Smoking friendly vacation rentals in Gulfport

4.99 out of 5 average rating, 340 reviews

Guesthouse in Largo

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.

4.86 out of 5 average rating, 236 reviews

Home in Seminole

Orange Grove Cove ~ Bay Pines ~ Madeira Beach Area

1.5 miles to the beach! Charming, clean, remodeled home. We provide 2 bicycles, beach gear, chairs, cooler, beach cart, toys, & umbrella. Pinellas trail is only 1 block away! Comfy king beds in both bedrooms. Pool table in the sunroom, charcoal grill, & jet bathtub. Memory foam couch bed. Welcome to the lovely quiet neighborhood of Bay Pines, FL. Great central location! Near Madeira Beach, Treasure Island & John’s Pass. Locally owned & operated by highly experienced superhosts. Big Dog Friendly!

4.94 out of 5 average rating, 175 reviews

Home in Clearwater

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!

Apartment in St. Petersburg

4.99 out of 5 average rating, 83 reviews

Paws Paradise Studio-2 Miles to Beach-Kitchen-Yard

Dog friendly safe and secure Studio apartment with fenced yard and only minutes away from the great white sandy beaches of Treasure Island and St.Pete Beach. This updated space is great for short-term or extended stays. Outfitted with a mini kitchen and its own private entrance with covered patio and fire pit area. A 15 minute drive east is beautiful Downtown St Petersburg with its newly opened Pier. Walking distance to Walgreens and the very popular local favorite Deadbobs Bar. A 40" Roku tv.

4.95 out of 5 average rating, 221 reviews

Guesthouse 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.

Guesthouse in St. Petersburg

4.84 out of 5 average rating, 858 reviews

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.

4.79 out of 5 average rating, 215 reviews

Home in Clearwater

SaltedHeated pool 5BDR3Bath9 min2ClBeach Sleeps 22

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 from November through May free of charge

Guesthouse in St. Petersburg

4.83 out of 5 average rating, 349 reviews

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).

4.96 out of 5 average rating, 123 reviews

Tiny home in Gulfport

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!

4.77 out of 5 average rating, 155 reviews

Home in Bay Crest Park

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.

4.92 out of 5 average rating, 220 reviews

Home in Tampa

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.