Smoking friendly holiday rentals in Sarasota County

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

Golf Cove in Paradise ☀️ A private peaceful resort style outdoor space + 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. Gorgeous sunsets overlooking a golf course setting. Enjoy your coffee outside & hear the birds sing. Carefree outdoor living is what it’s all about here.

Nottingham Beach Bungalow Near Siesta Key Beach

Book your Summer 2026 getaway - 30% off stays of 28+ nights. Pet-friendly Nottingham Beach Bungalow near the #1 rated - Siesta Key Beach, downtown, Trader Joe’s, restaurants & SRQ. Enjoy a remodeled bath, stocked kitchen, T-Mobile 5G Wi-Fi, smart-lock self check-in, beach gear, assigned parking for 2 cars, private front-yard dining table & umbrella w/ seating for 4, & a charcoal grill. The shared fenced backyard w/ fire pit & propane grill. Best for 2; sleeps up to 4 to 6 with sleeper sofas.

Getaway Near Lido Key, 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.

Indigo at the Beach 21!

Venice area open and ready for your stay! High end Saltwater Pool and Spa with a beach feel with awesome beds and Smart TVs to watch NFL Ticket or movies. High ceilings and doorways with a comfortable coastal theme to "chill out" and relax on the island. Location is 3 blocks from the Beach & charming downtown Venice for dining, coffee, shopping, pickleball & farmers mkt. Located across from a Park with walking trails. Beach gear/cart complimentary. Golf cart (6) available for rent.

Elegant heated pool canal home in very quiet area.

Great location! Bring your dog, bring your boat and enjoy the Florida sun in your heated saltwater swimming pool. Fish off your private dock while watching for dolphins or manatee. You can meet the rest of the opacarophiles who walk to the beach to view the sunset. Relax in the jacuzzi with your favorite beverage. NOTE: Beach is sandy but the water is BRACKISH, not clear. This is mostly a retirement neighborhood. This is NOT a party house and not suitable for unattended children.

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.

Welcome to "Casa Amarilla"

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

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.

The Roaring Palm

Book your stay at this, charming, sun-filled house just 5 min from downtown and 10 min to the beach. Enjoy your morning coffee in a private outdoor nook, stroll Gillespie Park across the street, and relax in two cozy bedrooms with TVs. Clean, spacious, and fully stocked for a comfortable stay—with two off-street parking spots and all the essentials for a perfect Sarasota escape. Pets allowed, max 2 pets.

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!