Vacation rentals in Southside, Jacksonville

A spacious swimming pool is surrounded by lounge chairs and palm trees, with a sunlit sky in the background. The pool reflects the bright blue sky, while the modern apartment complex stands elegantly behind it.

4.8 out of 5 average rating, 20 reviews

The Sea @ 1319 Near Mayo Clinic

Immerse yourself in comfort at The Sea @1319, a beautifully designed one bedroom/one bath luxury apartment. 🔹Swimming pool with loungers 🔹BBQ Grills 🔹Movie Theater, Clubroom with TVs & Billiards 🔹Private office & Conference Room 🔹Vehicle E-Charging Stations 🔹Free covered parking 🔹Elevator & Wheelchair Accessible 🔹 🔹 BEFORE YOU BOOK 🔹 🔹 The apartment complex requires a background check on all it’s guest. After your reservation is confirmed, we kindly ask that you complete a short form.

Guest suite in Southeast Jacksonville

A private entrance is visible, featuring a light-colored door surrounded by greenery. The pathway leading to the door is made of square stones, bordered by landscaped areas with large leaves and mulch. Two black chairs are placed near the entrance, adding to the welcoming outdoor space.

4.9 out of 5 average rating, 162 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.

Home in Southeast Jacksonville

The entrance displays a black door adorned with a seasonal wreath featuring greenery. A welcome mat with a checkered design is positioned at the foot of the door, enhancing the home’s inviting appearance. The house is surrounded by a neatly maintained lawn.

4.96 out of 5 average rating, 305 reviews

Coastal Lane 3/2 Clean Home in Jacksonville, Wi-fi

Reach out about our multi day discounts for weekdays! This gorgeous 3 bedroom coastal style home is your home away from home! Located in a peaceful and quiet neighborhood with perfect lake views. It's close to shopping, stores, and restaurants. - Easy highway access right off I-95 - 15 minute drive from the Jacksonville Jaguars Stadium (TIAA Bank Field) - 20 minute drive to Jacksonville Beach - 25 minute drive to Jacksonville Airport - Fast Wi-Fi -EV Charge Available for Guests in Garage

Tiny home in Southeast Jacksonville

4.84 out of 5 average rating, 310 reviews

Private yard, all secluded tiny house-your 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!

A dedicated movie theater room is equipped with reclining seats arranged in tiers for optimal viewing. A large projection screen occupies one wall, while soundproofing elements enhance audio quality. Soft lighting fixtures are evenly distributed across the ceiling, providing a comfortable atmosphere.

5 out of 5 average rating, 12 reviews

Red Sails oasis, just minutes from Mayo Clinic

Enjoy a peaceful experience at this centrally-located apartment with all inclusive, resort-like amenities located in Jacksonville, Florida. We are just off of the main highway just minutes from the Mayo Clinic, UNF, and the St. Johns Town Center. * Covered garage parking and elevator access makes it easy to come and go! Take a dip in the beautifully welcoming pool, work out in the fully equipped, 2-story gym, or you can handle your business in the office spaces. There's so much more!

An inviting recreational lounge area features a large pool table positioned near a wall adorned with artistic murals. Bright natural light enters through expansive windows, while comfortable seating and a dining area are visible in the background.

4.91 out of 5 average rating, 35 reviews

Stylish King Bed Southside Jax Pool Gym Mayo UNF

Experience the best of Jacksonville from this luxury 1-bedroom apartment in Southside! You will be just steps from top shopping and dining, with easy access to I-95, downtown, and the stunning beaches of Ponte Vedra. You can start the day with coffee in the modern kitchen before heading out to explore historic St. Augustine or vibrant local hotspots. After a day of adventure, you can unwind in the cozy living area with a smart TV and high-speed Wi-Fi—perfect for a traveler like you!

5 out of 5 average rating, 112 reviews

A welcoming entrance features a beige exterior wall with a neat stairway ascending to the apartment. A potted plant adorns the side, while a doormat with 'Welcome' text creates an inviting atmosphere. Natural light filters in through the open door, highlighting the entryway.

Loft in Avondale

Bright stylish 1bd/1 ba Apt in Historic Avondale.

You'll love this bright stylish second-floor apartment only steps away from the historic Shoppes of Avondale's bars and restaurants. This one bedroom, one bath is so inviting. The open floor plan with windows on all sides provides a bright and airy feel. Amenities such as off-street parking, ensuite washer and dryer, remote workspace, and fully equipped kitchen provide at-home conveniences. Rest and relax in a king-size bed after taking a hot shower or relaxing bath.

Guesthouse in Jacksonville

A cozy outdoor seating area features two woven chairs with accent pillows, paired with a coffee table. The space is paved with square stones, surrounded by lush greenery, creating a sense of privacy and tranquility.

4.96 out of 5 average rating, 102 reviews

The Little House on Jupiter

Good vibes only at La Casita. Stylish, peaceful & private. When it comes to choosing your home away from home- the details matter. Kitchen is equipped with fridge, microwave, air fryer and hot plate. Coffee, hand soap, dish detergent, shampoo and conditioner provided. The bed is full sized. Enclosed side yard. Excellent central location. 10 minutes to the highway, St. John’s Town Center & UNF. 20 minutes to the beaches, downtown & Mayo. No smoking is permitted inside.

Guesthouse in Springfield

An outdoor picnic setup features a low wooden table surrounded by soft cushions. Fresh flowers sit in a vase, while candles and glassware are present. A basket holds drink options. A lush green lawn and soft fabric underlay create a welcoming atmosphere.

