Smoking-friendly holiday rentals in Gulfport

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.

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.

School Bus Turned Tiny Home

ECO FRIENDLY! Converted school bus now luxurious 1 bedroom tiny home that comfortably sleeps 4 large adults. Parked at a glass blowing studio in the warehouse arts district in St Pete. Perfect for 2nd Saturday art walk. 2 blocks from Tropicana field, breweries & restaurants. Directly behind the pinellas trail. 15 minutes to the best beaches. Enormous yard for outdoor activities. Built to go off grid, but stationed in the heart of the city. Urban camping at its finest!

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.

Studio Bedroom - Private Bathroom , Full Kitchen.

Enjoy your stay in Clearwater, Florida in our cozy studio suite! This sanctuary is a place for you to relax, reset and revive yourself. It is a mini-retreat especially designed for you to come alone, or with a friend or partner. This studio is centrally located near downtown and a a short drive from the beaches. Don't want to go out? Enjoy your stay in our tiki patio which includes a jacuzzi, dining area, seating area and television!

Lux Mid-Century Downtown Courtyard+Parking

Private Mid-Century Palm Springs-inspired duplex in downtown St. Petersburg, just a short walk to everything! Featuring one-of-a-kind mid-century modern architecture, a spacious family room, luxurious king bedroom, full kitchen, laundry, and stylish bathroom. Private, fully fenced courtyard with secure parking. Relax in this safe, modern getaway with mid-century vibes and all the comforts of home!