Smoking-friendly holiday rentals in Pinellas County

Private & Cozy Tiny Home/Cottage

This is a cozy converted workshop with all the amenities of a traditional home! You'll have a comfy bed that sleeps 2 with an air mattress upon request, TV with streaming options, fun decorations, WiFi, air conditioning, W/D, closet space, cooking stuff, & bathroom. If you love tiny homes, you'll love this. Because of it being a converted workshop, it still has that feeling in some regard. It's a little rustic, but still charming. It's not a hotel, nor does it try to be. Pets are welcome.

NEW Luxury Casita w/Hot Tub, Fire Pit, Backyard🏝☀️🏖

Welcome to Casita Citron, a beautiful new tropical paradise in the heart of St. Pete! Tranquil & centrally-located: close to nature trails, shopping, downtown St. Petersburg, & Tampa. Minutes to St. Pete Beach, ranked #1 in USA! Washer & dryer on site. Private fully fenced in backyard with fire pit. Luxurious hot tub spa with speakers, water shooters, & LED lights. Heated outdoor shower. Memory foam mattress. SmartTV. Second queen size bed available upon request (AeroBed with foam topper).

Shipwreck Bungalow

Shipwreck Bungalow, your own private paradise! Nestled in a quaint Gulfport neighborhood. Just 10 minutes from St. Pete beach, 10 minutes from lively downtown St. Pete and a few short minutes from funky downtown Gulfport. The Bungalow is surrounded by palms, tropical plants and flowers, beautiful outdoor shower, Tiki bar, heated stock tank pool, fire pit, outdoor games, grill and spacious outdoor seating area. Enjoy lounging by the pool or exploring all this sunny area has to offer!

TheGlampingGarden, Couples&Singles Retreat

Thats right pack your bags, it's time to get away to the clear ocean water and white sand. Come on you deserve it! You won’t forget your time in this romantic, and memorable place. We got bees buzzin, birds chirping, butterflies floating, and flowers blooming. Thats not all.... Our 2023 Glamper has ice cold ac to keep you cozy on hot sunny days. We are offering a totally relaxing experience, The Glamper is fully stocked with everything you need. Only a few mins from the Beach Strip.

StPete 420 cottage $FREE Parking$

This space is newly renovated, with some Key West inspired charm. Basic starter items provided. 2 rolls toilet paper & paper towels. Shampoo/conditioner/body wash Towels and linens. Longer stays are welcome! Air purifier running 24/7 keeps the place smelling great! Ashtrays provided. 420 encouraged :) nothing is shared! You have your own private entrance, into a super cute studio apt. (Unit c)! Private patio . We are 420 friendly & small DOG friendly! 10% off at the smokeshop.

5th Ave Downtown Oasis

Welcome to your urban getaway in the heart of St. Pete! This stylish Airbnb is located just a short walk to Central Ave’s vibrant bars, restaurants, and shops. Enjoy the convenience of downtown living with all the best local spots right at your doorstep. After a day of exploring, relax on the cozy outdoor patio—perfect for unwinding in the Florida breeze. Whether you’re here for nightlife, dining, or just soaking up the city vibe, this is the ideal spot for your St. Pete stay!

The Mahi on Madison 10 MINS FROM CLEARWATER BEACH

Come relax at this stunning, private, and newly renovated home with a welcoming, bright and cheery feel. Enjoy the exclusive privacy of a fully fenced in yard equipped with a hot tub, hammock, fire pit, grill, shaded lenai, and 3,200 sq ft of artificial turf (including mini putt putt) for games and activities. The Mahi on Madison is close to lots of shops, bars, restaurants, Clearwater Basin Marina, and just 10 minutes from Clearwater Beach.

Beautiful Guest House in Historic Old Northeast

Completely Detached Studio apt/Mother in-law suite located in Historic Old Northeast. 100 feet to Coffee Pot Water Way and walking path. Less than a mile to downtown, less than a mile to Vinoy Hotel and Beach drive; Quarter mile to North Shore Park. Two bikes are available to guests. Guests are also welcome to the lap pool, the grill, patio furniture. Must be okay with dogs.

New York

Take a break at this unique and tranquil getaway. This is a romantic place with all that you need to surprise your partner, all you have to do is to bring your bottle of wine. It is very central and near everything, including Tampa international airport, the beach 🏖 , Bush garden and many others. Just book this beautiful suite and you won’t regret for sure.