Smoking friendly vacation rentals in Gulfport

Modern studio, pool & sauna | 10 min to DT & BEACH

Enjoy a stylish stay at this private studio within our family home. With private entry and dedicated parking, the studio has a kitchenette, private patio, fenced in space for outdoor living, and is pet friendly. There’s a queen bed and full size pullout sofa. The studio is stocked for hosting, beaching, or just relaxing with coffee and a book. As your hosts you might see us (or our pups!) around and we love to highlight the wonderful places between downtown St. Pete, Gulfport, and the beaches.

Heated pool & hot tub | 10 min to beach & DT

Enjoy a stylish stay at the centrally-located Pineapple Palace. Nestled between St. Pete Beach & Downtown St. Petersburg, this private mid-century pool home is a dreamy Florida vacation. There are 3 beds/2 baths with a spacious outdoor living area, screened in pool, outdoor bar, hot tub, and more. This space is perfect for vacations, bachelorette weekends, staycations, and events. For events, please DM the details. We’re excited to host you & share our unique guide to all things St. Pete! ☀️

Paradise Cottage Largo Beaches 1 mile High ground

We are PARADISE COTTAGE, and the standards of super host are status quo! We're ready for you! Although only 2 miles from the Gulf, we're on high ground! We are on a Priority One Energy Grid. With over 300 huge potted plants, many trees, etc we live in a lush tropical "Paradise". Our guests' highest praises include private, quiet, serene, safe and secluded; attributes we're fortunate to claim We have no neighbors while being so close to so much. Read the next section "The Space" to learn more.

Sunshine, Beaches & Refreshing Pool/Screen Patio

Step inside, you’re greeted by an open living area, and beautifully updated kitchen and appliances. Step outside to your private paradise! The large screened-in pool lanai beckons you to relax, lounge around, take a dip, fire up the grill and unwind in the Florida sunshine. This is where unforgettable memories are made. ☑ 5 mi to beautiful Sand Key Beach park and Clearwater Beach! ☑ 10 mi to John’s Pass Boardwalk. ☑ 9 mi to CLW/St Pete Airport & 23 mi to Tampa INTL. ☑ Sun room w/ping pong tabl

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!

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, New AC Unit, 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.

Watch the Sunrise at Sunrise! @ Clearwater home.

Heated pool!! Perfect place for a family vacation!! Start your day lounging by the pool or head to one of the many nearby beaches. Enjoy your day at pier 60 in Clearwater where there are many shops and places to eat also you may run into terry hogan on Mondays for karaoke night at his place “Hogan’s Hangout” or head on down to whiskey joes and enjoy live music, food and drinks all while sitting on the sandy beach next to a fire pit, end the day back at home relaxing by the pool.

SaltedHeated pool 5BDR3Bath/9 min2ClBeach Sleep22

This is the perfect vacation home for families! 5 bedrooms 3 full bathroom home with a screened and HEATED Pool, screened covered patio with sitting area and big outside dining table for gatherings and overall enjoyment of the outdoor spaces. Strategically located 10 min from the famous Clearwater beach, less than 10 minutes to bellair beach13 minutes from Indian Rocks beach it is in a prime location with many events happening nearby. Pool heated free of charge by request