Smoking friendly holiday rentals in Sarasota

Bayou Hammock, Sarasota FL

Welcome to Bayou Hammock, your private Sarasota retreat. Enjoy an open-concept layout with a full kitchen, serene bedroom, and amenity+ necessity galore. Utilize the spacious deck surrounded by a hammock of oak under the umbrella. With modern features, high-speed Wi-Fi, games, TV and a peaceful garden path, it's perfect for any escape. Near Sarasota Bay, Ringling Museum of Art, Siesta & Lido Key Beach, Mini Golf - nature and culture at the doorstep. Sarasota Registered Vacation Rental VR25-00145

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.

~ 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.

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,

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.

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.

Tipsy Flamingo | POOL • HOT TUB • FIRE PIT • GAMES

Dive into the curious home of Tipsy Flamingo. The tropical fever dream you didn’t know you needed! Stay in a historic home bursting with fluorescent colors, a pink-tastic Flamingo Suite, a wild Jungle Room, and a chill coastal Surf Den. Outside, swing under the pergola, battle it out in giant chess, soak in the hot tub, lounge by the fire pit, and float in the sparkling pool on your honorary pink flamingo throne. Pure fun, pure vibes, pure madness! 🦩

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.

Backyard Breakaway

New house, experienced host. Book now, your private oasis in the heart of Sarasota. This bright, airy home opens to a massive backyard made for memories—grill under the stars, dine under the gazebo, unwind by the fire pit. Inside, enjoy an open layout, two cozy bedrooms, and a charming coffee station. Just minutes from downtown and the beach, with plenty of parking. Everything you need to relax, recharge, and feel at home.

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...

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!

Bay | Free Pool Heat | Private Backyard | Game Roo

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! 🌴🏖️