Cottage holiday rentals in Casey Key, Florida

Ty's Canal Cottage

"Welcome to Ty's Cottage in Historic Cortez Fishing Village, which is one of Florida's last working fishing villages. Located within walking distance to well known Starfish, Swordfish, Tide Tables Restaurants and Tyler's Homemade ice cream. A short 1.3 mile walk to Anna Maria Island with gorgeous beaches. Short driving distance to beautiful golf courses such as IMG Academy Golf and Manatee County Golf Course. Local fishing charters for outstanding fishing. Outdoor sitting area on canal."

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.

Unit #1 Free kayak/bikes/walk to beach/fullcottage

Unit #1 Beach cottage very private and quiet, has a full kitchen, King bed in the master and queen sofa bed in the tv room, very comfortable, fast WiFi, AC & heat. All you need to relax and just have fun. Outdoor shower and laundry area, Private parking, Enjoy amazing sunsets/fishing/and restaurants and bars, all walking distance to the beach and bay. Kayaks/snorkel gear/beach toys are included. So start enjoying the beautiful sandy beach on Manasota Key, Lots of sea life and turtles.

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.

Bradenton Beach Sunsets 3, Anna Maria Island, FL

Fully furnished water view beach cottage located on beautiful Anna Maria Island across the street from white sand beach and Gulf of Mexico. 1 Bedroom 1 bath unit that sleeps 4 with a queen pull out couch make this a great location for, solo guest, business travelers, and families. . Beach chairs/umbrellas/etc. provided. 3 blocks from historic Bridge Street with lively restaurants and bars. Free island trolley and across the bridge from Cortez fishing village. Free off-street parking.

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/ FREE 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 screened lanai w/ table & chairs. *Beautiful shared pool w/ sun shelf & waterfall. *2 min car ride to beach. *Updated!

Private Heated Pool Casita Near Downtown & Beaches

Built in 1925, Our Casaita Verde 2 Bedroom, 1 Bath home still retains its vintage charm but with modern touches. Enjoy watching the 55 inch flat screen TV with HD cable and stay in touch with the world with WI-FI internet. Lounge by the private pool or take in the beautiful evenings on the deck with your favorite beverage. Pet Friendly! Conveniently located near Downtown Sarasota on Bahia Vista with easy drive to Lido Key, our World Famous Siesta Key or I-75 for longer adventures.

Coastal Style 2BR cottage near Anna Maria Island

Relax with the whole family at this peaceful place to stay. Located in a mobile home/RV park 6.5 miles from Anna Maria Island, which offers some of the most beautiful beaches on the gulf coast. Centrally located between St. Petersburg and Siesta Key. This kid friendly community offers many amenities such as Pickle ball, swimming pool, shuffle board, horseshoes and gym on site. Stay a few days or a few months! Snow birds are welcome! Only 3.3 miles to Sarasota Airport.

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.

Darling Old Florida Beach Cottage Steps From Gulf!

Fully Renovated Coastal Gem! Welcome to Cottage By The Sea — a beautifully updated retreat just steps from the sugar-white sands and turquoise waters of the Gulf of Mexico on Anna Maria Island. Tucked away in the peaceful community of Bradenton Beach, this charming escape is one of the few remaining “Old Florida” cottages, lovingly restored with modern touches and cheerful, sun-filled décor. Leave your worries behind and unwind in your own slice of island paradise!

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!

One Block to Beach - Ohana Hale Beachside 2 BR

COMPLETELY REMODELED February 2025! Aloha and welcome to our Island Home Ohana Hale AMI! Our home is designed for the ultimate beach vacation experience, featuring 2 cozy bedrooms and 1.5 baths. The open kitchen and living area create a spacious, inviting atmosphere, perfect for relaxation and fun. Be sure to check out our amazing 3rd-floor shared deck—it's the perfect place to watch stunning sunsets over the Gulf of Mexico.