Guesthouse holiday rentals in Southside, Jacksonville

Cast 'n Anchor in Walkable Avondale

Cast your anchor in a vintage-inspired mother-n-law suite in historic Avondale, a leafy riverside neighborhood near Downtown Jacksonville and 30 minutes to the beach. Conveniently located near I-10 and I-95 and Ortega Marina and within walking distance of the Shoppes of Avondale, the waterfront, public tennis courts and parks. Newly renovated, this studio suite features a comfortable queen-sized bed, a kitchen with a retro refrigerator, flat-screen TV and a bathroom with all the essentials.

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.

Modern Riverside Private Studio

Enjoy a stylish experience at this brand new renovated suite in the heart of Riverside. You will find everything you need in our cozy and private studio. The space includes small kitchen with mini fridge, microwave, toaster, and coffee maker. Within walking distance to many restaurants, breweries, coffee shops and the best bike rental shop in town. We are centrally located to walk to Historic Five Points, King Street, or the St John’s waterfront and a short drive to San Marco & Downtown.

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.

Guesthouse/TPC/Guana Views/Walk Beach/Hot Tub

Discover an enchanting Low Country retreat on the pristine Guana Preserve – one of only 29 National Estuarine Research Reserves. Wake up to breathtaking sunrises over the preserve, walk to the beach half mile away then indulge in the comfort of our studio apartment and private hot tub. Every amenity creates a home away from home ambiance. Bike to the nearby ocean in minutes, where the rhythmic waves serenade you – you can even hear the ocean from the yard!

Pet Friendly Studio w/Tons of 5 Star Reviews

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.

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.

Enchanted Forest: a Magical Luxury Studio

Lost to time, at the end of a long forgotten forest path, where dappled sunlight outline trees, moss, and stone. Enjoy the luxurious richness of satin, velvet, chandeliers and candles. Looking to escape, we’d love to share the path to this hidden destination in Historical Riverside. Equipped for work travel, date night, solo escapes, or longer vacations, this enchanted forest destination is right for you.

Hip + Modern Florida Hideaway

Located in historic Murray Hill, our Florida hideaway is a fully renovated hip and stylish private guesthouse brimming with natural light and great vibes! Each room is keenly decorated with high-end modern furniture along with curated vintage art and decor. This space is packed with character and provides all the comforts of home.