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 Jacksonville

4.89 out of 5 average rating, 187 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.

Jul 19 – 26

ﺩ.ﺇ261 per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 340 reviews

Historically charming Studio

Mid Apr 2024, new minsplit AC/Heat, completely painting, new shower tile, new privacy fence, roomier private deck. My studio, is perfect for 2 adults only. It's a great home base while you explore Jacksonville. It's cozy so I keep my rates low, studio which has everything you need for a great stay! You find this wonderful peaceful location is in charming near downtown Jacksonville. The neighborhood was a head of it's time built with parks, shops/restaurants many within walking distance.

Jun 9 – 16

ﺩ.ﺇ265 per night

Guest favorite

Guesthouse in Arlington

4.95 out of 5 average rating, 350 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

Jun 30 – Jul 7

ﺩ.ﺇ330 per night

Guest favorite

Guesthouse in Avondale

4.99 out of 5 average rating, 195 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.

Jul 28 – Aug 4

ﺩ.ﺇ551 per night

Guest favorite

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 350 reviews

Private Apartment With Pool Access

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, laundry, porch, and pool access for our guests only. Complimentary beer, sodas, water and coffee!

Jan 21 – 28

ﺩ.ﺇ465 per night

Guest favorite

Guesthouse in Jacksonville

4.94 out of 5 average rating, 173 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.

Aug 20 – 27

ﺩ.ﺇ444 per night

Guest favorite

Guesthouse in Jacksonville

4.9 out of 5 average rating, 225 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.

Jul 21 – 28

ﺩ.ﺇ273 per night

Guest favorite

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.

Jun 27 – Jul 4

ﺩ.ﺇ539 per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 177 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.

Aug 25 – Sep 1

ﺩ.ﺇ433 per night

Guest favorite

Guesthouse in Jacksonville

4.92 out of 5 average rating, 180 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 :)

Jul 30 – Aug 6

ﺩ.ﺇ307 per night

Guest favorite

Guesthouse in Jacksonville

4.98 out of 5 average rating, 253 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.

May 8 – 15

ﺩ.ﺇ296 per night

Guest favorite

Guesthouse in Saint Johns

4.97 out of 5 average rating, 208 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.

Jun 6 – 13

ﺩ.ﺇ436 per night