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.

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Guest favorite

Guesthouse in Southeast Jacksonville

4.91 out of 5 average rating, 228 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 favorite

Guesthouse in Avondale

4.99 out of 5 average rating, 222 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 favorite

Guesthouse in Riverside

4.98 out of 5 average rating, 136 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 favorite

Guesthouse in Arlington

4.96 out of 5 average rating, 411 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 favorite

Guesthouse in Murray Hill

4.92 out of 5 average rating, 211 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 favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 362 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 favorite

Guesthouse in Southeast Jacksonville

4.96 out of 5 average rating, 171 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 favorite

Guesthouse in Avondale

4.95 out of 5 average rating, 615 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.

Guest favorite

Guesthouse in Avondale

4.97 out of 5 average rating, 216 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 favorite

Guesthouse in Mandarin

4.98 out of 5 average rating, 103 reviews

Charming, Pet Friendly Retreat in Heart of NE FL

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.

Guest favorite

Guesthouse in Murray Hill

4.92 out of 5 average rating, 251 reviews

The Moody Loft (Murray Hill)

Kick back and relax in this calm, stylish space. Dimmable lights for your preference. It's within minutes of Jacksonville's best night life. Walk to Murray Hill's bars and restaurants. Less than 5 minute drive to Riverside's Historic 5 Points. Less than 10 minutes from downtown and 25 minutes from beaches. There's a small fence separating my main house, enjoy sitting outside. My Newfies might peek over the fence every now and then to say hello :)

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 268 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.