
Family-friendly holiday rentals in Southside, Jacksonville
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Top-rated family-friendly rentals in Southside, Jacksonville
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Private Bungalow with Pool/55” tv
"The Oasis" is an cozy backyard guest room, detached and completely separate from the main house, in a beautiful outdoor oasis nestled in an older but safe neighborhood located in the center of Jacksonville, 1 block from I-95, with easy access to everything. 5-7 min (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium), Times Union Center, Mayo Clinic (15 miles), Beaches (18 miles), Airport (18 miles). NOTE: No animals/pets/children under 12.

Studio Suite in Beautiful Central Neighborhood
Studio guest suite with queen bed and kitchenette in beautiful Miramar neighborhood, just 5 minutes from historic San Marco. Close to restaurants, grocery, MD Anderson Cancer Center and Wolfson Children's Hospital. Owners live in main house on site but suite has its own private entrance and parking. You will have access to an outdoor dining space and fenced in backyard. Dogs live on premises but will not interfere, although you may hear barking. Sofa bed available if needed, please inquire.

Elegant 2 King Bed Southside Pool Mayo Clinic UNF
Enjoy the comfort of a spacious, luxury apartment designed just for you. With two large master suites, King beds, and private bathrooms, you’ll have all the space you need to relax and recharge. You can lounge by the resort-style pool, stay active in the state-of-the-art gym, or explore nearby shops and dining at the Town Center. You’re just 15 min from the beach and close to Mayo Clinic. With easy access to I-295, you’ll love how convenient everything is around you in this prime location

Private Apartment
Unique private upstairs apartment near the beautiful Julington Creek very close to St. Johns, under majestic live oak trees offering a quiet and secluded setting, but close enough to everything you need for your next trip to Jacksonville. Short distance to great dining, beaches, shopping, St. Johns and St. Augustine! Guests will enjoy a one bedroom apartment with a fully equipped kitchen. Property access for our guests only. Complimentary beer, sodas, water and coffee! Adults only.

Cozy Retreat By Mayo, Beach, Pet Friendly Backyard
Send me a message for the SUMMER KICKOFF discount Local private host delivering exceptional 5 star experiences nestled in this quiet neighborhood Luxurious beds and blackout curtains offer a relaxing oasis to enjoy your stay. Gather around our large table with family and friends to make memories Pet & family friendly! Sleep 7 guests Convenient to Cruise Terminal, Beach, Mayo, and Shopping/ Dining Private fenced in backyard In Unit Washer/ Dryer DBPR DWE2613890 TDT #1871 LBT #412575

Sunset Retreat | 1BR | 1.5BA | Pool | Gym | Garage
Entire modern, luxurious, and spacious apartment. Stunning lake-front view with gorgeous sunsets. Large king bed and queen sleeper sofa provide a comfortable stay for 4. Whether your stay includes a day of shopping, a trip to golf, going to work, or to unwind at the beautiful Jacksonville beaches, you are never far from your destination. Less than 5 miles to the St. Johns Town Center, 7 miles to the nearest hospital, 11 miles to the beaches, and 6 miles to the nearest golf course.

The Cozy Basement in San Marco
Make yourself at home in this studio-style apartment located in a quiet neighborhood with a kitchenette and full bathroom that features modern updates. Centrally located, less than 5 minutes from historic downtown San Marco with trendy restaurants and shopping, just minutes away from all the shops and nightlife in the village square. Less than 15 minutes to Riverside and downtown Jacksonville including multiple hospitals. Also only 30 minutes from the airport and beaches.

Quiet Private Entrance Backyard Guest Suite
Our small, clean, cozy, guest suite (about 220 sq ft) is located in our fenced backyard. It is detached from our house with a private entrance, in a quiet and safe residential neighborhood. It isn't fancy, but it's a good space for spending a few days while visiting Jax. We offer keyless check-in and free parking is in our driveway. A queen Sealy Posturepedic bed provides ultimate comfort. The suite has a mini-fridge and microwave for simple meals (no full kitchen).

Cozy, private efficiency: Centrally located
Cute, clean efficiency apartment within a larger home. Completely private with separate entry door. Luxury vinyl "wood" flooring, Memory foam mattress. Appliances include dorm fridge/freezer, toaster oven, microwave, burner, coffee pot. Plenty of storage and a large closet. Only 4 miles from the stadium and downtown. 10 miles from Mayo Clinic and 13 to the beach. Centrally located - a great location for concerts, festivals and other events in the Jacksonville area!

