
Vacation rentals in Southside, Jacksonville
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Top-rated vacation rentals in Southside, Jacksonville
Guests agree: these stays are highly rated for location, cleanliness, and more.
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Popular amenities for Southside, Jacksonville vacation rentals
Other great vacation rentals in Southside, Jacksonville
Top guest favorite

Cottage in St. Augustine
4.99 out of 5 average rating, 118 reviewsDriftwood Cottage by the Sea
Guest favorite

Home in Jacksonville
4.9 out of 5 average rating, 145 reviewsThe Pink Cabana
Superhost

Apartment in St. Augustine
4.87 out of 5 average rating, 143 reviewsWalk to the Beach 2
Guest favorite

Townhouse in St. Augustine
4.9 out of 5 average rating, 133 reviewsParadise Retreat*Vilano Beach*Sand & Ocean Breeze
Guest favorite

Home in St. Augustine
4.89 out of 5 average rating, 112 reviews"The Coastal House" Water Views and a Golf cart!
Guest favorite

Home in St. Augustine
4.92 out of 5 average rating, 103 reviewsnew 4 bedroom home, 2 master-suites and pool
Superhost

Home in St. Augustine
4.86 out of 5 average rating, 102 reviewsSweet Sandcastle Vacations: A Luxury Beach Getaway
Guest favorite

Home in Beaches
4.92 out of 5 average rating, 126 reviewsLuxury Beach Getaway w/ Heated Pool & Game Room
Quick stats about vacation rentals in Southside, Jacksonville
Total rentals
1.3K properties
Total number of reviews
39K reviews
Family-friendly rentals
710 properties are a good fit for families
Pet-friendly rentals
550 properties allow pets
Rentals with a pool
450 properties have a pool
Rentals with dedicated workspaces
810 properties have a dedicated workspace
Destinations to explore
- Rentals with an EV charger Southside
- Private suite rentals Southside
- Rentals with beach access Southside
- Waterfront rentals Southside
- Rentals with outdoor seating Southside
- Rentals with a hot tub Southside
- Condo rentals Southside
- Townhouse rentals Southside
- Guesthouse rentals Southside
- Smoking-friendly rentals Southside
- Rentals with lake access Southside
- Fitness-friendly rentals Southside
- Rentals with a patio Southside
- Pet-friendly rentals Southside
- Rentals with a washer and dryer Southside
- House rentals Southside
- Family-friendly rentals Southside
- Rentals with breakfast Southside
- Rentals with a fireplace Southside
- Kid-friendly rentals Southside
- Apartment rentals Southside
- Rentals with a fire pit Southside
- Rentals with pools Southside
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- Boneyard Beach
- Old A1A Beach
- Kathryn Abbey Hanna Park
- TIAA Bank Field
- Amelia Island State Park
- Palm Harbor Golf Club
- Guana Reserve Middle Beach
- Fountain of Youth Archaeological Park
- Crescent Beach
- Pablo Creek Club
- Driftwood Beach
- St. Augustine Alligator Farm Zoological Park
- Matanzas Beach
- Eagle Landing Golf Club
- St. Marys Aquatic Center
- Dungeness Beach
- Lightner Museum
- Ravine Gardens State Park
- Butler Beach
- Fort Mose Historic State Park
- North Beach Guana River Preserve
- Little Talbot