Guesthouse vacation rentals in Southside, Jacksonville

Private Bungalow with Pool/55” tv

"The Oasis" is an cozy backyard guest room, detached and completely separate from the main house, in a beautiful outdoor oasis nestled in an older but safe neighborhood located in the center of Jacksonville, 1 block from I-95, with easy access to everything. 5-7 min (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium), Times Union Center, Mayo Clinic (15 miles), Beaches (18 miles), Airport (18 miles). NOTE: No animals/pets/children under 12.

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.

Jax Backyard Bungalow

Rent this pet friendly guest house in our quiet well-groomed backyard. Studio comes with queen-size bed, couch, closet, mini fridge, Keurig, microwave, table & chairs. Enjoy DirecTV & dedicated WiFi router. Savor a peaceful cup of coffee or evening cocktail on the attached wood deck. Well behaved pets are encouraged to run free in the fully fenced in yard. Our black lab would love the company! Get to TIAA Bank Field in less than 5 mins or the beach in about 25 mins. Must be 25 to book

The Treehouse - Murray Hill

Enjoy all the comforts of home in this remodeled guesthouse. Features keyless entry for easy self check-in, mini kitchenette with one-burner induction cooktop, microwave, Keurig coffee maker, utensils, and cookware. Free Wi-Fi, 43" Smart TV, linens, full-size bed in the sleeping area with a private deck off the back sitting high amongst the trees. Parking on well-lit quiet street with security camera coverage in select areas. No indoor smoking/vaping allowed. DM for questions/exceptions!

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.

Jax Coastal Cottage

Charming private cottage in historic Avondale neighborhood of Jacksonville with no cleaning fees! Just 10-minutes to downtown Jacksonville's riverwalk and sports stadiums. Plus, the cottage is walkable to local neighborhood parks, ice cream shops, coffee shops, restaurants, and pubs. Complimentary beach chairs, umbrella and beach towels provided! Great amenities provided plus an in-unit washer/dryer and a cute outdoor space to call home while visiting beautiful Jacksonville!

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!

Pet Friendly Studio w/Tons of 5 Star Reviews

Welcome to the newly renovated Pop's Garage! If you've stayed with us before, you'll love the upgrades to our kitchen, the bathroom and the new floors throughout. Plus, we now feature a new, memory-foam King bed and sleeper sofa to accommodate parties of 4. The pet-friendly space includes a private and secure fenced-in area, allowing your canine to stretch out and explore. Discover the perfect balance of comfort and convenience at this one-of-a-kind vacation rental

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.

Avondale Studio

Located in Avondale, Jacksonvilles historic district, this Garage Studio offers everything one needs for a getaway or a business trip. Walking distance to the Shoppes of Avondale. There are multiple restaurants/bars/outdoor cafe dining all within walking distance in either direction. The 2nd story garage apartment offers a balcony with views into Boone Park. Fully renovated in 2021 offering a full kitchen and bathroom. You have a private parking space as well.

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.

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.