Smoking friendly holiday rentals in Sarasota County

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.

Flat in Sarasota

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.

4.75 out of 5 average rating, 60 reviews

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.

Flat in Sarasota

~ 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.

A screened-in outdoor space features a sparkling pool surrounded by lounge chairs and tropical plants. The area includes a seating arrangement with decorative cushions and a patterned area rug. Bright blue skies and lush greenery complement the inviting atmosphere of relaxation.

4.85 out of 5 average rating, 39 reviews

Welcome to "Casa Amarilla"

This is a 30 day rental. The whole family can relax in this peaceful oasis. Casa Amarilla is all about outdoor space & peaceful living. We have everything you need to make the best of your time in Sarasota. Our outdoor space provides you with a 1 stop vacation spot. Our lanai includes a pool(not heated), tv, eating area, relaxing area, a Jacuzzi (NOT AVAILABLE mid May thru mid Sept), a bbq grill, & a recliner. Fenced in yard for small pets. 17 min drive to Siesta Key & 22 mins to the airport l

4.95 out of 5 average rating, 43 reviews

A cozy living area features a plush beige sofa, accented by green cushions, surrounded by light-colored walls and a leafy area rug. Bright natural light enters through the window, complemented by white blinds and green curtains. A wooden coffee table and armchair add to the welcoming design.

Flat in Sarasota

Serene Getaway Near Downtown & the Bay!

Nestled within the Historic Cocoanut District, this vibrant neighborhood boasts diversity and an electric atmosphere. Locally favorited restaurants offer tantalizing treats just a stroll away, while the renowned Ringling Museum of Art beckons nearby. Positioned just a block from the serene Sarasota Bay and newly added Park. This suite is one of four within a tranquil courtyard. Ideal for remote work, alfresco dining, fireside chats, sun-soaked relaxation, or socializing with fellow guests.

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, 13 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 Yard~Peaceful Location

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.

Guest house in Port Charlotte

A well-lit guest room features a spacious bed with a patterned quilt and neatly arranged towels on top. A small table and chairs are positioned in a corner, and wall decor adds subtle character to the space.

4.8 out of 5 average rating, 69 reviews

Private Affordable Suite

Relax at this cozy place to stay in Port Charlotte. Close to some beaches, malls and parks ten minutes away from “Myakka River State Park”,. Close to Rotonda West! Englewood! There is a space to park. The bedroom has its own entrance. The bathroom is next to the room. The bathroom is private. The room is ready to be rented, the kitchen is not included..The laundry is included and it is shared with the owner..You can wash and dry once a week. Lots of wildlife.

4.96 out of 5 average rating, 53 reviews

A tropical hut features a thatched roof and ambient lighting, creating a serene atmosphere. Two lounge chairs are positioned under the shelter, and a wooden bed is visible in the background. Palm trees outline the area, enhancing the private outdoor setting.

Hut in Port Charlotte

Coco Plum

Glamping paradise feel the warmth of this tropical haven. Located on a fresh water canal full of fish. A peddle boat and kayaks available. Separate Bath House, fridge, coffee maker,outdoor cooking by heated pool, hot tub ,lounge chairs for sunning. Electric blanket, canopy screened bed. Comfy robes. Mini bar.fire tv, wifi Bikes are also available. No children No pets. All will find sanctuary here, Honeymooners, Gay, Nudist, any color. Veteran owned!!

An aerial view showcases a tranquil pool area surrounded by lush landscaping. Comfortable lounge chairs are positioned around the curved pool, accompanied by several shaded umbrellas. A covered seating area and palm trees enhance the inviting outdoor space.

4.89 out of 5 average rating, 18 reviews

Modern Escape with Pools Near Sarasota’s Best!

Furnished modern townhome with 2 bedrooms, each with private bath, full kitchen, Smart TV, washer/dryer, and screened lanai. Enjoy a peaceful, family-friendly community with 2 pools, sports courts, trails, lake, and dog park. Pet-friendly (maximum 1 pet up to 55 lbs or 2 small pets up to 20 lbs each). Minutes from Siesta Key, Lido Beach, The Ringling, and more. Safe, quiet, and highly rated,5-star guest reviews highlight comfort, location, and lifestyle.

4.99 out of 5 average rating, 284 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.

Flat 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...

Townhouse in Port Charlotte

A tranquil bedroom is featured with green walls and a wooden bed frame, adorned with ocean-themed bedding. A nightstand holds a decorative lamp. An assortment of seashells and a starfish are showcased on the bedding, enhancing the coastal vibe.

4.95 out of 5 average rating, 117 reviews

Exotic Escape home! w/ Heated Pool & Luxurious Spa

Discover a relaxing, tropical lifestyle on Florida's Gulf Coast. Located in the center and boarder of North Port and Port Charlotte you are close to shopping, beaches, restaurants, game fishing, dinner theaters and golf courses. This home is the perfect combination of quiet beauty, lively activity and friends to share it with. So look no further! We have your perfect get away!

An aerial view of a single-story home with a blue exterior and a metal roof highlights a private pool surrounded by a spacious patio. Lush landscaping and palm trees create a tropical atmosphere, while a shaded seating area under the umbrella invites relaxation.