Guesthouse accommodation & holiday rentals in Southside, Jacksonville

Find and book unique guesthouse accommodation & rentals on Airbnb

Top-rated Guesthouses in Southside, Jacksonville

Guests agree: These guesthouses are highly rated for location, cleanliness and more.

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Guest favourite

Guesthouse in Jacksonville

4.89 out of 5 average rating, 190 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 favourite

Guesthouse in Jacksonville

4.95 out of 5 average rating, 354 reviews

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

Guest favourite

Guesthouse in Jacksonville

4.99 out of 5 average rating, 198 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.

Guest favourite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 129 reviews

The Funk House-A Retreat

If you are requesting to book, make sure that your AIRBNB profile is complete with a current profile pic and a description telling me a little bit about your self. This is a private home, not just a rental, the connections I make through Airbnb are part of the whole experience for me. 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".

Guest favourite

Guesthouse in Jacksonville

4.94 out of 5 average rating, 174 reviews

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.

Guest favourite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 350 reviews

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.

Guest favourite

Guesthouse in Jacksonville

4.9 out of 5 average rating, 227 reviews

Private Bungalow with Pool/55 tv

"The Oasis" is an cozy backyard guest room, detached and separate from the main house, in a beautiful outdoor oasis located in an older neighborhood in the center of Jacksonville, close to I-95, with easy access to everything. 5-7 minutes (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium) and Times Union Center, 20 min to Mayo Clinic (15 miles), 20 min to the beaches (18 miles). NOTE: No animals/pets or children under 12 allowed.

Guest favourite

Guesthouse in Jacksonville

4.95 out of 5 average rating, 149 reviews

Il Rifugio waterfront retreat on the ICW by Mayo!

This peaceful, quiet location on the intercoastal waterway is a perfect place to get away or stay close to Mayo clinic and relax among the bald eagles, owls, dolphins, manatees, etc. Completely private building with raised patio area for you to enjoy. Sleeps up to 4 (1 king size + 1 full size beds) . Close to beaches (4 miles), restaurants, Mayo clinic, 2.5 miles; TPC/ Sawgrass Golf ,10 miles; Saint JohnsTown Center shopping 10 miles; Jacksonville International Airport, 25 min.

Guest favourite

Guesthouse in Jacksonville

4.97 out of 5 average rating, 112 reviews

Modern 1 bedroom dog friendly bungalow

Beautifully renovated retro meets modern bungalow in Jacksonville’s historic Avondale neighborhood. Walking distance to the award winning Restaurant Orsay, The Shoppes of Avondale, Boon Park, and >5 miles to Jacksonville's sports and entertainment complexes. The space is equipped with a nicely appointed kitchen, queen bed, washer, dryer and deck great for relaxing at the end of the day. Our dog friendly space offers double gates to avoid your pup from darting off and dog toy bin.

Guest favourite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 182 reviews

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.

Guest favourite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 254 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 favourite

Guesthouse in Saint Johns

4.97 out of 5 average rating, 209 reviews

Entire Cottage in St Johns, FL with a Water View

We are an easy 35-minute drive to downtown Jacksonville and 45 minutes to historic St. Augustine. Our property is nestled in a serene, tree-lined neighborhood on a canal that flows into the St. Johns River. The cottage is thoroughly cleaned and sanitized before your arrival with a minimum of 24 hours between bookings. The nightly rate INCLUDES St Johns County's bed tax, but Florida sales tax will be added to your booking fees by Airbnb.