
Holiday houses in Southside, Jacksonville
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Top-rated holiday rentals in Southside, Jacksonville
Guests agree: these stays are highly rated for location, cleanliness and more.
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Holiday rentals for every style
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Popular amenities for Southside, Jacksonville holiday rentals
Other great holiday rentals in Southside, Jacksonville
Top Guest favourite

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

Home in Lincolnville
4.86 out of 5 average rating, 7 reviewsPalms & Porches Paradise
Guest favourite

Home in Jacksonville
4.9 out of 5 average rating, 143 reviewsThe Pink Cabana
Superhost

Home in St. Augustine
4.68 out of 5 average rating, 34 reviewsCozy Beach House Of Your Dreams
Guest favourite

Home in Jacksonville
4.9 out of 5 average rating, 59 reviewsLovely and spacious Florida get away
Guest favourite

Home in St. Augustine
4.92 out of 5 average rating, 102 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
Top Guest favourite

Townhouse in St. Augustine
4.9 out of 5 average rating, 88 reviewsIsland Breeze in Vilano Beach-5 min walk to beach
Quick stats about holiday 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
- Condo rentals Southside
- Rentals with outdoor seating Southside
- Pet-friendly rentals Southside
- Rentals with a washing machine and dryer Southside
- Apartment rentals Southside
- Rentals with beach access Southside
- Guesthouse rentals Southside
- Kid-friendly rentals Southside
- Rentals with an EV charger Southside
- Rentals with breakfast Southside
- Townhouse rentals Southside
- Fitness-friendly rentals Southside
- Rentals with pools Southside
- Rentals with a fire pit Southside
- House rentals Southside
- Private suite rentals Southside
- Waterfront rentals Southside
- Smoking-friendly rentals Southside
- Rentals with lake access Southside
- Rentals with a patio Southside
- Rentals with a fireplace Southside
- Rentals with a hot tub Southside
- Family-friendly rentals Southside
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- Old A1A Beach
- Boneyard Beach
- Palm Harbor Golf Club
- Kathryn Abbey Hanna Park
- Vilano Beach
- TIAA Bank Field
- Driftwood Beach
- Pablo Creek Club
- Matanzas Beach
- Crescent Beach
- St. Augustine Alligator Farm Zoological Park
- Fountain of Youth Archaeological Park
- Guana Reserve Middle Beach
- Eagle Landing Golf Club
- Amelia Island State Park
- St. Marys Aquatic Center
- Old Salt Park
- Ravine Gardens State Park
- Butler Beach
- Bent Creek Golf Course
- Little Talbot
- Amelia Island Lugar Lindo