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Waterfront Escape•PingPong•Relax & Recharge•Pool

Your peaceful waterfront escape awaits. This cozy 2BR/2BA cottage offers two living areas. The bright Florida room overlooks the canal. It includes areas for a game of ping pong, a life‑size Jenga set, watching tv, having a bite at the table, and a sleeper sofa. Enjoy morning coffee at the dock watching the fish jump or grab your pole. Relax by the sunny pool or practice on the putting green ⛳. Fast WiFi, a dedicated workspace, beach gear, and a full kitchen make winter stays easy and relaxing.

The Magical Mermaid Cottage

Historic Vintage Cottage ideal for Nature Lovers Step back in time at our 1920s pet-free cottage, nestled in a quiet historic neighborhood near the Riverwalk, Anna Maria Island beaches, and Historic downtown. Renovated in 2019, it blends vintage charm with rustic touches from our family farm in Iowa. Surrounded by native greenery and tucked behind our pink bungalow, it’s a peaceful haven for those who love all that nature offers, history, simple living, good people, and whimsical mermaid vibes.

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."

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.

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.

Cortez ~ Grouper Cottage. BRING YOUR BOAT!

This waterfront home with private dock and boat slip is the perfect place to get away. Grouper Cottage is an ideal cozy place to unwind and enjoy sunsets and dolphins. You will fall in love with this refurbished historic cottage. Private setting offering tranquility, with picturesque palm trees and mangroves surrounding the property's shoreline. Cortez dockside cottages is nestled on an acre with a compromise of old Florida with the historical background a laid back Island vibe.

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!

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!

Ohana Gulfside C Historic 1 Bed - 250 ft. to Beach

COMPLETELY REMODELED! Aloha and welcome to our bit of old Florida. Ohana Hale Gulfside is 250 feet to the white sand beaches and turquoise water. Come join us for your vacation in the sun. The ideal bungalow for a couple or small family. This one bedroom, one bath with kitchenette is made for your best vacation memories. This unit is only one block to the beach and one block to the Bridge Street shopping district and the pier! This unit is one-pet friendly.