Guesthouse holiday rentals in Southside, Jacksonville

The Spanish Retreat

This peaceful and central detached guest apartment is located in a friendly neighborhood near the St. John's river, 10 mins from Downtown Jacksonville, and less than a half hour from the beach. Enjoy the privacy of this newly renovated space complete with a queen sized bed, TV, kitchenette, bathroom/shower, closet, and keypad lock for easy access in and out. Lots of restaurants and grocery stores close by! Come relax and unwind in this cozy space perfect for 2! Use caution climbing stairs :)

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

Large 1 bedroom Cottage with full kitchen

This is a full size one bedroom house with full brand new kitchen and private entrance. The entire place was renovated late 2021. A luxurious king size bed awaits you and a twin sized sofa bed for one adult or two kids. The kitchen has a full sized brand new oven, stove, microwave, dishwasher and fridge and is stocked with utensils etc so you can easily make full meals or stay for an extended time. There's one free off-street parking spot available and plentiful free street parking.

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.

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 located in an older neighborhood 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.

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.

Pet Friendly Hub for Summer FUN!

Welcome to Pop's Garage! Nestled in Jacksonville's vibrant Mandarin area, this beautifully renovated property blends modern comforts and rustic charm. As the perfect Northeast Florida retreat, Pop's Garage offers a cozy and convenient stay. 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.

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.