Blue Bird Paradise
Welcome to “Bluebird Paradise”. Come visit our bright, beautiful, 400 sq. ft “Guest House”, detached from our home with a porch overlooking our beautiful Florida backyard with pool. The commute is very good; it is located less than 30 minutes from the city, 30 minutes from the beach and 30 minutes from the famous historical St Augustine. Peace and quiet await you. A guesthouse is a detached building that shares the property with the host.

Enchanted Forest: a Magical Luxury Studio
Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.

Hip + Modern Florida Hideaway
Located in historic Murray Hill, our Florida hideaway is a fully renovated hip and stylish private guesthouse brimming with natural light and great vibes! Each room is keenly decorated with high-end modern furniture along with curated vintage art and decor. This space is packed with character and provides all the comforts of home.
Popular amenities for Southside, Jacksonville family-friendly rentals
Family-friendly home rentals with a hot tub

My HOUSE is your HOUSE

Lux Oasis: *Heated Pool, Spa/Hot Tub&Grill Retreat

Private FL Home with Pool, Hot tub & Luxury Master

Yellow Submarine II

Spanish Colonial Design One Bedroom Condominium

Beachy Guest Apartment

Couples clothing optional escape hot tub nude deck

The confetti house - 1 mile from the Mayo clinic!
Family- and pet-friendly home rentals

The Captain's Quarters o|--)

DejaBlu Bungalow (close to Mayo Clinic)

Your Place

Special lakefront retreat

Stylish Bungalow Near Dining,Parks & Entertainment

Spacious 2/1 in historic walkable neighborhood

Charming Apartment in San Marco

Unwind. Cozy Creekside Cottage near Ortega/NAS
Family-friendly home rentals with a pool

Salty Dolphin Cottage with Pool ❤

Cute Pool Cottage in the Historic District

Red Rose Serenity | 1BD Lux King - Southeast Jax

Regency Retreat, 10 minutes from Downtown

Quiet and Serene House with Heated pool near beach

Lake View Escape to The Exchange

Outstanding Southside 2/2 -

Relax in Jax w/ King Bed St Johns Town Center Mayo
Quick stats about holiday rentals that are family-friendly in Southside, Jacksonville
Total rentals
620 properties
Nightly prices starting at
$46 AUD before taxes and fees
Total number of reviews
23K reviews
Pet-friendly rentals
350 properties allow pets
Rentals with a pool
210 properties have a pool
Rentals with dedicated workspaces
390 properties have a dedicated workspace
Destinations to explore
- Smoking-friendly rentals Southside
- Apartment rentals Southside
- Rentals with a hot tub Southside
- Rentals with an EV charger Southside
- Rentals with a fire pit Southside
- Townhouse rentals Southside
- Rentals with a home theatre Southside
- Rentals with pools Southside
- House rentals Southside
- Rentals with breakfast Southside
- Rentals with outdoor seating Southside
- Rentals with lake access Southside
- Rentals with beach access Southside
- Guesthouse rentals Southside
- Pet-friendly rentals Southside
- Private suite rentals Southside
- Waterfront rentals Southside
- Fitness-friendly rentals Southside
- Rentals with a fireplace Southside
- Condo rentals Southside
- Rentals with a washing machine and dryer Southside
- Rentals with a patio Southside
- Family-friendly rentals Jacksonville
- Family-friendly rentals Duval County
- Family-friendly rentals Florida
- Family-friendly rentals United States
- Ponte Vedra Beach
- TIAA Bank Field
- Summer Haven st. Augustine FL
- Old A1A Beach
- San Sebastian Winery
- Vilano Beach
- Boneyard Beach
- Crescent Beach
- Kathryn Abbey Hanna Park
- Lightner Museum
- Fountain of Youth Archaeological Park
- Butler Beach
- Eagle Landing Golf Club
- Pablo Creek Club
- Adventure Landing Jacksonville Beach
- MalaCompra Park
- Matanzas Beach
- Amelia Island State Park
- Stafford Beach
- St. Augustine Alligator Farm Zoological Park
- Ravine Gardens State Park
- Jungle Hut Park
- Old Salt Park
- Bent Creek Golf Course