Smoking friendly holiday rentals 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.

Ocean View of AMI | Hot Tub | IMG | 6 TVs | 2 King

FREE Pool & Spa Heat Planning to stay a while? We love long getaways! Ask us about special discounts for stays of 14 nights or more — your extended vacation just got even sweeter! Your private slice of paradise in beautiful Bradenton, Florida! With breathtaking views of the inner coastal waterway, Longboat Key, and Anna Maria Island, this spacious retreat is the ultimate destination for families or groups looking for relaxation, adventure, and everything in between. **Spacious Comfort for Eve

Serenity Lake

Keep it simple at this peaceful and centrally-located place. 15 minutes from beaches this lovely apartment sits on a pond full of fish with a dock. Large pool ready for swimming and sunning. Charcoal and gas grill available. Beautiful upper deck to sit and enjoy the large mango tree and view over the lake. Golf cart available for evening rides. There is a large driveway for a boat. Swim and fishing accessories available. Minutes from I-75 - also near the famous Lakewood Ranch downtown.

Heated Pool, Hot Tub, Fire Pit + RV/Boat Parking

Relax and recharge at this private Port Charlotte retreat! Enjoy a heated pool, hot tub, fire pit— all in your own backyard oasis. The house sleeps 5, with a King En suite, Queen with pool view and office with daybed. Bring your RV or boat/trailer. Close to local beaches, golf, dining, and shopping, the perfect base for your Florida vacation. There is a separate garage studio that can be rented in addition to this property. It will not be rented otherwise when the main house has guests.

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.

Waterfront Suite-20 min to Gulf Beaches

A hidden gem awaits you in this waterfront “Old Florida” style guest suite. You’ll be in an attached yet private suite with your own entrance, bedroom & cozy living area. The setting offers amazing days swimming in the pool, kayaking or fishing. Maybe you’ll see manatees in the creek or the ducks, turtles, our cats & resident Blue Heron parade around the property. Beach lovers can get to Anna Maria Island in about 20 minutes. Nightlife? We’re 15 min from downtown Sarasota.

Pet Friendly 3 Bedroom Home, Fenced Yard

This 3 Bedroom Duplex is located near Lakewood Ranch, Parrish, and close to Sarasota. It is close to the Manatee River and near Fort Hamer Park, the Florida Railroad Museum, Lake Manatee State Park, Desoto Speedway, and Downtown Lakewood Ranch. We have renovated our home for maximum comfort with modern touches and with a fenced yard for children and pets. Our home is child and pet friendly. Ask if you need both sides of the duplex for 6 beds 2 baths total.

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.