Family-friendly vacation rentals in Southside, Jacksonville

4.98 out of 5 average rating, 273 reviews

A spacious living area is presented with a light-colored sofa and a matching ottoman, complemented by a deep blue armchair. The room features a decorative round mirror, hardwood flooring, and an archway leading to a dining space with a table for six, illuminated by natural light.

Home in San Marco

Luxurious Craftsman in Historic San Marco

Never Drive Again! Immaculately renovated San Marco Bungalow, just a minute from excellent restaurants, retail, entertainment, hospitals & easy transit (via San Marco's FREE Beachside Buggy App) to everything else. Features include an inviting front porch, interior foyer, charming living room w/gas fireplace, new kitchen w/SS and granite, indoor laundry, historic architectural features, and private backyard w/ sitting area, fire pit, games & BBQ! Incredible location with unmatched walkability!

Guest suite in Southeast Jacksonville

A bright sleeping area is presented, featuring a spacious bed with white linens and decorative pillows. A chair is positioned nearby, alongside a lamp and a mirrored dresser. Natural light filters through large windows, adorned with blinds, with greenery visible outside.

4.9 out of 5 average rating, 170 reviews

Cute private guest suite in charming neighborhood

Whether you are visiting for work, vacation or planning a local getaway, our guest suite is thoughtfully set up to provide what you need for your stay. In a friendly, residential area we are located on quiet street, where large trees and greenery create a natural canopy, providing for a cool and cozy side yard for you to enjoy during your stay. Centrally located to many of Jacksonvilles popular attractions so you can enjoy peace and quiet while restaurants and shops are within walking distance.

4.95 out of 5 average rating, 131 reviews

Home in Jacksonville

Special lakefront retreat

Your family will be close to everything when you stay at this centrally-located place. Minutes to major shopping and restaurants and just 15 minutes to Jacksonville beach. Only 10 min to TIAA Bank Field to see the Jaguars or enjoy your favorite events. Home features a scenic backyard with lake views. You can sit on the fishing deck or relax on the dining family deck . If you like to kayak, go for it. Then come back to enjoy a nice evening with family or friends around the firepit.

A clear swimming pool is depicted, showcasing calm water with scattered floating toys. Sunlight reflects off the surface, creating a serene atmosphere. Surrounding the pool are several black lounge chairs, providing space for relaxation.

4.86 out of 5 average rating, 214 reviews

Private FL Home with Pool, Hot tub & Luxury Master

This is a lovely family home in the Mandarin area of Jacksonville which has undergone many renovations and upgrades. The master boasts its own, ensuite, tv, fireplace and sitting area, as well as a private entrance from the pool and hot tub area. The house itself has newer furnishings, flooring, modern decor, a large fenced in backyard, pickle ball court and firepit. Located in a safe South East Suburb of Jacksonville, not far from shopping, beaches and many other Florida attractions.

Guesthouse in Southeast Jacksonville

The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.

4.98 out of 5 average rating, 378 reviews

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.

4.97 out of 5 average rating, 277 reviews

A welcoming living area features comfortable seating arrangements, including a large green sofa and two gray armchairs. Natural light fills the space through large windows, and a flat-screen TV stands on a small table. A textured rug adds warmth to the hardwood floor.

Home in Jacksonville

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

Apartment in Southeast Jacksonville

A modern kitchen with granite countertops and stainless steel appliances opens to a spacious living area. Large windows provide natural light and a view of the outdoors. A comfortable seating area with blue furniture and a dedicated workspace can be seen, enhancing the inviting atmosphere.

4.95 out of 5 average rating, 230 reviews

Top floor modern getaway w/resort amenities!

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.

Apartment in Southeast Jacksonville

The studio features a spacious bed with a light-colored blanket and decorative pillows. A cozy sofa sits in the corner, accompanied by a coffee table. Green plants are placed throughout, and ample natural light enters through a window, complemented by thoughtful décor on the walls.

5 out of 5 average rating, 122 reviews

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.

A dining area features a wooden table surrounded by six chairs. Natural light enters through multiple windows, illuminating the space. A chandelier hangs from the ceiling, complementing the wall paneling and enhancing the room's cozy ambiance.

4.97 out of 5 average rating, 192 reviews

A Secluded Modern and Cozy Home Near Downtown

Have a family getaway, girls weekend, or just hanging with your friends, not a better location to enjoy downtown Jacksonville and the beautiful San Marco neighborhood than at this peaceful, secluded peace of paradise. Minutes to downtown and only 100 yards from the beautiful St. John's River, Spacious modernized home with 70 inch tv's in living room and family room, with 43 inch tv's in all bedrooms. High speed internet, YouTube TV with NFL Sunday Ticket and RedZone!

Guesthouse in Southeast Jacksonville

A detached guesthouse features a covered porch with a small table and two chairs, positioned on a well-manicured lawn. The light-colored exterior is complemented by a series of windows, allowing natural light into the living space.

4.98 out of 5 average rating, 289 reviews

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.

A modern kitchen is equipped with sleek white cabinets and a spacious countertop. A stainless steel refrigerator and high-end appliances are visible, along with an induction cooktop seamlessly integrated into the surface. Soft lighting illuminates the area, creating a functional cooking space.

4.91 out of 5 average rating, 104 reviews

Cozy house in a heart of Mandarin

Come and relax in the cool walls of a house located on a quiet street in the heart of the Mandarin. You will see 3 spacious bedrooms (master bedroom is king size, others are queen sizes) 2 bathrooms, fully equipped kitchen, new furniture. Everything else comes with a place near the fireplace, where you can gather. Clean and new house with amenities. Jacksonville Beach in 25 min. We allowed 2 pets. We charge $100 fee for pet.

A spacious living area features a modern sectional sofa positioned around a coffee table. Large windows allow natural light to fill the room, highlighting a stone fireplace. A flat-screen TV is mounted on the wall, complemented by decorative artwork on either side.