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•Early Check in•Lakefront•Salt Water Pool

"I 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 🛏️A premium $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

Couples clothing optional escape hot tub nude deck

You'll love this unique and romantic escape. Designed to create an intimate setting to enhance your time together. The RV is quite large and fully equipped . Master bedroom features a cashmere topped California king bed. The property has so many amenities starting with a very large pool, lighted at night. A dock on the river to enjoy the views. Access to kayaks on premises. There’s a private clothing optional area/deck with a massage table , hot tub and loungers. We recently added a fire pit

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.

River City Cottage

Cute cozy cottage in Jacksonville, Florida! Discover one of our most beloved and walkable areas . This stylish 2-bedroom, 1-bathroom home is thoughtfully designed to provide everything you need for a comfortable stay. This home is tailored to meet your needs. From its warm and inviting decor to its modern amenities, every detail has been carefully considered to create a peaceful and functional retreat. Relax in the rocking chair on the front porch and enjoy a sunset and fresh air.

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

Cowford Cottage

Historic walkable neighborhood, close to the Shops of Avondale for fine dining or the Murray Hill District for nightlife. Enjoy a short walk to Boone Park for its many amenities. Blocks from the Beautiful St Johns River, minutes to Downtown. Home features a spacious kitchen, a covered outdoor patio with bar and TV perfect for grilling, entertaining or watching the game. Sleeps 5. Pet friendly/fenced yard. Dedicated office space with strong Wifi and dual monitors.

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.