Holiday rentals in Southside, Jacksonville

4.98 out of 5 average rating, 267 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!

4.9 out of 5 average rating, 164 reviews

Guest suite in Lakewood

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.

Guest suite in Jacksonville

4.98 out of 5 average rating, 52 reviews

The Rifugio private studio on waterway near Mayo

Private studio apartment above garage with private entrance. Queen size bed, full bath/shower. Kitchenette area. Close to Mayo clinic (2miles), beach (4 miles), TPC/Sawgrass (10 miles), Saint Johns Town Center shopping/restaurants (8 miles), Jacksonville International Airport (30 miles) Secure, peaceful neighborhood located on the intercoastal waterway. Sit by the pool and enjoy the beautiful view where nature abounds from bald eagles, owls, dolphins, manatees... Come relax at our getaway.

Superhost

4.82 out of 5 average rating, 39 reviews

Resort-Style 1-BR with King Bed – Near Mayo

Welcome to your perfect home base in Jacksonville! Located directly off the main highway, the property offers unmatched convenience and easy access to all the best the city has to offer! Just minutes from the Mayo Clinic, UNF & St. Johns Town Center – ideal for business, school events, dining or shopping. The beach and TIAA Bank Field are only 20 minutes away – enjoy quick access to the coast and local events. Covered garage parking and elevator access make it a breeze to come and go!

Guest house in 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, 4 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!

4.93 out of 5 average rating, 15 reviews

Home in Englewood

The Cozy Woodsy Cottage

Relax at this peaceful, unique, private, centrally-located cozy home that sits on over an acre of property. You can recline on the front porch swing or rocker, or just lounge on the back patio deck. Pool also features a sun deck for lounging or eating with family. Centrally located to all. Shopping, restaurants and attractions only 20 minutes to the beach! The pool on the property. Depth is 3-9ft. We offer a discount when our front house is booked as well. Message for details.

4.9 out of 5 average rating, 21 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.

4.97 out of 5 average rating, 64 reviews

SuperHost Special! 1BR/1BA Luxe Stay in Jax

Our stunning 1BR/1BA apt, is centrally located; whether you're seeking medical expertise at the Mayo Clinic, sun-drenched days on beautiful beaches, or the vibrant retail, dining or nightlife of St. Johns Town Center, our luxe unit is at the center of it all. We've curated our home with your comfort and lifestyle in mind, enjoy a private/quiet atmosphere with modern amenities, luxe furnishing and bedding, fully equipped kitchen, dining Area and dedicated workspace with wifi.

5 out of 5 average rating, 106 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.