Smoking-friendly holiday rentals in Southside, Jacksonville

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.

Cozy Private Tiny Guest House

This gorgeous and elegant Tiny style room with a great Westside location. Very private, warm and Comfortable. You can have some privacy to work or just relax after a long day. Most of our guests are coming from all over the country for special events, or simply for a getaway as a couple. Brand new furniture’s, smart TV, WIFI. Electronic lock door and security measures, safety and friendly neighborhood. You'll love this unique and romantic escape. Kick back and relax in this calm, stylish space.

Private oasis, heated pool, exceeds expectations

Private retreat on 2 acres of gated land, just 20 minutes to historic downtown St. Augustine and 25 minutes to the beach. This fenced property offers a perfect blend of relaxation, fun, and comfort. Enjoy your private pool, or let the kids enjoy their own space in the pool house, featuring TV, games, and a cozy hangout area. Start your day with fresh eggs from our happy hens- an experience that feels both farm-fresh and uniquely memorable. This home is designed to make your stay unforgettable.

KING BED/PVT Balcony/Fast Wifi/65 inch Tv/Pool+Gym

want you! Tell me what I can do to be your host." Click Profile Pic over 200 ⭐⭐⭐⭐⭐ reviews 🐕 INBOX FOR DETAILS FOR PET FEE! 🚪 Early check in available inbox for details 🚪Late checkout available 🛏️Sleep in comfort $700 king mattress designed for a restful night’s sleep. 🛏️King Bed 📶Super-Fast Wi-Fi 🏋️‍♂️24hr Gym 📺65" Mounted TV in Living Room 50" Bedroom 💦 Natural Spring Saltwater Pool 🌄 Relax on your private balcony with a lake front view 🛏️🧳Extra air bed for guests

Private home @ Pristine neighborhood

Private home with covered carport in Jacksonville's Avondale neighborhood. Situated in an upscale neighborhood and only 3 miles from downtown. Conveniently located with a hip population and trendy bars & restaurants less than 0.3 miles away (walking distance). AT&T Fiber Internet. CNet says "Other connection types just don't compare to the performance of fiber internet." The home is furnished with ample cookware and dishware. A starter supply of paper goods and toiletries is provided.

The Jay

Nice little cozy camper with all the essentials. New super comfortable queen bed along with a nook that converts into a bed. Additionally, a 2 burner stove, fridge, freezer, microwave, sink, and an onboard shower with on-demand temperature control. There is a dedicated outside 1/2 bathroom for your use as well along with outdoor fireplace, grill, dining, and lounge area. I accommodate adults 18+ Pool rules: -Swim at your own risk -No diving -Please use outdoor shower before bathing

Beach Oasis Jacuzzi

Welcome to your own private oasis! This beach house is perfect for a relaxing getaway. Take a soak in the outdoor Jacuzzi/ outdoor shower, ride the bicycles along the coast, or catch some waves with the surfboards provided. The house comfortably sleeps eight people and includes a full kitchen, washer/dryer, and a cozy living room. Stay connected with 1 gigabyte of wifi for all your online needs. Book your stay now and experience the ultimate beach vacation!

Driftwood 2/1 w Firepit- 10 mins to MAYO & Beach

This 2 bedroom, 1 bath home is nestled in an extremely safe neighborhood and comes with a dedicated work space. The Driftwood Inn is perfect for up to five travelers looking for an economical stay close to the beach and the popular River Side. The backyard has a fire pit for the uncommon chillier nights in Florida and enough yard space for your fur baby to run around and play! Our kitchen is fully stocked for all your needs both short term and long term.

Palm Villa: Pickleball, Playground & Dog Park

Transport to this Talum inspired peaceful townhouse. Brand new construction townhouse located in a residential neighborhood. With three spacious bedrooms and five beds in total, we can accommodate groups comfortably. There is high-speed wifi and smart tvs for your streaming needs. The community features 2 children’s playgrounds , 2 dog parks, and an outdoor volleyball court all within walking distance.