
Guesthouse holiday rentals in Southside, Jacksonville
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Top-rated Guesthouses in Southside, Jacksonville
Guests agree: These guesthouses are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Southside, Jacksonville guesthouses
Family-Friendly guesthouses

Cozy Cottage Studio, Walk to Beach

Charming Villa with Private Beach Access

Pool House-2 Bdr/1Ba Apt-Pool-Sleeps 5-Pets OK

Lovely Guesthouse in the Up-and-Coming Springfield

Graceful Southern Guesthouse + Outdoor Living Area

The Funk House-A Retreat
Guesthouses with a patio

Beach Bliss Hideaway: 1bd Gem!

The Little House

Bold City Bungalow

Tropical guest house a few blocks from the beach

Adorable 2 Bedroom Cottage

Comfortable and Gently Disney.

Transforms, Full Kitchen/bath, Centrally located

The Treehouse - Murray Hill
Guest house rentals with a washing machine and dryer

Charming Pet-Friendly Guesthouse in Avondale

Downtown Jacksonville Historic District

Palm Valley Pool House

Stylish Bungalow Near Dining,Parks & Entertainment

Spacious 2/1 in historic walkable neighborhood

Serene Getaway at the White House

Il Rifugio waterfront retreat on the ICW by Mayo!

Boho Bungalow
Quick stats about guesthouse rentals in Southside, Jacksonville
Total rentals
20 properties
Nightly prices starting at
$77 AUD before taxes and fees
Total number of reviews
3K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wi-Fi availability
20 properties include access to Wi-Fi
Destinations to explore
- Rentals with beach access Southside
- House rentals Southside
- Rentals with a hot tub Southside
- Townhouse rentals Southside
- Rentals with pools Southside
- Waterfront rentals Southside
- Kid-friendly rentals Southside
- Rentals with breakfast Southside
- Rentals with an EV charger Southside
- Family-friendly rentals Southside
- Private suite rentals Southside
- Smoking-friendly rentals Southside
- Rentals with a fire pit Southside
- Pet-friendly rentals Southside
- Rentals with a patio Southside
- Apartment rentals Southside
- Rentals with a fireplace Southside
- Condo rentals Southside
- Rentals with a washing machine and dryer Southside
- Fitness-friendly rentals Southside
- Rentals with lake access Southside
- Rentals with outdoor seating Southside
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- Ponte Vedra Beach
- Summer Haven st. Augustine FL
- Old A1A Beach
- TIAA Bank Field
- Boneyard Beach
- Kathryn Abbey Hanna Park
- Butler Beach
- Crescent Beach
- Guana Reserve Middle Beach
- Fountain of Youth Archaeological Park
- Amelia Island State Park
- Vilano Beach
- Lightner Museum
- North Beach Guana River Preserve
- Palm Harbor Golf Club
- St. Augustine Alligator Farm Zoological Park
- Matanzas Beach
- Driftwood Beach
- St. Marys Aquatic Center
- Dungeness Beach
- Bent Creek Golf Course
- MalaCompra Park
- Pablo Creek Club
- Amelia Island Lugar Lindo