Smoking-friendly holiday rentals in St. Petersburg

4.99 out of 5 average rating, 351 reviews

The image captures a serene outdoor area featuring a charming entrance to the cottage. Surrounding tropical plants and tall trees create a lush environment. A decorative fountain stands to the left, and comfortable seating under an umbrella adds to the inviting atmosphere.

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.

4.82 out of 5 average rating, 103 reviews

A spacious screened-in pool area is highlighted, featuring a clear blue pool surrounded by a patio with lounge chairs. A modern kitchen and living room are reflected through large glass doors, connecting indoor comfort to outdoor relaxation.

Home in Largo

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

4.94 out of 5 average rating, 181 reviews

A spacious yard features a white hammock hung between palm trees, surrounded by lush artificial turf. Soft ambient lighting highlights a cozy outdoor area, and the inviting home can be seen in the background, showcasing a seamless flow between indoor and outdoor spaces.

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!

4.95 out of 5 average rating, 223 reviews

A charming pool area is surrounded by lush tropical foliage. The turquoise saltwater pool is framed with light stone paving. A small cottage with a red door is visible in the background, while lounge chairs and a colorful beach ball provide inviting accents to the outdoor space.

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.

Home in Southeast Seminole Heights

The exterior of the historic farmhouse showcases a neatly landscaped yard with vibrant green hedges and palm trees. A brick pathway leads to the welcoming entrance, featuring a red door and black rocking chairs on either side, creating an inviting atmosphere.

5 out of 5 average rating, 191 reviews

Multi-Award Winning & Top 5% Rated on Airbnb 2025

“The Pickett Fence” is a recognized Historic Farmhouse Inn that was built in 1920’s. ~SORRY, NO CHILDREN!~ Included: *Free WiFi *FireStick, Netflix, Hulu, Peacock, MAX *Paramount+ *3 large bedrooms W/TV & Fire-stick *2.5 baths *Chef Gourmet Kitchen & amenities *Private Hot-tub for 6 with Bluetooth Only minutes away to- 😍 Ybor Downtown Amalie Arena Convention C. Riverwalk Raymond Stadium Adventure Is. Busch Gardens USF T.I.A International Mall Westshore Mall 20-25 Minutes to- Beaches

Guesthouse in St. Petersburg

The exterior of a cozy converted workshop features a gray wood-paneled facade with a vibrant yellow front door. Two chairs are positioned on the porch, beside a barrel and trash bins. A privacy fence can be seen in the background, surrounded by greenery.

4.84 out of 5 average rating, 880 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.

Guesthouse in St. Petersburg

A well-designed fire pit area is surrounded by vibrant landscaping, featuring five blue adirondack chairs positioned around a stone circle. Lush palm trees provide a tropical ambiance, and a gravel path leads to the space, inviting relaxation in the private backyard.

4.84 out of 5 average rating, 376 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, 136 reviews

A heated stock tank pool is surrounded by a lush tropical landscape featuring a variety of green plants. An oversized umbrella provides shade, and a colorful bungalow is visible in the background, creating a serene outdoor retreat.

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!

Guest suite in Southeast Seminole Heights

A charming exterior showcases a guest suite with a vibrant red door, surrounded by lush greenery. The patio area features seating among potted plants, and a wooden pergola provides shade, enhancing the inviting outdoor space. Brick paving leads up to the suite's entrance.

4.95 out of 5 average rating, 257 reviews

The Little Pink Guest Suite

Enjoy our cozy back yard guest suite. Fully fenced in by a privacy fence with dedicated off street parking. Our space is walking distance to some of the best bars, coffee shops and restaurants in Seminole Heights. Inside you'll have a fully equipped kitchenette, very comfy brand new Queen size bed, Smart TV, and fast internet. We have all you need to provide comfortable stay for vacation or business travel right in the middle of the city with quick access to everything via car.

4.9 out of 5 average rating, 107 reviews

A cozy outdoor area is enhanced by a fire pit surrounded by multiple seating options. The pool glows invitingly under the evening sky, with soft lighting strung above. A sun shade protects this relaxing space, creating an ideal setting for gatherings.

Home in Clearwater

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.

