Cottage holiday rentals in Madeira Beach

Vintage Florida Beach Cottage B

Just a short walk to the beach makes this a great beach getaway for couples or families. On your way you can stop at the Kooky Koconut for lunch, an awesome milkshake or a variety of snacks. With a totally new renovation in 2019, this unit is in updated, very clean and worry free condition. This cottage is located in a quiet residential neighborhood and a great place to relax. Common laundry on shared screened porch. Dogs allowed (extra $45 cleaning). Easy refund policy. Level 2 EV charger

Pass-a-Grille Historic Cottage Unit 1

PASS-A-GRILLE HISTORIC COTTAGE UNIT 1 A fully renovated historic beach cottage located in beautiful Pass a Grille, Florida. Steps from the Gulf of Mexico and Boca Ciega Bay. This is a duplex; Unit 1 - 1 bedroom/1 bath. Household linens, towels, cookware & dishes provided. Appliances include; dishwasher, washer/dryer, flat screen TVs and wi-fi. Vintage-style tiled bathroom and shower. High end window shades on all windows. Front patio area w/ BBQ grill. Private parking for 1vehicle on premises.

Family Friendly Beach Cottage in Madeira Beach, FL

Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

Luxury Beach Bungalow | Walk to Dining & Sunset

Escape to paradise at Sunshine Escapes! Welcome to #CocoPalmsIRB, nestled in the heart of Indian Rocks Beach. IRB is a hidden gem that radiates a whimsical, small-town charm, evoking nostalgic memories of carefree childhood summers by the shore. The Gulf of Mexico beckons just two blocks away, offering pristine fluffy sands and unforgettable sunsets. As the sister cottage of Mango, #CocoPalmsIRB invites you to immerse yourself in the laid-back beachy vibes of IRB. Your perfect getaway awaits!

2 bed/1 bath Hummingbird Beach Cottage (4 beds)

This is a 1951 beach bungalow with all the updates, including a walk-in shower, on-demand hot water, and stainless steel appliances. Comfortable, clean, and cozy. Two queen beds and two full sofa sleepers! The beach is just a short walk across Gulf Blvd and views of million-dollar homes, piers, and sunsets to die for! Great shell collecting. Fantastic location with lots to walk to. Groceries, Dollar store, bars, restaurants, and coffee are all walkable. Just under two miles to John's Pass.

#5 Beach Front Cottage w view- Indian Rocks Beach

LOCATION, location! Closest beach cottage to the water at Indian Rocks beach, view of the water from your porch & easy access to grass for pets. Perfect couples getaway. Enjoy some of Florida’s best beaches. Minimalistic living. *Kitchen recently updated* Shared gazebo & picnic table next door. Shared Washer & dryer takes quarters. Walking distance to local restaurants and bars. Minutes away from Clearwater beach, tourist attractions and mini golf. Property located next 2 public access.

Beautiful Beachfront Cottage on the Water

Renovated, romantic 1937 beach front cottage. Last of its kind in the quiet family setting of Indian Shores Florida, halfway between Clearwater Beach and Treasure Island/John's Pass. Truly an "Old Florida" experience with original pine floors, Florida room and covered porches, as well as updated kitchen and bathroom. This house, uniquely built near ground level, allows it to be waterfront on the beach while shaded by huge pine trees. You won't find a more tranquil setting on the beach.

Kooky Coconut Cottage, Indian Rocks Beach

Coconut Cottage only steps away from the beautiful beaches of Indian Rocks Beach. 2 bedroom,1 bath. The entire cottage has been renovated. Next door to the local famous Kooky Coconut Cafe. Perfect for couple, friends or small families. ONLY 3 GUESTS ALLOWED. NO sleeping on the sofa ALLOWED. If you bring more then 3 guests you will be charged $100.00 surcharge per night per extra guest. Due to cleaning restriction we DO NOT allow cooking with CURRY or FISH OIL in the cottage.

Historic Holly House on Treasure Island

This charming Beach Cottage is located in the Coney Island area of Treasure Island. This unique set of Key West Style beach cottages are on the beach block only STEPS to the beach! This awesome beach cottage, known as The Historic Holly House, has some unique history. In 1961 the New York Yankees rented out all the cottages in this Coney Island area for spring training. This cottage was the one the Home Run King Roger Maris stayed in before he went on to hit 61 home runs that season.

New Beach Retreat– Hammock, Patio & Steps to Sand.

Sandy Feet Cottage is a newly remodeled beach retreat just 2 minutes from Indian Rocks Beach. Enjoy an open layout, new furnishings, a spa-style bath, and a private yard with fire pit, hammock, and patio. Walk to dining, bars, and shops—your stylish Gulf Coast escape. ***NEW AIRBNB PRICING UPDATE*** Starting mid-October 2025, Airbnb will display all-in pricing—including a 15.5% Airbnb service fee (charged directly by Airbnb to the host), plus cleaning and pet fees if applicable.!

*GROUND FLOOR DIRECT BEACHFRONT COTTAGE!!*

Step out the door and into the sand! Ground floor DIRECT beachfront one- bedroom/one-bath cottage nestled in the sand directly on the Gulf of Mexico with awesome amenities for the perfect Gulf Beach getaway! Enjoy a cozy bedroom, living/dining area, fully-equipped kitchen, beachfront patio and private beach area with lounge chairs. Conveniently located near a trolley stop for easy access to local restaurants, shops, and attractions. Book now for an unforgettable beach vacation!l

Adorable Cottage, Pet friendly, near beach & DT

The Cottage is a beautiful, comfy, clean, peaceful home where you will feel just at home, in the hearth of St Pete. It is in a great location, safe & quiet neighborhood, easy-to-access, just a short drive or bike ride away (5-10 minutes) to many good restaurants, grocery stores, museums, library, coffee place, breweries, hospitals, bars and night clubs in downtown & sandy white beaches. Jumped in the sun runner or public transport to downtown or beaches. Perfect for long stay.