Smoking-friendly holiday rentals in Sarasota

4.97 out of 5 average rating, 235 reviews

A compact sleeping area is furnished with a wooden bed frame and a colorful assortment of throw pillows. A modern air conditioning unit is mounted above, while a bedside table holds a lamp. Light streams in through the window adorned with wooden blinds.

Apartment in Bayou Oaks

Modern Private Apartment 1 Block from Sarasota Bay

One block from Sarasota Bay - completely remodeled and fully furnished guest apartment with a Miami deco feel. The unit is a little over 300 sf with full kitchen, one bathroom w/ shower, comfy queen bed, several stools/ chairs, flat screen tv, wifi, off-street parking, six USB ports for easy charging and sitting area outdoors on front porch. Five minutes to downtown or SRQ airport, 15 minutes to Lido Beach, and 25 minutes to Siesta Beach with easy access to University Parkway or Fruitville Rd.

A quaint outdoor patio area features a small table topped with a bottle. A vibrant blue umbrella provides shade, while a floral-patterned chair invites relaxation. Surrounding greenery includes a potted plant and well-maintained shrubs, creating a serene outdoor space.

4.75 out of 5 average rating, 61 reviews

~ Cozy Apartment Close to Siesta Key ~

Enjoy this cozy, small 1-bedroom apartment attached to our home, separate entrance, in a quiet neighborhood, and within walking distance of a nature preserve. Relax in the living room on a comfy couch, or open the French Doors and enjoy the patio. Extra TV in a bedroom. We have made an enhancement and health safety improvement in our central air conditioning unit for mutual peace of mind. We have installed a CleanCoil UV unit that has been proven to eliminate 99% of viruses, bacteria, and mold.

4.95 out of 5 average rating, 226 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.

4.92 out of 5 average rating, 132 reviews

Olympic Oasis | GYM • POOL • GAMES • BBQ • GAINS

Welcome to Olympic Oasis, your tropical training ground meets resort-style getaway. Start with a gym sesh in your private gym, then reward yourself with a cooling dip in the sparkling pool. Sink into chic loungers or relax in serene spaces crafted for total tranquility. Feeling playful? The arcade awaits. Feeling photogenic? We’ve got the perfect backdrops. All this sits in Bradenton’s prime location, close to pristine beaches & the best hot spots. Work hard. Play harder. Vacation hardest.

In the foreground, a hammock rests on a sturdy stand, placed on lush green grass. Nearby, two kayaks in vibrant red and blue are positioned side by side, with a glimpse of a boat dock visible in the background, surrounded by tropical vegetation.

5 out of 5 average rating, 101 reviews

Manatee Cove: Waterfront Oasis w/GameRoom &HotTub

Welcome to Your Private Waterfront Oasis! This spacious home on a serene canal off Sarasota Bay features 3 bedrooms, 2 bathrooms & a HUGE climate-controlled game room! Enjoy direct water access for fishing, canoeing, kayaking and spotting manatees. Just 7 minutes from the airport & 15 minutes from Sarasota, you’ll have access to beautiful beaches like Siesta Key & Anna Maria Island. Offering free WiFi, BBQ grill & firepit, this retreat is perfect for families seeking relaxation & adventure!

A cozy living area features a gray sofa positioned against a wall, complemented by a patterned area rug. A round glass coffee table sits in the center, and a lamp provides soft lighting. Natural light filters through the window, with muted white curtains enhancing the ambiance.

4.87 out of 5 average rating, 133 reviews

Cozy Golf, IMG, Country Club & Anna Maria Island

Peaceful Villa retreat walking distance from Golf Country Club, close to IMG Academy, Anna Maria Island and Beaches. Convenient located near restaurants, grocery stores, movie theater, Robison Preserve and beaches. 2 Bedrooms. 3 beds (1 queen, 2 full and pull out couch for extra guess - sleep 6). Screen lanai with hot tube. Running trails close by and endless beaches with amazing sunsets!!! Come and check out this little piece of heaven call Bradenton. 10 minutes from Ana Maria Island,

A well-lit bedroom features a spacious bed with a light-colored bedspread. Two large windows offer views of the outdoors, framed by sheer curtains. A ceiling fan hangs above, providing airflow. A comfortable chair and a dresser add practical elements to the inviting space.