5 out of 5 average rating, 123 reviews

Cozy Cottage in Springfield, Downtown Jax

🤍 We can't wait to host you! The Cottage on 4th is located in the eclectic Historic Springfield neighborhood in Jacksonville's urban core. Situated in close proximity to awesome restaurants, coffee shops, breweries, and entertainment venues. Located 1.5 miles or less from TIAA Bank Field, Daily’s Place, Vystar Veterans Memorial Arena, and 121 Financial Ballpark (Jacksonville Jumbo Shrimp stadium). 13 miles from JAX airport and 16 miles from the beach.

4.98 out of 5 average rating, 247 reviews

A compact kitchenette features rustic wooden cabinetry and a stone wall backdrop. A forest mural adds a natural element, while a stainless-steel sink and essential appliances are visible. Utensils are neatly arranged, enhancing the workspace with a warm, inviting ambiance.

Guesthouse in Riverside

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.

Home in Southeast Jacksonville

A clean bathroom countertop is displayed, featuring a circular sink with a chrome faucet. A small potted plant adds a touch of greenery. Mason jar-style soap dispensers are positioned next to a hand towel on a nearby rack, enhancing the space's functionality.

4.98 out of 5 average rating, 42 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!

A spacious community lounge is featured, centered around a dark wood billiards table with colorful pool balls arranged neatly. Exposed wooden beams adorn the high ceiling, while a cozy fireplace is visible in the background along with comfortable seating options.

5 out of 5 average rating, 8 reviews

Heart of Bartram Escape! | No Cleaning Fee

Bright & Modern Apartment in the Heart of Jacksonville! This stylish apartment features a sleek, contemporary design with abundant natural light. Perfect for both work and leisure, it offers a comfortable and inviting space with easy access to everything Jacksonville has to offer.

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Popular amenities for Southside, Jacksonville vacation rentals

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Air conditioning

Other great vacation rentals in Southside, Jacksonville

4.99 out of 5 average rating, 119 reviews

A sandy path leads to the beach, flanked by lush green grasses and small plants. The gentle waves of the ocean are visible in the distance, under a clear blue sky. The scene conveys a sense of tranquility and natural beauty.

Cottage in St. Augustine

Driftwood Cottage by the Sea

LaurenRating, 5 stars4 days ago

This is the 4th year we've stayed with Peter. All of his rentals are beautiful and centrally located to Vilano Beach (steps away) and to downtown St. Augustine. Peter is so quick to respond and helpful with any needs you may have. This year we brought friends and they raved about how excellent the space was as well. My husband's favorite detail is the bread and fruit provided as a welcome gift. We've been coming to vacation in St. Augustine for years and we wouldn't stay anywhere else!

4.9 out of 5 average rating, 146 reviews

An aerial view showcases a spacious swimming pool surrounded by manicured grass and gardens. A covered patio area features colorful loungers and an umbrella, while palm trees provide natural greenery. The layout emphasizes relaxation and outdoor leisure, perfect for family gatherings.

Home in Jacksonville

The Pink Cabana

EllieRating, 5 stars1 week ago

Tannis was the best host ever! She was so very helpful with any and everything!! She made the home so beautiful and it felt like home. My group and I couldn’t have asked for a better home and host. Also, the pool is immaculate!

4.88 out of 5 average rating, 8 reviews

Two hanging chairs with plush cushions are positioned near a heated pool, surrounded by a paved patio. Comfortable outdoor seating with blue cushions is visible in the background, and a large umbrella provides shade. Lush greenery and a clear sky enhance the serene outdoor setting.

Home in Beaches

Family Beach Getaway w/ Pool & Sports Playground

MichelleRating, 5 stars2 weeks ago

Our family thoroughly enjoyed our stay, the backyard was a complete oasis, my daughters and their boyfriends/husbands are in their 20’s and they had as much fun in the backyard as a kid. I had a couple questions while there and host always responded quickly. Great memories made. Thank you

Apartment in St. Augustine

A wooden boardwalk extends toward a sandy beach, framed by tall grasses on either side. The horizon meets a calm ocean under a cloudy sky, featuring a faint rainbow. Soft waves can be seen lapping at the shore.

4.88 out of 5 average rating, 144 reviews

Walk to the Beach 2

CarmelRating, 5 stars1 week ago

Place is exceptionally furnished. Place was kept cool the whole time. No bothersome neighbor. Gorgeous garden.

4.68 out of 5 average rating, 34 reviews

Home in St. Augustine

Cozy Beach House Of Your Dreams

SarahRating, 5 stars2 months ago

I love the charm of this home, chefs kitchen, the house felt spacious, we loved hanging out in the backyard and the front porch, close walk into town but close to the beaches too and lots of local restaurants in walking distance

Townhouse in St. Augustine

4.9 out of 5 average rating, 135 reviews

Paradise Retreat*Vilano Beach*Sand & Ocean Breeze

MarRating, 5 stars2 weeks ago

Given the need for an immediate relocation, Inga was very helpful and her home was just what we needed to enjoy the rest of our vacation. You could tell her home was cleaned very well and we felt right at home.

4.89 out of 5 average rating, 112 reviews

An outdoor deck area is surrounded by wooden railings, featuring a circular arrangement of eight black chairs on a textured rug. A wooden table sits at the center, enhancing the space for gatherings. Lush greenery is visible beyond the deck.

Home in St. Augustine

"The Coastal House" Water Views and a Golf cart!

Lindsay Rating, 5 stars1 month ago

We are so grateful to Tim and Melody for providing a space where our family could be at home for a long weekend. My partner and I are in the process of creating a blended family, so this time together - and the need for it to be peaceful and joyful - was especially important for our young kids. It was everything we could have hoped for and more. We will be back!