Vacation rentals in Southside, Jacksonville

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Top-rated vacation rentals in Southside, Jacksonville

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Guest favorite

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.

Guest suite in Southeast Jacksonville

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.

Top guest favorite

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.

Home in Southeast Jacksonville

4.96 out of 5 average rating, 302 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

Top guest favorite

A black wrought iron gate stands closed, providing access to a paved path leading to the guest suite. White siding is visible on the adjoining building, while nearby greenery contributes to a natural setting. The scene is set under a clear blue sky.

Guesthouse in Southeast Jacksonville

4.92 out of 5 average rating, 271 reviews

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.

Guest favorite

A dedicated movie theater room is equipped with a large screen and multiple comfortable recliner seats, arranged for optimal viewing. The walls feature a dark color scheme, enhancing the cinematic experience, while a low platform adds to the tiered seating layout.

Apartment in Southeast Jacksonville

4.95 out of 5 average rating, 223 reviews

Top floor modern getaway w/resort amenities!

New build! 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.

Guest favorite

A spacious living area is featured, showcasing a light-colored sectional sofa paired with two upholstered armchairs. A modern coffee table sits in the center, surrounded by natural light from large windows. Soft blue walls complement the neutral tones of the furnishings.

Condo in Southeast Jacksonville

5 out of 5 average rating, 9 reviews

Town Center Hideaway

Welcome to our cozy retreat in the heart of Jacksonville. This stylish and modern condo is nestled in an urban village interlaced with boutique retail shops, popular eateries, and attractions, with easy access to major highways for exploring the city. Unwind in our well appointed living space, complete with a fully equipped kitchen, a spacious bedroom, and luxury amenities. Whether you’re here for business or leisure, this condo provides the perfect base for your Jacksonville adventures.

Top guest favorite

An indoor lounge area features a billiards table at the center, surrounded by minimalist furniture. Large windows allow natural light to fill the space, revealing views of a swimming pool and tropical landscaping just outside.

Apartment in Southeast Jacksonville

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!

Superhost

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.

Apartment in Southeast Jacksonville

4.91 out of 5 average rating, 34 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!

Top guest favorite

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

5 out of 5 average rating, 110 reviews

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.

Top guest favorite

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.

Guesthouse in Jacksonville

4.96 out of 5 average rating, 101 reviews

La Casita 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.

Guest favorite

A softly illuminated walkway is visible, guiding towards a fence and greenery. The path is bordered by fresh landscaping, with subtle lighting that enhances the serene outdoor atmosphere during the evening.

Guest suite in Southwest Jacksonville

4.89 out of 5 average rating, 246 reviews

Stylish Private Master Suite With Private Entrance

PLEASE READ BEFORE BOOKING: *This suite is apart of a duplex. It is attached to another Airbnb, however this Airbnb space is NOT shared with others. You will have this private place to yourself and just your guest will be in it with you. We all stayed at places while on vacation in cities that are far from entertainment at least once. The Riverside area is full of different restaurants, attractions, and entertainment options that will keep you full & entertained.

Guest favorite

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.

Guesthouse in Springfield

5 out of 5 average rating, 122 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.

Top guest favorite

A bird is observed emerging from a circular opening in a pink birdhouse. Floral decorations in blue and green surrounding the entrance add a charming touch. The bird's speckled feathers are visible, highlighting its natural camouflaging patterns against the wooden structure.

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 285 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.