5 out of 5 average rating, 16 reviews

The Palms Away

This special place is close to everything, making it easy to plan your visit. 1 mile to Siesta Key. Built in the 50's but totally renovated to today standard's. Heated swimming pool, but if the water gets to hot the heater will also cool the pool. Very close to shopping. Large deck with view to tropical garden and waterfall. Gas fire pit with built in seating. Small putting green and Corn-hole game are available for your use. 5 TV's with wi-fi. A Gazebo with plenty of sitting area.

4.97 out of 5 average rating, 140 reviews

A serene sunset is captured over the pool area, with vibrant purple and orange hues filling the sky. Illuminated palm-style lights adorn the seating area, creating a playful ambiance. Comfortable seating is arranged with colorful cushions, inviting relaxation amidst the peaceful backdrop.

Home in Port Charlotte

Big Pool~Outdoor TV~Private Oasis~Gorgeous Sunsets

Big heated pool is private from neighbors. Full sun on the pool from noon to sunset. Covered lanai provides relief from the sun. BBQ & watch football on outdoor tv while the kids swim & play. Enjoy beautiful sunsets overlooking a peaceful park-like setting. Walk the golf cart paths, work on your tan, read a book, play music, sip on tropical drinks & float all your cares away. Have your morning coffee outside & listen to the birds sing. Outdoor living is what it’s all about here.

4.85 out of 5 average rating, 102 reviews

A cozy sleeping area features a spacious bed with white bedding and decorative pillows. A folded blanket is draped over a chair in the corner. Side tables flank the bed, enhancing functionality. The room is illuminated by soft lighting and a ceiling fan, with dark curtains framing the window.

Guest suite in Bradenton

Cozy For Two Getaway Bradenton

Welcome to our cozy retreat in Bradenton! Perfect for a couple, this small but charming space can comfortably accommodate our guests (ideally a couple and 2 small kids if pushing for 4 guests since the couch is small, but lays out). Enjoy the privacy of your own gated parking area. Located just 25-30 minutes from the beautiful Lido/Siesta Key Beach and Anna Maria Island, you can spend your days soaking up the sun and exploring the vibrant local scene here!

4.99 out of 5 average rating, 341 reviews

A pathway made of stone leads to a light green structure nestled among lush foliage. Tropical plants and vibrant red flowers surround the pathway, creating a serene outdoor setting under a clear blue sky. The area is shaded by tall trees, enhancing the peaceful ambiance.

Tiny home in Sarasota

Unique tropical stay - 5 minutes to Siesta Key

Welcome to “The Stream” — a hidden tropical retreat tucked away in the heart of Sarasota. This one-of-a-kind space offers the perfect blend of seclusion and convenience. Just 5 miles from the world-famous Siesta Key Beach and 3 miles from downtown Sarasota. Stroll or bike to nearby cafés, acclaimed restaurants, boutique salons, Publix, Trader Joe’s, CineBistro, and more. Whether you’re here to unwind or explore, “The Stream” is your private paradise.

4.99 out of 5 average rating, 290 reviews

An outdoor dining area features a round table with a vibrant red centerpiece surrounded by four black iron chairs. The space is shaded by a pergola, adorned with decorative curtains and greenery, creating a serene setting among the natural elements.

Apartment in Englewood

The Oz Courtyard 2.9 mi beach

The Oz House is old and funky... The Courtyard is a magical place with its own private garden, outside shower and gas grill . The pergola has a two person swing and night blooming Jasmin. Your own hammock and chimera all privately set away from the rest of the Oz House. The pool and hot tub are in the main gardens shared by all who visit Oz It’s a wonderful getaway for anyone wanting to just BEE...

An aerial view showcases the tranquil neighborhood surrounding the luxurious retreat. Lush greenery and palm trees fill the landscaped yards, with Sarasota Bay visible nearby, offering a scenic backdrop. The area features winding streets and well-maintained homes, highlighting the beauty of coastal living.

