Holiday rentals with a patio in Osprey

5 out of 5 average rating, 14 reviews

Cottage in Sarasota

Beach Cottage Siesta Key Prime Location & Htd Pool

Newly Renov. Beach Cottage on World Famous Siesta Key Beach in the heart of it all. Incl.1 parking space. Walk everywhere. Great Dining, entertainment, shopping, bike rentals and more, across the street or take FreeTrolley to Siesta Key Village. Located on the Beach Side (2min.walk to waters edge) with Heated Pool. Best Location on the Island! Private large outdoor Patio w/outdoor shower. In Unit Washer/Dryer. Free Luxury Amenities. Highly sought after 1 bd 1ba. Book your stay in advance!

4.84 out of 5 average rating, 19 reviews

Home in Englewood

Sunset Getaway

Beautiful cottage,conveniently located only minutes from pristine Englewood beach.Relax and take a nap on the hammock,sit by the fire pit,fire up the gas grill,relax in the screened-in lanai or enjoy the privacy of the fenced- in backyard.When you're done soaking in the sun and swimming in the calm, clear waters you can walk across the street to the awesome outdoor/indoor restaurants & bars with live music located steps away & enjoy the gorgeous sunset. Live the Florida lifestyle in paradise.

4.96 out of 5 average rating, 122 reviews

The Bradford Cottage/Heated Pool /Mins to Siesta

If you are looking for a cozy retreat in a safe and private neighborhood than look no further! From the minute you step inside this immaculate private residence you will feel right at home. With a beautiful open floor plan with plenty of room to spread out, natural light that pours in every room and a spacious back porch overlooking the heated pool this is the perfect place to unwind and relax. Minutes from the #1 rated Siesta Key beach and downtown Sarasota you are in the middle of it all!

5 out of 5 average rating, 9 reviews

Guest house in Bradenton

Serenity Lake Too!

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.

4.85 out of 5 average rating, 20 reviews

Flat in Sarasota

Siesta Key Palm Bay Club Newly Renovated Must See

Siesta Key Beach new renovation at The Palm Bay Club Enjoy sunrise to sunset from our great resort that has private bay to beach access . 2 bedroom 2 Bath ground floor with walk out balcony .Each bedroom offers private en-suite, Clean and bright open floor plan, well appointed kitchen ,Central A/C . Resort features 2 heated pools , enjoy the tranquility of the bay from the large hot tub or pool . Fishing pier, tennis & pickle ball courts, gym, laundry area we also offer boat slips

4.95 out of 5 average rating, 19 reviews

Warm, Luxury Oasis in Central Sarasota

Choose to stay at a home which has it all. Professionally designed and hosted by a 10-year SuperHost, this property offers incredible value. Superbly comfortable beds and linens, SUPER FAST internet, thoughtful furnishings, tons of activities & games, fully equipped for babies and toddler needs, extremely central location, large, high-end TVs, a jacuzzi, 2-person hammock, in-ground fire pit…. And fur babies welcome… you name it, this home has it. Welcome to Sarasota Paradise.

Superhost

4.75 out of 5 average rating, 4 reviews

Amazing Location! Amazing Amenities!

This is a weekly rental with a 7 day minimum. No smoking permitted! Top-rated vacation resort is in the perfect location - not only within the resort (close to the entrance and amenities), but also for Sarasota! 20 min from the airport, 15 min from the beach, 5 min from incredible shopping and across the street from Cooper’s Hawk! SunOutdoors Sarasota is an award-winning vacation resort with indoor & outdoor pool, fitness center, mini golf, pickle ball - you name it!

Flat in Indian Beach-Sapphire Shores

4.96 out of 5 average rating, 131 reviews

Free Early Chk-in, Super Clean, Parking, Disney+.

Escape the ordinary and immerse yourself in an extraordinary stay at our unique Airbnb property on the main road 1 mile from downtown Sarasota. Discover over 60 enticing amenities, from a secure room safe to a luxurious, indulgent bed. Just a stone's throw away from downtown Sarasota, Lido Beach, and essential amenities like grocery stores and pharmacies, our corner apartment with a dazzling wrap-around patio is your perfect hideaway. Bicycles at your disposal. Book now

5 out of 5 average rating, 15 reviews

Home in Punta Gorda

Harbor View Sunsets Historic Downtown Charm

Expansive direct Harbor-front views across the street from Gilchrist Park in the heart Punta Gorda’s Downtown Historic District. Short walk to local attractions, Harbor Walk, Fisherman’s Village, TT’s Tiki Hut Laishley Crab House, Sunseeker Resort, Farmer’s Market, Art Museum, Downtown Dining, & Shopping. This is by far the best location to stay in Punta Gorda, you will not be disappointed! This home can sleep up to 8 guests but no more than 6 adults comfortably.

4.95 out of 5 average rating, 39 reviews

Sarasota Coastal Cottage

This 2-bed, 2-bath gem features an open floor plan, exquisite bathrooms, a cozy den/office, and a stunning backyard patio, crowned by a majestic oak—perfect for al fresco dining. Nestled in Paver Park, you are a stroll away from Payne Park & Legacy Trail and just minutes from Downtown, Bayfront Park, Selby Gardens, St Armand's Circle and beautiful Lido & Siesta Key beaches. Experience Sarasota in true style. Per city ordinance a 7 night/day minimum booking required.

Superhost

Campervan/Motorhome in Port Charlotte

4.8 out of 5 average rating, 5 reviews

Entire Rv with BBQ and Patio.

Escape to a charming and comfortable RV getaway, perfect for a relaxing retreat! This cozy RV is fully equipped with all the essentials, offering a unique stay with modern comforts. Step outside to enjoy your private patio, complete with a BBQ grill—ideal for outdoor cooking and unwinding under the stars. Located in a peaceful setting, this space is great for solo travelers, couples, or small families looking to experience the outdoors with a touch of home.