Cottage holiday rentals in Sarasota County

Chic Peaceful 3BD Cottage - Walk to Siesta!

Welcome to the Key Lime Surf Shack, a bright and stylish 3-bedroom cottage just minutes from world-famous Siesta Key Beach. Perfect for families, couples, or small groups, the home features a king and queen bedroom plus a flex room with a daybed, an open living area with Smart TV, a fully stocked kitchen, and in-unit laundry. Relax in the spacious shared backyard with tropical landscaping, or head out to explore Sarasota’s best dining, shopping, and outdoor activities nearby. Designed with comfo

Historic Cocoanut Art Cottage

THE COCOANUT ART COTTAGE Located three minutes to downtown! The Cocoanut Art cottage is a restored 1940s two-bedroom, one-bath house with hardwood floors, a fully-equipped kitchen and dining area, living room and outdoor space. Shiplap walls throughout the home are filled with art by Ringling School of Art alumni including Joseph Patrick Arnegger, Tom Stephens, Tim Jaeger and many more. The space is furnished with comfort and style by a local interior architect, a Ringling alumni. VR24-00168

Quaint Cottage,150 steps away from Crescent Beach!

Nestled on the serene Crescent Street, this classic 1969 cottage, is just a short walk to the ground quartz sands of Siesta Key. The 500 sq foot private brick paver and stone backyard off the screened in lanai is fully fenced with custom built stainless outdoor kitchen, featuring a large grill, refrigerator, custom built stone bar with seating for 8 . Nearby is a blue glass gas fire pit with a seating area, over sized (9 ft. diameter) in ground "spool", loungers and a large circular daybed.

The Mermaid: Heated Pool, 4 Houses to Beach

This apartment is a first-floor unit with an open floor plan that sleeps 2 with a maximum of 4 people. The bed makeup in this rental is a king bed in the master and a queen size sofa sleeper. This rental is great for longer stays or guests who like to cook since you have a full kitchen and all the items to cook any meal. There is a washer/dryer in the apartment. Beach chairs and umbrellas are supplied to you at no charge. This is a duplex and has another 1 bedroom 1 bath apartment above you.

Cozy Cottage by the Bay

Charming and historic decorator cottage near Downtown Sarasota. Located in the highly desirable, quiet, and safe neighborhood of Indian Beach - Sapphire Shores. Just a short drive to some of the nations top rated beaches like Siesta Key Beach. One of the best features of the home is the enclosed lanai at the front of the house. Perfect for enjoying Florida's coveted indoor/outdoor living. It has a private fenced in backyard, with a fire pit. Off street parking for 2 cars in the driveway.

Siesta Key Cottages Crescent 1B Beach/Pool/Hot Tub

4 separate BRAND NEW inside (renovated 12/24) 2 bedroom/2 bath (+Queen Sofa Bed+ Chair/Bed) pool homes (Each sleeps 7) ONLY A 4 MINUTE WALK TO SIESTA KEY BEACH #1 in USA (no major streets to cross): First Class! 2 Heated Pools, 2 hot tubs,2 gyms, Smart TV’s in all rooms, fine linens, towels, bikes, beach equipment, private porch, grill, fire pit, outdoor shower, private parking: Great restaurants / nightlife in walking distance. Running/Walking: You have miles of beach to take in!

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

*Siesta Key elevated villa at Solitude Suites on Siesta Key. *Your own detached private villa, located in a small resort. *Waterfront resort w/ heated pool, kayaks, table tennis & Tiki Hut. * Just a 10-12 min walk to award winning beach. *1 Bedroom w/King bed. *1 full bathroom w/shower. *Large kitchen, open living room, fully furnished inc towels & linens. *Private lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Adorable Cozy Silver Sands Cottage on Siesta Key!!

Adorable one bedroom "Old Florida Cottage" on the intracoastal bay side of Siesta Key. This is a stand alone cottage, ground floor, no elevators or flights of stairs to mess with. New Pool with a tiki hut, fishing dock, boat basin (up to 24'), beach access 4 min. walk across Midnight Pass Rd. to the #1 beach with the whitest, softest sand you'll ever see! Hi Def TV in LR , Wifi, TV in BR, Keurig in the kitchen, stocked with everything but your clothes and toothbrush.

Magnolia Cottage

Enjoy the walking-distance restaurants, shops and bars from this cozy cottage in the heart of Olde Englewood. Catch fish or the sun dancing on the water at Lemon Bay just two blocks away. The neighborhood is great for morning and evening strolls. Four local beaches are just minutes away. Relax with a refreshing beverage on the back patio, fenced for your privacy. If you want to park the car and enjoy a quaint beach town without the hassle, we have you covered!

Staycation Sanctuary

Our property is clean and welcoming. You can enjoy a relaxing, warm and peaceful getaway from the rest of the world just steps to the beach. This is the perfect "Old Florida-style" location to experience the comfort and hospitality you so deserve! Grab your bathing suit/flip flops and enjoy tranquillity of beach life, sunsets and lazy days of fishing and bird/dolphin/manatee watching and gathering sea shells-- all only 2 blocks away!

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Casita Verde blends classic vintage charm with modern comforts. This 2-bedroom, 1-bath home features a 55" flat-screen TV with HD cable and fast Wi-Fi. Relax by the private pool or enjoy peaceful evenings on the deck with your favorite drink. Pet-friendly and conveniently located near Downtown Sarasota on Bahia Vista, with an easy drive to Lido Key, world-famous Siesta Key, and I-75 for day trips and longer adventures. 🌴

Bamboo Cottage, minutes to beach, no guest fee!

We pay Airbnb's Guest Fee. Save on Weekly and Monthly Stays! Discount automatically applies :). Welcome to The Bamboo Cottage! A peaceful and private 1940's Old Florida farmhouse tucked away in Englewood's Historical District. Centrally located within walking distance to Dearborn Street & Lemon Bay, and just miles to the beautiful beaches of Manasota Key!