4.95 out of 5 average rating, 111 reviews

Free Htd Pool • Steps to the Bay • Pet-Friendly •

The Bay 218 is a stylish one-level Sarasota retreat just steps from the bay and minutes to Lido Key, Siesta Key, Longboat Key, and Anna Maria Island. Enjoy a chef’s kitchen, two living areas, luxe bedrooms, and a private backyard with heated pool, tanning ledge, and kids play area. Beach gear included. Dog-friendly with approval. Perfect for a relaxing coastal getaway! 🌴🏖️

Popular amenities for Sarasota Smoke-Friendly Accommodation

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Smoking-friendly apartment rentals

4.96 out of 5 average rating, 77 reviews

An inviting saltwater pool features a connected spa surrounded by well-maintained landscaping. Poolside, two lounge chairs and a small table are positioned for relaxation. The patio is paved with light-colored stones, creating a serene outdoor space for enjoyment.

Apartment in Venice

Indigo at the Beach 21!

4.99 out of 5 average rating, 78 reviews

A bright and airy living space features a neutral sofa, an accent table, and a coffee table, all set against light wood flooring. A ceiling fan aids ventilation, while a large window allows natural light to fill the area. The open kitchen displays modern appliances and bar seating.

Apartment in Venice

Venice Island Pool Casita with 2Bedrooms/2 Baths

Apartment in Bradenton Beach

A dining area is presented with a light wooden table surrounded by woven chairs. A round basket sits in the center, filled with fresh fruit. Green placemats adorn the table, while natural light streams through a nearby window, highlighting the simple decor of the space.

5 out of 5 average rating, 6 reviews

LasPalmas Beach Rentals,3

4.75 out of 5 average rating, 16 reviews

A spacious living area features a large coffee table in the center, surrounded by light-colored wood flooring. A sectional sofa sits to the right, while modern appliances, including a refrigerator and microwave, are visible in the kitchen. Large glass doors open to a private outdoor patio area.

Apartment in Siesta Key

Gertrude Siesta | 8-steps Beach Path, Low-Price

4.85 out of 5 average rating, 34 reviews

Beautiful and cozy because we care

New place to stay

Spacious and comfortable Siesta Key 2BR

4.96 out of 5 average rating, 45 reviews

Lido Key Getaway Near Downtown & the Bay!

5 out of 5 average rating, 37 reviews

A two-story home is visible across the calm waters, featuring a covered balcony with railings and palm trees adorning the front yard. A dock extends into the water, accommodating a watercraft and offering access to the bay.

Apartment in Palmetto

Waterfront Studio relax, work on Snead Island, Fl.

Smoke-Friendly Holiday Houses

Superhost

A charming single-story home is surrounded by palm trees and lush greenery. The exterior features light-colored siding and multiple windows, allowing natural light to fill the interior. A vibrant red door adds a pop of color to the welcoming facade.

Home in Bellevue Terrace

4.57 out of 5 average rating, 7 reviews

Cozy Cottage, 2 Bedrooms, 1 Bath in Sunny Sarasota

4.97 out of 5 average rating, 31 reviews

Home in Holmes Beach

Ocean72 | Heated Pool & Spa | 2BR Near Beach

4.9 out of 5 average rating, 29 reviews

Home in Port Charlotte

Marina/Heated Pool/Hot tub/Canal/Game room/14PPL+

An aerial view captures the charming waterfront home with a manicured yard featuring lush greenery. A private dock is visible along the water, with kayaks stored nearby. The house is complemented by a spacious patio area and steps leading to an inviting entry.

5 out of 5 average rating, 42 reviews

Waterfront Retreat | Heated Pool & Boat Dock

Superhost

The two-story home is framed by lush greenery, showcasing a combination of wooden and stone exterior. A wrap-around deck is visible on the upper level, while the lower level features large windows and a paved pathway leading to the entrance.

4.88 out of 5 average rating, 32 reviews

Tropical Escape, Sarasota!

5 out of 5 average rating, 32 reviews

Grotto Pool Oasis | 3BR Near IMG & Beaches

An open living area is showcased, featuring a spacious sectional sofa and a coffee table. A large TV is mounted on the wall, with a stylish media console beneath. A dining table with chairs is visible, illuminated by natural light from the nearby windows.

4.95 out of 5 average rating, 20 reviews

The Lovely Family House