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.

XL Pool~Private Yard~Striking Sunsets~Outdoor tv

Welcome to Villa del Sol ☀️ A peaceful resort style outdoor space + private + oversized solar heated pool creates a perfect vacation oasis. Covered lanai = shade. BBQ & watch your favorite sports on 55” outdoor tv. Walk the golf cart paths, swim laps, get a tan, read a book, play music & games, sip on tropical drinks & float all your cares away. Pretty sunsets overlooking a serene park-like setting. A.M. coffee outside to hear the birds sing. Carefree outdoor living is what it’s all about here.

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 character, high-speed Wi-Fi, games, TV and a peaceful garden. Near Sarasota Bay, Ringling Museum of Art, Siesta & Lido Key Beach, Mini Golf, nature and culture at your doorstep. Superhost Status Special Rate Happening Now! SRQ Registered Vaca #VR25-00145

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!

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.

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!

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! 🦩

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!

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! 🌴🏖️