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.

Colorful Bungalow Sleeps 6 - Pet Friendly!

This colorful, family friendly, pet friendly, bungalow provides beds to comfortably sleep 6 guests and is located on a quiet tree-lined street in the Historic Murray Hill section of Jacksonville. It features a full kitchen, and fenced backyard with charcoal grill. Enjoy the convenience of an eclectic mix of local restaurants, shops, bars and parks, within just a 10 min walk or a quick car ride. Easy interstate access to I-95 and I-10 and convenient to downtown Jacksonville and the Beaches.

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.

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.