Guesthouse vacation rentals in Southside, Jacksonville

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Top-rated guesthouse rentals in Southside, Jacksonville

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

The guesthouse exterior features a welcoming front porch with two chairs and a small side table, surrounded by colorful plants. Sheer curtains adorn the entrance, and bicycles are parked nearby, creating an inviting space for relaxation and leisure.

Guesthouse in Southwest Jacksonville

4.92 out of 5 average rating, 135 reviews

{Owl's Nest} Avondale Guesthouse *No Cleaning Fee!

Get cozy in this Historic Avondale guesthouse with it's modern, boho accents. Cottage boasts a bright living area & work space, a place for mixing cocktails, & a private front porch perfect for reading a book or soaking up the sunshine. Take a cruise on our bikes through Avondale or down to the river to enjoy a Florida sunset. Located just minutes from Downtown Jax & Sports Complexes, Naval Air Station, Area hospitals, Florida State College @ Jax, Area Beaches, St. John's River, I-95 & I-10.

Top guest favorite

A vibrant street view captures a historic theater, where the marquee displays upcoming shows. Flanking the theater, local businesses are visible, with a coffee shop on one side and a boutique on the other. The scene is framed by partly cloudy blue skies.

Guesthouse in Avondale

4.99 out of 5 average rating, 103 reviews

Charming Pet-Friendly Guesthouse in Avondale

Charming guesthouse centrally located in Jacksonville's historical Avondale area. The guesthouse has been recently renovated with queen bed, sofa bed, well equipped kitchen, and full size bathroom with tub/shower, washer and dryer on property. Super dog friendly. Walk to restaurants Iguana on Park & Orsay, convenient store, and laundry facilities, and Boone Park. The Shoppes of Avondale 0.6mi, St. Vincent's Med Ctr 1.4mi, Sports Complex 4.8mi, Vystar Memorial Area 4.4mi, and Metro Park 4.8mi.

Guest favorite

A serene beach scene captures a stretch of sand bordered by gentle waves and a dramatic sky marked by wispy clouds. The coastline leads to a distant house, situated against the backdrop of the setting sun, creating a tranquil and inviting atmosphere.

Guesthouse in Beaches

4.88 out of 5 average rating, 139 reviews

Beach cottage beauty

Enter the cottage — new, yet built to look like it's been in the neighborhood of Old Ponte Vedra Beach for 100 years — you'll feel a deep calm while experiencing tasteful, elegant, and comfortable beach charm. Perfect for a couple or girls getaway, the space gives the feel of a cozy, quiet treehouse in a pristine, quiet neighborhood street. Amongst the palm trees and ocean air, the cottage is perfect for restoration, creating and to soak up the sun — all within 5 minutes walk to the ocean.

Top guest favorite

Guesthouse in Avondale

4.98 out of 5 average rating, 241 reviews

Luxury Avondale Guest House, Walk to Shops

Featured in the Jacksonville Home Magazine! The Luxury Avondale Guest House is in the exquisite historic neighborhood of Avondale. Ten minutes from downtown sports & entertainment complexes, and several major health care facilities, St. Vincent's Hospital, Baptist Medical Center and the world renowned MD Anderson Cancer Center. Three short blocks to “The Shoppes of Avondale,” with an outstanding array of restaurants and venues to enjoy a streetside café-style meal, cocktail and desserts.

Top guest favorite

A modern bathroom features a sleek black and white color scheme. A glass shower enclosure is seen alongside a compact vanity with a dark countertop. Soft lighting is provided by four wall-mounted fixtures above a large mirror, and a towel is draped on a rack.

Guesthouse in Southwest Jacksonville

4.96 out of 5 average rating, 140 reviews

Private, Modern And Cozy Guesthouse

Kick back and relax in this calm, stylish space. Enjoy the privacy of this newly renovated unit complete with a queen-sized bed, and a small living room with a sleeper sofa, so the place can comfortably accommodate up to three. Also included, a 50-inch smart TV, kitchenette, bathroom/shower, closet, and keypad lock for easy access in and out. Please note that we have an exterior security camera on the front to enhance your security and safety. Conveniently situated 1 mile off Highway 295.

