Guesthouse vacation rentals in Southside, Jacksonville

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Top-rated guesthouse rentals in Southside, Jacksonville

Guests agree: these guesthouse rentals are highly rated for location, cleanliness, and more.

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Top guest favorite

A two-story detached guest apartment is showcased, featuring a white exterior with black shutters and a welcoming front porch. Two tall palm trees are situated in the yard, which is enclosed by a black wrought-iron fence, offering a spacious green lawn.

Guesthouse in Southwest Jacksonville

4.98 out of 5 average rating, 130 reviews

The Spanish Retreat

This peaceful and central detached guest apartment is located in a friendly neighborhood near the St. John's river, 10 mins from Downtown Jacksonville, and less than a half hour from the beach. Enjoy the privacy of this newly renovated space complete with a queen sized bed, TV, kitchenette, bathroom/shower, closet, and keypad lock for easy access in and out. Lots of restaurants and grocery stores close by! Come relax and unwind in this cozy space perfect for 2! Use caution climbing stairs :)

Top guest favorite

A studio guest suite features a queen bed with decorative pillows and a lightweight blanket. A work desk with a bar stool and a mounted TV are visible against the wall. Light wood flooring complements the soft blue wall, while a woven wall hanging adds texture to the space.

Guesthouse in Southeast Jacksonville

4.92 out of 5 average rating, 288 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.

Top guest favorite

A bright studio suite features a queen-sized bed with a checked blanket and crisp white linens. A retro refrigerator stands nearby, while a sitting area includes a comfortable chair and a small side table. Art decorates the blue-paneled walls, and soft light filters in from a window.

Guesthouse in Avondale

4.94 out of 5 average rating, 139 reviews

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.

Top guest favorite

A bright kitchen features open shelving and stylish cabinetry with a farmhouse sink. A dining table is set for two, showcasing elegant dishware. Soft light is provided by a gold pendant light overhead, highlighting the clean lines and modern design.

Guesthouse in Avondale

4.98 out of 5 average rating, 250 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

A single-story guest house features a warm-toned exterior with a welcoming door. Two red chairs are placed on a small wooden deck, surrounded by lush greenery and flower beds. Pathway stones lead to the entrance, inviting guests to relax in the outdoor space.

Guesthouse in Arlington

4.96 out of 5 average rating, 515 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

Top guest favorite

A spacious studio suite features a large bed with a decorative yellow throw and patterned bedding. A cozy blue accent chair and ottoman are positioned nearby, alongside a small table. The kitchen area is visible in the background, with modern appliances and cabinetry.

Guesthouse in Riverside

4.96 out of 5 average rating, 169 reviews

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.

Top guest favorite

The kitchen features white cabinetry with ample storage and a spacious countertop. Stainless steel appliances, including a double oven and dishwasher, are visible. A window allows natural light to illuminate the workspace, and a small area rug adds a touch of warmth.

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 378 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.

Top guest favorite

A well-appointed studio space features white walls adorned with a light stone accent wall. Shelves display decorative blue and white ceramics. A compact kitchenette is equipped with modern appliances. Bright blue window shutters frame a view of the outside, suggesting a serene atmosphere.

Guesthouse in Riverside

4.97 out of 5 average rating, 190 reviews

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!

Guest favorite

A well-appointed studio apartment features an open layout with a combined kitchen and living area. Warm wood tones mingle with soft white walls, while leather seating surrounds a coffee table. A spacious bed with crisp linens is positioned near large windows, allowing natural light to fill the space.

Guesthouse in Avondale

4.96 out of 5 average rating, 259 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.

Top guest favorite

A gravel pathway winds through a lush outdoor area, framed by towering century-old oak trees. Sunlight filters through the leaves, illuminating the vibrant greenery and creating a serene atmosphere perfect for a peaceful retreat.

Guesthouse in Mandarin

4.98 out of 5 average rating, 123 reviews

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.

Guest favorite

A light-filled living area features a comfortable black sofa adorned with textured cushions. A round dining table with wooden chairs sits nearby. Natural elements are introduced through a potted plant and a woven light fixture, while a piece of artwork adds a touch of color to the wall.

Guesthouse in Springfield

4.99 out of 5 average rating, 135 reviews

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.

Top guest favorite

A detached guesthouse features a covered porch with a small table and two chairs, positioned on a well-manicured lawn. The light-colored exterior is complemented by a series of windows, allowing natural light into the living space.

Guesthouse in Southeast Jacksonville

4.98 out of 5 average rating, 289 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.