Guesthouse holiday rentals in Southside, Jacksonville

Charming Pet-Friendly Guesthouse in Avondale

Charming guesthouse centrally located in Jacksonville's historical Avondale area. The guesthouse has been recently renovated with queen bed, sofa bed, well equipped kitchen, and full size bathroom with tub/shower, washer and dryer on property. Super dog friendly. Walk to restaurants Iguana on Park & Orsay, convenient store, and laundry facilities, and Boone Park. The Shoppes of Avondale 0.6mi, St. Vincent's Med Ctr 1.4mi, Sports Complex 4.8mi, Vystar Memorial Area 4.4mi, and Metro Park 4.8mi.

Beach cottage beauty

Enter the cottage — new, yet built to look like it's been in the neighborhood of Old Ponte Vedra Beach for 100 years — you'll feel a deep calm while experiencing tasteful, elegant, and comfortable beach charm. Perfect for a couple or girls getaway, the space gives the feel of a cozy, quiet treehouse in a pristine, quiet neighborhood street. Amongst the palm trees and ocean air, the cottage is perfect for restoration, creating and to soak up the sun — all within 5 minutes walk to the ocean.

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.

Tropical guest house a few blocks from the beach

Take it easy at this unique and tranquil getaway. Private modern quest house located on lush tropical grounds behind main house. Includes: loft bedroom, full bath, kitchenette, wifi, air conditioning, private patio, and outdoor shower. Property is gated with parking. Walking distance to beach, bars, shops and restaurants. Hammock, volley ball, firepit, BBQ and bikes available upon request. Pets welcome. Fishing pier, boating, kayaking and golf options within a short distance.

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!

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.

MidCentury Guesthouse-NO Cleaning Fee+Restaurants

Our Mid Century inspired guesthouse is truly unique and just steps away from Murray Hill Four Corners park. Enjoy modern amenities with a classic flare. Easy entry and exit with off street parking for 2 vehicles and keypad entry. Conveniently located minutes from popular attractions on Edgewood in Murray Hill, Riverside, the Shoppes of Avondale, 5 points, downtown, and hospitals. Please note we discontinued use of the electric gate.

Cozy Cottage

Centrally positioned amid Jacksonville, St. Augustine, and the beaches, our guesthouse provides easy access to local shopping and amenities. Located near the scenic St. Johns River, guests can enjoy fishing and water activities.