Top guest favorite

Aerial view of the property reveals a well-maintained lawn surrounded by tall palm trees. A pathway leads to a private guesthouse, with a red roof and white doors. A tranquil pond with stones adds a natural element to the landscaped garden.

Guesthouse in Beaches

5 out of 5 average rating, 203 reviews

Tropical guest house a few blocks from the beach

Take it easy at this unique and tranquil getaway. Private modern quest house located on lush tropical grounds behind main house. Includes: loft bedroom, full bath, kitchenette, wifi, air conditioning, private patio, and outdoor shower. Property is gated with parking. Walking distance to beach, bars, shops and restaurants. Hammock, volley ball, firepit, BBQ and bikes available upon request. Pets welcome. Fishing pier, boating, kayaking and golf options within a short distance.

Guest favorite

The open living space features a comfortable sofa facing a mounted flat screen TV. A dining table set for two is located nearby, and a spiral staircase leads to the second floor. Natural light enters through large garage-style doors and a side entrance.

Guesthouse in Avondale

4.95 out of 5 average rating, 637 reviews

The Captain's Quarters o|--)

This two story loft garage is detached and is set in the back of the property 45 feet from the main house. The first floor has the kitchen and living space, then walk up the spiral staircase to the bedroom with cathedral ceiling with track lights and ensuite bathroom. I love dogs and allow them with permission first. No pets without prior approval (pet fee is min $50 per stay or $10 per day which ever is greater) My location is a short walk to Starbucks and other restaurants.

Top guest favorite

An outdoor shared backyard area is presented, featuring a large wooden dining table surrounded by chairs. Lounge seating is arranged on gravel, with string lights overhead and various potted plants enhancing the serene atmosphere.

Guesthouse in Riverside

4.97 out of 5 average rating, 173 reviews

Santorini A Mediterranean Studio Escape…Riverside

Escape to a tranquil Greek villa in the heart of Riverside, Jacksonville. Inspired by the cliff top town of Ioa on the island of Santorini, you will experience the allure of the Aegean Islands as you step into this whitewashed windswept studio. Immerse yourself in bleached white rock, stucco, and cobalt blue accents. Escape if you’d like or walk to local eateries and entertainment. Regardless, enjoy the magic of a Grecian villa hidden in the middle of Riverside Jacksonville!

Top guest favorite

The kitchen features modern cabinetry and stainless steel appliances. A round table with wooden chairs is positioned in the center, adorned with a vase of fresh flowers. Natural light is let in through a window, complemented by soft window treatments.

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.

Guest favorite

A vibrant kitchen showcases bold orange walls and black cabinets adorned with decorative accents. A stove, microwave, and sink are visible, with a kettle and small appliances on the counter. Red lanterns hang above, contributing to the eclectic atmosphere.

Guesthouse in Riverside

4.95 out of 5 average rating, 150 reviews

The Funk House-A Retreat

If you are requesting to book, make sure that you have a complete AIRBNB profile, a current profile pic and phone number. Your request should include, what brings you to the Jacksonville area, along with an approximate time of arrival. The Retreat is separate from the main house (The Funk House) it is located in the back, on the top floor garage apartment. It has been completely renovated and furnished into a comfortable place to "Retreat".

Top guest favorite

A tranquil swimming pool is set against a backdrop of trees and a gentle sunlight. The pool features a smooth, light-colored deck with decorative pots at the edge, enhancing the peaceful ambiance. Comfortable chairs are visible nearby, ideal for relaxation.

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 282 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.

Guest favorite

The exterior of the guesthouse showcases a charming A-frame design, featuring a white façade and large windows that provide ample natural light. A landscaped area surrounds the structure, and a small dog stands nearby, adding to the welcoming atmosphere of the setting.

Guesthouse in Murray Hill

4.98 out of 5 average rating, 126 reviews

MidCentury Guesthouse-NO Cleaning Fee+Restaurants

Our Mid Century inspired guesthouse is truly unique and just steps away from Murray Hill Four Corners park. Enjoy modern amenities with a classic flare. Easy entry and exit with off street parking for 2 vehicles and keypad entry. Conveniently located minutes from popular attractions on Edgewood in Murray Hill, Riverside, the Shoppes of Avondale, 5 points, downtown, and hospitals. Please note we discontinued use of the electric gate.