Smoking-friendly holiday rentals in Pinellas County

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

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).

*POOL* Bar, Hottub, Central location

Welcome to Pat’s Pub House🌴 Pool, hot tub, & outdoor bar. Peaceful boho vibe. Nature lovers dream! Plants, crystals, & art everywhere. Kids fort with rock wall & sand box. TV you can watch from the pool! Movie projector room with huge comfy couch. Short drive to Florida’s ~BEST~ Beaches, John’s Pass, Downtown St. Pete, & Airports. Central location. 3 bedrooms, 5 beds, 2 baths, dining room, & 2 living rooms. Unique, fun, laidback house. Amazing backyard. Local family owned & operated.

California

Hi there , this beautiful studio apartment is a very romantic and peaceful place to stay., very central in one of the best areas in Tampa , also near Tampa internacional airpor, Publix , Walmart a few minutes away. The apartment has also a Murphy bed and a laundry both locked for a an extra charge (AS REQUEST FOR AN EXTRA CHARGE), So if you want to have a real good time in a comfortable studio apartment this is the place to stay -Second bed- 30 per day - Landry- ——$ 20

Kenwood Oasis

Message for open dates not on calendar. Spanish Mediterranean style with rustic charm and modern amenities compliment this homes beautiful exposed brick and stained glass doors. The outdoor living space is amazing with a screened in 30’x30’ breezeway for perfect FL living. Lush tropical landscaping, a great yard and tons of parking on a completely fenced in 1/2 acre lot and all the privacy guests could ask for. Located just 5 minute drive to Central Ave. Downtown St. Pete.

Spacious Home Solar-Heated Pool and Spa

We prefer a no-contact stay and NO PARTIES. Screened Solar-Heated Pool w/Spa, King Bed Master Suite w/42" RokuTV w/Pool Access, Dual Sinks, Living Room, 65" Samsung Cable TV, Queen Bed Second Bedroom w/55" TV and Direct Pool Access, , Dining Room, Laundry Room Washer/Dryer, 2 Driveway Park Spaces, Full Kitchen, Water Softener, Gas Grill, Porch, Wifi+Ethernet, up to 1350 sq. ft., King Trundle Bed (with room dividers) available in Common area to sleep 6.

Steps Away 1st Floor-Bikes/Beach Access/ WI-FI

This ground floor apartment is located in a nine-unit condo complex. It's a few minutes walk to the lighted public crosswalk that crosses Gulf Blvd to the Madeira Beach Public Beach Access. The 385 sq. foot unit is perfect for two people. We are a mile from John's Pass Village. Limited beach equipment, bikes, beach towels, Wi-Fi, and Smart TV's included. Wireless WI-FI. Security latch on door. Four people can stay but it would be tight.

The Mahi on Madison 10 MINS FROM CLEARWATER BEACH

Come relax at this stunning, private, and 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.