
Guesthouse vacation rentals in Southside, Jacksonville
Find and book unique guesthouse rentals on Airbnb
Top-rated guesthouse rentals in Southside, Jacksonville
Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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.
Popular amenities for Southside, Jacksonville guesthouse rentals
Family-friendly guest house rentals

Beach Bliss Hideaway: 1bd Gem!

Townville home

The Garden Casita in St. Augustine Florida

Captain's Quarters Tiny House

little dream

Loft in the trees

Serene Getaway at the White House

Luxury Cottage with River Access
Guest house rentals with a patio

The Little House

Tropical guest house a few blocks from the beach

Adorable 2 Bedroom Cottage

Comfortable and Gently Disney.

The Moody Loft (Murray Hill)

Lovely Guesthouse in the Up-and-Coming Springfield

Private Riverfront Guest House 15 min to downtown

Oasis/King bed/Mayo/UNF/beaches
Guest house rentals with a washer and dryer

Charming Pet-Friendly Guesthouse in Avondale

La Casita Chiquita Near Events & Entertainment!

Downtown Jacksonville Historic District

Henry’s Pad

The Funk House-A Retreat

Graceful Southern Guesthouse + Outdoor Living Area

Treetop Carriage Apartment

Large 1 bedroom Cottage with full kitchen
Quick stats about guesthouse rentals in Southside, Jacksonville
Total rentals
20 properties
Nightly prices starting at
€ 43 before taxes and fees
Total number of reviews
2.9K reviews
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
10 properties have a dedicated workspace
Wifi availability
20 properties include access to wifi
Destinations to explore
- Fitness-friendly rentals Southside
- Waterfront rentals Southside
- Rentals with outdoor seating Southside
- Rentals with pools Southside
- Rentals with breakfast Southside
- Private suite rentals Southside
- Family-friendly rentals Southside
- Rentals with a fire pit Southside
- Rentals with an EV charger Southside
- Rentals with beach access Southside
- Rentals with lake access Southside
- House rentals Southside
- Rentals with a home theater Southside
- Rentals with a hot tub Southside
- Townhouse rentals Southside
- Rentals with a patio Southside
- Rentals with a fireplace Southside
- Apartment rentals Southside
- Pet-friendly rentals Southside
- Smoking-friendly rentals Southside
- Condo rentals Southside
- Rentals with a washer and dryer Southside
- Guesthouse rentals Jacksonville
- Guesthouse rentals Duval County
- Guesthouse rentals Florida
- Guesthouse rentals United States
- Ponte Vedra Beach
- TIAA Bank Field
- Summer Haven st. Augustine FL
- Old A1A Beach
- San Sebastian Winery
- Vilano Beach
- Boneyard Beach
- Crescent Beach
- Kathryn Abbey Hanna Park
- Lightner Museum
- Fountain of Youth Archaeological Park
- Butler Beach
- Pablo Creek Club
- Eagle Landing Golf Club
- Adventure Landing Jacksonville Beach
- MalaCompra Park
- Matanzas Beach
- Amelia Island State Park
- Stafford Beach
- St. Augustine Alligator Farm Zoological Park
- Ravine Gardens State Park
- Jungle Hut Park
- Old Salt Park
- Bent Creek Golf Course