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.

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.

A slice of paradise!

The guest cottage (approx. 300 sq ft) is separate from the main house, where we reside, with a beautiful saltwater pool to cool off in after your day's adventures! The property is 5 blocks from downtown Gulfport, with waterfront restaurants, bars, arts district, unique shopping, and beach. Close access to new tennis courts, bayside beach and minutes away from modern downtown St. Petersburg, and world-famous beaches. We are not set up to host pets or children and no unaccounted for guests.

Olympic Oasis | GYM • POOL • GAMES • BBQ • GAINS

Welcome to Olympic Oasis, your tropical training ground meets resort-style getaway. Start with a gym sesh in your private gym, then reward yourself with a cooling dip in the sparkling pool. Sink into chic loungers or relax in serene spaces crafted for total tranquility. Feeling playful? The arcade awaits. Feeling photogenic? We’ve got the perfect backdrops. All this sits in Bradenton’s prime location, close to pristine beaches & the best hot spots. Work hard. Play harder. Vacation hardest.

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 Yard~Peaceful Location

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.

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.

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.

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...

Grotto Pool Retreat | 3BR Home Near IMG & Beaches

Unwind at The Grotto Pool House — a 3BR, 2BA Spanish-style retreat less than 5 miles from IMG Academy, Anna Maria Island & Downtown Bradenton. Enjoy a private grotto-style pool, fast WiFi, Smart TVs, and a fully stocked kitchen. Pet friendly (max 2 dogs, fee applies) with washer/dryer and essentials for extended stays. Locally cohosted by HomeIngo for a true 5-star Florida experience.

Chef’s Dream Kitchen | Hammock | Htd Private Pool

✨ Welcome to The Bay 218 — a stylish Sarasota retreat just steps from the bay and minutes to Lido, Siesta Key, Longboat Key & AMI. Enjoy a chef’s kitchen, two living areas, luxe primary suite, kid-friendly bunk room, and a private heated pool with tanning ledge, lights & basketball hoop. Beach gear included, dog-friendly, and perfect for both short stays and 14+ night discounts!