Four newly decorated 2-bedroom pool cottages on Crescent Street, a 4-minute walk to the #1-rated beach in America.
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The Siesta Key Cottages are vibrant, festive, newly decorated 2 bed / 2 bath (sleeps 6) pool homes. They are within a 4-minute walk to the gorgeous Siesta Key beach access, with no major roads to cross. Point of Rocks, the closest beach access, is the most notable spot for sunbathing, paddleboarding, kayaking, snorkeling, and fishing, thanks to the amazing natural limestone formation that juts out across a shallow, soft-sanded bottom.
Private porches and seating in the lighted, lush, tropical landscape are available for those quiet moments everyone needs. You'll struggle with the decision to go down to the country's #1-rated beach, chill in the pool, or head to the Village, all within easy walking or biking distance. Rates as low as under $200/night, and everything is included.
The cottages have exclusive access to heated pools with a sun shelf. Inside you'll find beautiful new décor, flat-panel wall-mounted TVs in every bedroom and living area, plus Netflix, Roku, and Pandora entertainment. Fine linens, towels, and everything else here are truly first-class. Private washers and dryers and barbeque grills are available in each unit, and every cottage has its own toy closet filled with complimentary bicycles and beach equipment. Free private parking is included too.
Marc Wolff, the owner, is always a phone call away and happily willing to help you discover all that Siesta Key has to offer during your vacation. Everything you need for a wonderful experience is right here.
Each cottage has its own heated pool area, more private than the beach, with a full set of tables, chairs, and umbrellas. Relax, toss in some beach toys, and jump in.
Every unit comes with complimentary beach cruisers. Cruise all around Siesta Key on your own set of bikes.
All cottages include a fully loaded kitchen with stove, oven, spacious countertops, utensils, microwave, refrigerator, and freezer.
Parking on Siesta Key is tough, so we take care of it. With 15 spots for only 4 units, parking is never a problem.
Each unit has its own barbecue grill, and on chilly nights, don't forget about the fire pit.
Packed with nightlife, restaurants, boating, and the #1 beach in the nation. The free Siesta Key Trolley drives right by the cottages.
1109, 1111, 1115 & 1117 Crescent Street — each 2BR / 2BA, sleeps 6.
The villa's décor is beautifully done and truly festive, with colorful rooms and lively, bright cottage-style furnishings.
Whisk yourself away to a lovely tropical beach retreat in the cottage's modern, renewed styling.
Crystal-clear azure waters await your exploration. It's an amazing sight that holds endless days of fun.
Enjoy the heated pools, fire pit, and overarching palm trees. You're living like a local already.
Real photos of the cottages, pools, and grounds. Tap any photo to view it full size.
Powdery white quartz sand, sunset drum circles, the Village, and the Gulf at your doorstep. Tap any photo for details.
Consistently rated 5 stars by families, couples, and groups across Airbnb and VRBO.
"The host went above and beyond, with great communication and flexibility from check-in through check-out. The cottage was spotless and stocked with extras we've never gotten elsewhere: beach towels, a wagon, beach chairs, even a bag of ice waiting in the freezer. It's a short walk to Captain Curt's, the trolley stop and the beach, and the courtyard is full of games like putt putt, corn hole and badminton. If you're trying to decide between two places, this is the one to choose!"
Jenn · VRBO · Jun 2026
"The communication from Dave was excellent. The unit is completely redone with great bathrooms and kitchen, and one of the best things is all the outdoor space: a covered patio plus a private back area with a gas grill and fire pit. The beach is very close, just a five-minute walk to the beautiful Siesta Key sand. Would definitely stay again!"
Claire C. · VRBO · Apr 2026
"This place was CLEAN, not just surface level, it was spotless! Totally equipped with beach towels, bath towels, and cooking utensils. It has the perfect pool set up for kids with the sun shelf, and the beach was a nice short walk, 4 to 5 minutes with two toddlers in a wagon. We would love to rent several of the cottages together!"
Sara · Airbnb · Sep 2025
"We came with three other families so we had all four cottages. Check-in was extremely smooth, and they went above and beyond to get us in early. It was the perfect space to gather for family dinners each night. Would highly recommend, especially for multiple families. We will definitely return!"
Elizabeth · Airbnb · Apr 2025
"Spacious, well supplied and extremely clean, surrounding a landscaped courtyard with two small but inviting pools. Excellent communication throughout the stay. Short walk to Crescent Beach or a short drive to Turtle Beach with plenty of parking. Highly recommend."
Anita T. · VRBO · Jan 2024
"Plenty of room for our family of four and our dog, and we loved that there were no stairs. The courtyard was very pretty. It was a short, pleasant walk to Crescent Beach, our favorite in the area: beautiful, less crowded, and great for shelling. At low tide we reached Point of Rocks. Highly recommend!"
Heather · Airbnb · Jun 2025
"We rented the two cottages next to each other to celebrate my mom's 70th. The best part is the details: beach wagons, pool floats and beach toys, bikes, beach towels, even citronella candles for the patio. Each unit had its own patio furniture and felt private. We would love to come back!"
Alison M. · VRBO · Oct 2023
"A fantastic home. Responsive, friendly and always available. Even when we were affected by weather disruption and needed to stay an extra night, the hosts were accommodating and flexible. Perfect for a long weekend away with the comfort of home."
Cara · Airbnb · Jan 2026
"Perfect for our beach trip! Four couples shared two of the cottages very comfortably. Marc and Dave were so responsive, courteous and friendly, and the cottages were well stocked and clean. We will definitely book again!"
Jennifer W. · VRBO · Apr 2024
"We loved our stay! The location, house and communication were top tier. So cozy, comfy, clean and quiet, and a quick walk to the beach. The home had everything we needed and then some. We will be back!"
Kaleigh · Airbnb · Sep 2025
"The property was beautiful and the location perfect, walking distance to the beach. Super clean, and the pool and hot tub were really nice. Marc and Dave were great, and Dave was helpful, kind, and made our trip so much easier. We will definitely be going back!"
Diana C. · VRBO · Oct 2023
"The cottages were perfect for our stay. I loved that so many things, like beach items, were available for use. Communication was easy and Dave was very helpful. Can't wait to visit again."
Toni S. · VRBO · Jun 2026
"We absolutely loved this area and had the best time. We appreciated them providing bikes, chairs, beach access and games. It made our stay so enjoyable."
Lindsay · Airbnb · Jun 2025
"Just as advertised: clean and the perfect fit for our weekend. Quiet, comfortable, close to the beach. We took the trolley to Siesta Village for dinner and drinks. Property manager Dave was awesome and communication was great. We plan to stay again and highly recommend the Cottages."
Rob M. · VRBO · Aug 2023
"Great place. Great service. Beautiful beach. Had everything we needed, and Dave was very helpful."
Andrew · Airbnb · Jan 2026
Siesta Beach was again named the No. 1 beach in the U.S. by the 2025 Tripadvisor Travelers' Choice Awards.
WWSB ABC7 · May 2025Siesta Key Beach ranked No. 42 globally and was the only U.S. beach to make the world's top 50.
Sarasota Magazine · Feb 2025Tripadvisor's 2025 Best of the Best Beaches put Siesta Beach at the top of U.S. beaches and fourth worldwide.
USA TODAY · Sep 2024Crescent Beach was scientifically determined to have the world's finest, whitest sand.
Herald-Tribune · Feb 2024Siesta Beach was recognized as the top beach in Florida, the United States, and the world by Tripadvisor users.
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Siesta Key Cottages
