Guesthouse vacation rentals in Southside, Jacksonville

A cozy swing chair is situated under a shade structure, surrounded by lush greenery. The view showcases a sparkling pool, sun loungers, and a large blue umbrella providing shade from the sun, creating a tranquil space for relaxation.

4.9 out of 5 average rating, 335 reviews

Private Bungalow with Pool/55” tv

"The Oasis" is an cozy backyard guest room, detached and completely separate from the main house, in a beautiful outdoor oasis nestled in an older but safe neighborhood located in the center of Jacksonville, 1 block from I-95, with easy access to everything. 5-7 min (4-5 miles) from downtown, Convention Center, Veterans Memorial Arena, TIAA Bank Field (Jaguar Stadium), Times Union Center, Mayo Clinic (15 miles), Beaches (18 miles), Airport (18 miles). NOTE: No animals/pets/children under 12.

4.98 out of 5 average rating, 123 reviews

Guesthouse in Mandarin

Pet Friendly Studio w/Tons of 5 Star Reviews

Welcome to the recently renovated Pop's Garage! New pics coming soon! If you've stayed with us before, you'll love the upgrades to our kitchen, the bathroom and the new floors throughout. Plus, we now feature a new, memory-foam King bed and sleeper sofa to accommodate parties of 4. 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

Guesthouse in Southwest Jacksonville

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.

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 :)

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.

4.92 out of 5 average rating, 290 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.

4.94 out of 5 average rating, 141 reviews

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

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.

4.98 out of 5 average rating, 252 reviews

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

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.

4.95 out of 5 average rating, 518 reviews

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

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

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.

4.98 out of 5 average rating, 380 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.

4.96 out of 5 average rating, 260 reviews

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

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 in Springfield

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.

4.99 out of 5 average rating, 136 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.

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.

4.98 out of 5 average rating, 290 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.