Smoking friendly vacation rentals in Sarasota County

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.

4.97 out of 5 average rating, 232 reviews

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, 56 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.

5 out of 5 average rating, 6 reviews

The exterior of a charming studio is showcased, featuring a light yellow facade and a wooden porch area. A small table is positioned near the entrance, and air conditioning unit is mounted on the side. Lush greenery and a fenced yard are visible in the background.

Guesthouse in Sarasota

Private guest house in Sarasota!

Welcome to Casita Amarilla! Take it easy at this unique and quiet little studio getaway in Sarasota. 15 minutes from the famous Siesta Key Beach. Completely private fenced and gated yard including a driveway parking space. Perfect for 1 or 2 ppl with everything you need. Great neighborhood right near I-75 with a grocery store, walmart, pharmacy, hospital, gas station and several restaurants all within a 2 minute drive. We are the famous Christmas Light neighborhood as well. December is a treat!

4.97 out of 5 average rating, 137 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

Your family will love the oversized heated pool. Backyard/pool area is private from neighbors (kids be as loud as you want). BBQ & watch your favorite sports while the kiddos play in the pool. Enjoy gorgeous sunsets overlooking a peaceful park-like setting. Walk the golf cart paths, work on your tan, read a book, play your music, sip on a tropical drink & float all your cares away. Only a few miles from restaurants, bars, shopping & the excitement of Downtown Punta Gorda and Sunseeker resort.

5 out of 5 average rating, 10 reviews

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.

Home in Sarasota

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.

The living room features a comfortable beige sofa and a light-colored armchair, arranged around a wooden coffee table. A neutral area rug with a coral design covers the tiled floor. Natural light enters through a window dressed with light curtains, enhancing the tranquil ambiance.

4.99 out of 5 average rating, 73 reviews

Tranquil Destination Near Downtown & the Bay!

Situated in the Historic Cocoanut District, this neighborhood is diverse with an exciting vibe. Downtown Sarasota is walking distance away with the famous Ringling Museum of Art a short drive. The Coconut Places is one block from the beautiful Sarasota Bay. Coconut Hut is one of 4 suites that share a peaceful and serene courtyard. Perfect for working from, enjoying an outdoor meal, sitting around the fire pit, lounging in the sun or mingling with other guests.

4.99 out of 5 average rating, 326 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, 278 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 hot tub, pool

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...

4.92 out of 5 average rating, 131 reviews

A white gate opens to a well-maintained outdoor area, featuring a concrete patio with lounge chairs and a small table. Lush greenery surrounds the space, contributing to a serene outdoor setting. The pink exterior of the building is visible in the background.

Guesthouse in Sarasota

Have a great time

Your family will be close to everything when you stay at this centrally-located place. Lido beach is only 17 minutes away from the house. Siesta beach is only 19 minutes drive from the property. Downtown is a 6 minutes drive and a 34 minutes of walk. Beach chairs, cooler and beach umbrella available by request. Please let us know if needed and we leave it in house for your use.

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!

5 out of 5 average rating, 42 reviews

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.

Home in Sarasota

Waterfront Retreat | Heated Pool & Boat Dock

✨ Escape to this 3BR/2BA waterfront retreat on Phillippi Creek! Enjoy a heated pool, fresh modern décor, and a fully equipped open kitchen. Relax with 2 spacious living areas, each with Roku Smart TVs, plus a 50" Roku TV in the master. Essential bath amenities are included for your comfort. Perfect for families or groups seeking style, relaxation, and Sarasota charm.