Apartment in Tampa Heights

A welcoming living area is furnished with two orange chairs and a round side table, positioned on a plush area rug. A large TV hangs on the wall opposite a comfortable bed, with light streaming through sheer curtains. The space features a blend of modern and cozy elements.

4.84 out of 5 average rating, 397 reviews

Downtown Tampa & Armature Works Apartment!

Stylish, 2-bedroom, studio apartment just blocks from downtown Tampa! Sleeps 4 with a king bed and cozy full bed. Enjoy a dedicated office space, fully stocked kitchen with coffee bar, in-unit washer/dryer & a balcony overlooking the lush courtyard with seating & a grill. Nestled in a peaceful neighborhood yet minutes to Dowtown Tampa, Ybor City, Armature Works & much more—your perfect Tampa escape! The second bedroom is accessed through the main bedroom, separated by a door.

A spacious outdoor area features a heated saltwater pool and hot tub surrounded by lush greenery. A fire feature adds warmth to the setting. The enclosure allows for comfortable relaxation while enjoying an inviting atmosphere.

4.99 out of 5 average rating, 104 reviews

Heated Salt Pool & Spa | Near Airport & Downtown

Tampa Oasis - 3BR/2BA(Half Bath with outdoor shower with hot water), Heated Pool, and Hot Tub (Saltwater) Welcome to convenience and relaxation near Tampa Airport! This 3-bed, 2 bath home comfortably sleeps 8 with a pullout bed. Enjoy a heated pool, hot tub, and outdoor shower + TV. Proximity to the airport, Tampa's attractions, and more. Amenities include Wi-Fi, washer/dryer, and smart home tech. Book now for a memorable Tampa stay!

Popular amenities for St. Petersburg Smoke-Friendly Accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

Apartment in Clearwater Beach

The property features a refreshing swimming pool surrounded by lounge chairs. A brick-paved patio includes tables and umbrellas for shade. The building is positioned near the Intracoastal Waterway, with a boat dock visible in the foreground.

4.85 out of 5 average rating, 46 reviews

Enchanted Inn Suite #3: Waterfront, Pool, Fishing

Apartment in Davis Islands

A balcony area is framed by a large arched opening, featuring a small round table accompanied by two chairs. Sunlight creates a patterned effect on the floor, while a tree is visible beyond the railing, offering a glimpse of the surrounding scenery.

5 out of 5 average rating, 9 reviews

One bedroom apartment

Apartment in Forest Hills

A spacious sleeping area features a neatly made bed with a patterned blanket. A black headboard adds contrast to the light walls, while a striking black and white lion portrait hangs above. A ceiling fan and door are visible in the background.

4.8 out of 5 average rating, 15 reviews

The paradise

Apartment in Downtown St. Petersburg

An open living space showcases a modern kitchen with stainless steel appliances and a dining table surrounded by sleek chairs. A comfortable sofa faces a mounted television and decorative electric fireplace, while a bright yellow armchair adds a pop of color to the neutral decor.

5 out of 5 average rating, 8 reviews

Downtown Zen 2-Bedroom Bungalow

Apartment in Historic Kenwood

A bright sleeping area is presented with a wooden headboard, featuring decorative pillows and vibrant bedding adorned with tropical motifs. Natural light filters through sheer curtains, adding a warm touch to the space.

4.9 out of 5 average rating, 20 reviews

StPete 420 cottage $FREE Parking$

Apartment in St. Petersburg

A private outdoor space featuring a fire pit surrounded by colorful adirondack chairs in orange and yellow. The area is covered with white gravel and enclosed by a white privacy fence, with green pet turf visible in the background.

4.99 out of 5 average rating, 88 reviews

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

Apartment in Indian Rocks Beach

The living area features a comfortable sectional sofa adorned with soft pillows. A coffee table made of natural fibers sits in front, complemented by a decorative arrangement of flowers. A wall-mounted television displays a serene ocean scene, while artwork and a potted plant enhance the space.

4.96 out of 5 average rating, 71 reviews

Hear The Waves | 5-Min to Beach + Hot Tub

Apartment in Ybor Heights

A serene pool area is framed by lush greenery and tropical plants. The sparkling water reflects the sunlight, while a stone deck surrounds the pool. Seating is provided at black metal chairs, and a shaded entertainment tent is visible in the background.

