Smoking friendly holiday rentals in Hillsborough County

4.8 out of 5 average rating, 217 reviews

The property is situated along the riverbank, featuring a two-story building with a balcony and palm trees nearby. A dock is visible with multiple boats moored, creating a serene riverside atmosphere.

Guest suite in Tampa

The Borough Riverside Retreat

Located on the Hillsborough River in the heart of Tampa. Stores, parks, restaurants and bars within walking distance. The private suite is smaller in size but warm and cozy, it has a queen bed with luxuries likens Jacuzzi tub, a Kitchenette with a mini fridge, microwave, toaster oven, , HD TV, Ice Cold A.C. and more. The property has a heated swim spa, firepit , swing area w/ hanging bed, hammock, fishing dock, outdoor shower, kayaks, Jon boat, bikes, lawn chairs to catch some rays and more..

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.

Guest house 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.

Guest house 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, 879 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.

Guest house 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, 373 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).

4.95 out of 5 average rating, 106 reviews

The exterior of a well-maintained single-family home features a two-car garage, manicured lawns, and palm trees. A gravel driveway leads to additional parking beside the house. A small garden area with shrubs and decorative stones enhances the curb appeal.

Home in Apollo Beach

Apollo Beach is your getaway destination!

Receive a $25 gift card when you book this Tampa luxury private retreat. Just minutes from Apollo Beach Nature Reserve, Manatee Viewing Center, Downtown, Riverwalk, Busch Gardens, Florida Aquarium, & more! The perfect spot for family & friends, to relax or if you just want to enjoy a great chartered fishing trip sightseeing shopping and let's not forget our beautiful beaches Apollo Beach is just minutes from the interstates for quick easy access for whichever direction you want to travel

4.98 out of 5 average rating, 200 reviews

A vibrant blue tiny house exterior is visible, featuring large glass double doors that lead inside. A green grass mat is placed at the entrance, and a hot tub is situated to one side, surrounded by a patio area and mature trees.

Guest house in Tampa

ZERO Cleaning Fees - Hot Tub Tiny House

Welcome to the Tiny Heights! Our quaint little tiny house features exclusive hot tub access, a full kitchen, private bathroom, shower and sink, wifi, AC, TV, Apple TV, and a beautiful private patio seating area. Tiny Heights Airbnb is located in the Seminole Heights area of Tampa and is within walking distance to an awesome selection of restaurants, bars, breweries, coffee shops and shopping. Just 4 miles from T.I.Airport and 2 miles from Raymond James Stadium, Ybor City & Downtown Tampa

4.89 out of 5 average rating, 134 reviews

A light-filled living area features a cozy seating arrangement with a tufted chaise lounge and an armchair. An elegant coffee table sits center stage on a textured rug, accompanied by decorative plants and wall art. Natural light filters through large windows, enhancing the inviting space.

Bungalow in Tampa

TAMPA/Seminole Heights/Walk 2 Breweries

This property is located in the trendy and historic neighborhood of Seminole Heights in Tampa, known for its abundance of cafes, bars, and restaurants. Just a 10 min drive to downtown, Amalie Arena, Riverwalk, Tampa General Hospital, Ybor City, and Armature Works. A 15 min drive to Busch Gardens, Hard Rock Casino, and 40 min to the beaches. Explore the area with Brew Bus while enjoying drinks. Overall, location offers easy access to some of the best dining and entertainment options.

4.95 out of 5 average rating, 256 reviews

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.

Guest suite in Tampa

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.

4.93 out of 5 average rating, 156 reviews

The exterior of a modern tiny home is framed by vibrant greenery and colorful decor. A red umbrella shades a patio area with two red chairs, while a sliding glass door provides a glimpse into the inviting interior.

Tiny home in Lutz

Tiny Lime House, Cozy Modern Bright Garden Retreat

Modern, minimalist, tiny home with artistic decor. This property has mature oaks, many windows and natural lighting. There is outdoor dining, hot tub, lounge chairs, fire pit, fishing pond, and an extensive garden for nature lovers. Shopping (10 mins), USF (15 min), Busch Gardens/Adventure Island (20 min), Clearwater Beach (45 min), Raymond James Stadium (30 min), TPA (35 min), downtown Tampa (30 min), Ybor (30 min), Disney (1.5 hr). Please give us a call if you have questions.

4.85 out of 5 average rating, 395 reviews

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.

Flat in Tampa

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.

4.99 out of 5 average rating, 102 reviews

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.

Home in Tampa

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!