Holiday rentals in Southside, Jacksonville

4.98 out of 5 average rating, 266 reviews

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!

4.87 out of 5 average rating, 61 reviews

Lux King Bed Stunning View Pool Mayo Clinic Beach

Start your Jacksonville stay with comfort and style! This modern 1-bedroom apartment in a prime location puts you just 10 minutes from Mayo Clinic and 15 minutes from the beach. You’ll enjoy a fully equipped kitchen, a cozy bedroom, and a stunning view that will elevate your experience. Whether you’re here for treatment, work, or a beach escape, you’ll find everything you need for a relaxing, stress-free stay. Enjoy the comfort, convenience this apartment offers for a seamless long or short stay

Superhost

Tiny home in Southeast Jacksonville

4.84 out of 5 average rating, 314 reviews

Entire place with private yard, tiny house oasis!

Come play at the beach! 24’ tiny house on a private fenced yard with gas grill, tropical outdoor area for relaxing. Lofted sleeping space, with shower and toilet make this the perfect weekend getaway or the escape from work meetings. Close to Mayo Clinic, Downtown , & Florida Beaches all a 15 minute drive! Or enjoy Orlando and natural springs with manatees couple hours away. St Johns town outdoor mall is a 5 minute drive and has countless food and shopping options! Truly a unique experience!

Guest house in Southeast Jacksonville

4.98 out of 5 average rating, 374 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.

Superhost

5 out of 5 average rating, 3 reviews

Serenity Retreat| 1BD Lux King in Southeast Jax

Welcome to your own personal retreat! Let go of the weight of daily life and step into a world of tranquility, where stress fades and serenity takes over. Experience the calming ambiance of a spa like retreat, relaxing music, and soft lighting, all designed to create profound peace. This is more than a stay—it’s a curated experience designed to recharge your spirit, awaken your clarity, and inspire your dreams. Let go, unwind, and manifest your best self. Your escape begins here!

4.9 out of 5 average rating, 20 reviews

Blue Skies 1 Bedroom 1 Bath Apt

Stylish, centrally-located w/resort-like amenities. Just off of the main highwway minutes from the Mayo Clinic, UNF, & St. Johns Town Center. • pool & loungers • grills • club room /TVs & billiards • private offices & conf room • vehicle E charging stations • covered parking/elevator & wheelchair accessible ** upon confirmation, you will be required to complete a short form and to submit a copy of your ID. The complex requires this to secure the safety of residents and guests.

4.95 out of 5 average rating, 227 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.

5 out of 5 average rating, 105 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.

Apartment in Southeast Jacksonville

4.95 out of 5 average rating, 127 reviews

Charming & Cozy 3-bedroom Condo 15mn to the Beach

Your family will be close to everything when you stay at this centrally-located place. Charming and cozy condo in a family friendly neighborhood located in the heart of Jacksonville, 10min away from St. john’s Town center, Tinsel Town and a number of restaurants . 15 mns to TIAA Stadium, 20mn to Jacksonville Beaches, Downtown, and Mayo clinic. 20 min to mayport Naval Base. Great location for a traveling professionals looking for a temporary or long term housing.

Home in Southeast Jacksonville

4.91 out of 5 average rating, 103 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.

Home in Southeast Jacksonville

4.98 out of 5 average rating, 46 reviews

Near Jaguars Stadium| Near Towncenter |Mayo Clinic

Unwind in this stylish, tranquil retreat. Enjoy the perfect blend of comfort and convenience in our 3-bedroom, 2.5-bath home, steps from Starbucks. Relax in the peaceful backyard by the fire pit or use the garage for luggage (no car parking). Just 1-2 minutes from I-95, 10 minutes from the town center, and 20 minutes from the beach, you’re surrounded by dining, shopping, and more—your perfect getaway hub!