4.84 out of 5 average rating, 50 reviews

Casa VM Ybor Clothing Optional Guesthouse

Smoke-Friendly Holiday Houses

4.78 out of 5 average rating, 165 reviews

A spacious living area features a classic pool table in the center, surrounded by natural light from large windows. A dining table is visible in the background, while an open kitchen is accessible to the left. Warm lighting fixtures enhance the overall brightness of the space.

Home in Bay Crest Park

Your Tampa Bay Vacation Entertainment Home

4.86 out of 5 average rating, 231 reviews

An illuminated screened patio surrounds a glowing heated pool, with colorful lights highlighting the space. Lounge chairs are positioned for relaxation, while the outdoor seating area is visible in the background. The serene ambiance is complemented by the shimmering water.

Home in Clearwater

SaltedHeated pool 5BDR3Bath/9 min2ClBeach Sleep22

An open concept living space features a spacious kitchen with dark wood cabinetry and stainless steel appliances. Connection to a cozy seating area is provided by a light-colored sofa adorned with decorative pillows. A dining area with a red tablecloth and seating for six enhances the welcoming atmosphere.

4.82 out of 5 average rating, 130 reviews

5 star Tampa Pool Oasis 2

A bright kitchen area features modern white cabinetry and a large island with a grey granite countertop. Stainless steel appliances are positioned along the wall, and natural light floods in through a window overlooking an outdoor space. A contemporary light fixture hangs above the island.

4.86 out of 5 average rating, 267 reviews

3BR/2BA Cozy Tampa Home

4.95 out of 5 average rating, 77 reviews

A modern living area features a gray sofa adorned with patterned pillows, arranged near a round wooden coffee table with decorative items. The space is illuminated by a tall, artistic lamp, and two bright orange doors complement the warm color palette.

Home in Largo

Boho Vibes

4.96 out of 5 average rating, 27 reviews

A fully equipped kitchen is featured, showcasing modern stainless steel appliances and a spacious island with seating for four. Light-colored cabinetry provides a sleek look, while large windows allow natural light to fill the space, creating a bright and inviting atmosphere.

Home in Beach Park

Modern Nest in South Tampa

4.76 out of 5 average rating, 46 reviews

The outdoor space features a heated pool surrounded by sun loungers, offering ample relaxation options. Lush green landscaping and colorful plants enhance the ambiance. A screened-in lanai is visible, providing a shaded dining area for outdoor meals.

Home in Largo

Serena House w/ Heated Pool & Quick Drive to Beach

Spacious entertainment area features a pool table with a vibrant red felt surface, accompanied by a seating area with comfortable sofas. Large ceiling fans provide airflow, while multiple screens display various entertainment options, enhancing the communal space for family gatherings.

4.94 out of 5 average rating, 155 reviews

Villa White Rock in Tampa

Smoke-Friendly Holiday Condos

A spacious living area features a large sectional sofa and a television on a low stand. Natural light enters through a sliding door that leads to a patio, framed by a railing. The flooring is dark and smooth, enhancing the room's openness.

Condo in Town 'n' Country

Spacious 1 BR Near TPA

A spacious living area features a comfortable blue sectional sofa adorned with decorative pillows. A large wall clock and coastal-themed artwork enhance the decor. Light wood flooring complements the design, while a dining area is visible in the background, furnished with a table and chairs.

Condo in Indian Shores

4.85 out of 5 average rating, 26 reviews

Vitamin Sea 3 BDRM Complete Remodel DONE MAY 5

4.95 out of 5 average rating, 40 reviews

A wide sandy beach extends towards the horizon, meeting the ocean with gentle waves. Colorful umbrellas provide shade for beachgoers, who are enjoying the sun and water. Lush green grass borders the beach, creating a natural transition between the shore and the sandy area.

Condo in Treasure Island

Beverly's Beach Place - Gulf sand just steps away

Condo in Belleair Beach

4.82 out of 5 average rating, 51 reviews

Ground floor unit on the beach