Smoking friendly holiday rentals in Pinellas County

Mahi on Madison:Near Beach w/Fenced Yard & Hot Tub

Escape to this stunning, private, and beautifully renovated home that has a bright and cheerful atmosphere. Enjoy the exclusive privacy of a fully fenced yard, featuring a relaxing hot tub, hammock, fire pit, and grill. With 3,200 sq ft of lush artificial turf with a fun mini putt-putt course, there’s plenty of space for activities and fun! We're just minutes away from shops, bars, restaurants and the Clearwater Basin Marina. Best of all, the beautiful Clearwater Beach is only 10 minutes away!

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).

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!

*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.

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.

Your Tampa Bay Vacation Entertainment Home

This Entertainment Oasis to Enhance Your Tampa-Bay Vacation Experience with WiFi, Pool Table & Poker-Table, Every Room has a Smart TV, USB Chargers, Screen in Patio w/Pingpong Table-Dartboard-Grill, Backyard Privacy Fence. 3 BR, 2 Full Baths, 1-Air Mattress, 4-Car Driveway. Located Near Airport, RJ Stadium, International Plaza, Ben T David Beach, Clearwater Beach, Busch Gardens, & Adventure Island. Entertainment Book In The Home w/Beaches, Parks, Restaurants & Shopping.

Rooms with a Pool

Welcome to Tampa Bay! The home is central to everything Tampa Bay and is 1 hour 20 minutes from Orlando. This home includes a three guest rooms, 1.5 bathrooms, a living and a family room, kitchen, dining room, bar, office and a backyard lanai with a large heated pool area. You get the entire home and there is nobody else staying at the same time. It is in a quiet suburban neighborhood, about 40 minutes from downtown Tampa, Clearwater, and St. Petersburg.