near Southside
ENTIRE HOUSE 3/2 GREAT FOR FAMILY n From US $259
         

10.0 (15 Reviews)
House
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La Casita by Amarelys and lazaro From US $274
         

10.0 (9 Reviews)
House
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  • Designated Smoking Area
Private Pool Getaway 5min Beach Sleeps 9 From US $472
         

10.0 (5 Reviews)
House
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  • Pet Friendly
privacy paradise From US $314
         

10.0 (5 Reviews)
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  • Parking
  • TV

About Southside Vacation Rentals

With more than 1332 Southside vacation rentals, we can help you find a place to stay. These rentals, including vacation rentals, Gulfbluevacations and other short-term private accommodations, have top-notch amenities with the best value, providing you with comfort and luxury at the same time. Get more value and more room when you stay at a rental property in Southside.

Looking for last-minute deals, or finding the best deals available for cottages, condos, private villas, and large vacation homes? With Gulfbluevacations Southside, you have the flexibility of comparing different options of various deals with a single click. Looking for a rental by owner with the best swimming pools, hot tubs, allows pets, or even those with huge master suite bedrooms and have large screen televisions? You can find vacation rentals by owner, and other popular Airbnb-style properties in Southside. Places to stay near Southside are 796.16 ft² on average, with prices averaging US $264 a night.

Gulfbluevacations makes it easy and safe to find and compare vacation rentals in Southside with prices often at a 30-40% discount versus the price of a hotel. Just search for your destination and secure your reservation today.

Top Rental Accommodation Types in Southside

Type Count
Vacation Homes 603
Holiday Apartments 481
Hotels 174
Cottages 7
Resorts 3
B&B 2
Others 2
Villas 2
Cabin Rentals 1

Use these Quick Filters to Find a Vacation Rental in Southside

Pro Tip: Gulfbluevacations makes it easy to compare the best listings on Gulfbluevacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Gulfbluevacations homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Southside.

Weather in Southside

View the weather forecast for Southside before booking your Southside Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Southside Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Southside?
How many vacation rentals are available in Southside?

Currently, the total number of properties listed in 2026 is over 1332 in the Southside area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Southside.