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Madeira Beach, FL cottages
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12 Best cottages in Madeira Beach, FL

Guest-Favorite Family Cottages in Madeira Beach, FL

With plenty of room to spread out, these family-friendly cottages in Madeira Beach, FL are the perfect home base before a day by the water.

Beach Cottage - Renovated In 2025 & 30 Seconds To The Sand ! - Madeira Beach, FL
9.4 48 reviews

Beach Cottage - Renovated In 2025 & 30 Seconds To The Sand !

cottage, Madeira Beach
This charming cottage is conveniently located in Madeira Beach, just a short walk from the beautiful sandy shores and the lively atmosphere of John's Pass Village & Boardwalk. Guests consistently rate this property as excellent, highlighting its comfortable accommodations and prime location. This cozy vacation rental features one bedroom and one bathroom, comfortably sleeping up to three guests. Enjoy a refreshing dip in the private fenced pool, prepare meals in the fully equipped kitchen, and stay connected with complimentary Wi-Fi.
Updated Key West Style Cottage. - Madeira Beach, FL
9.8 11 reviews

Updated Key West Style Cottage.

cottage, Treasure Island
This charming beach cottage is located on the beach side of Gulf Blvd in Treasure Island, just steps from the white sand beach and within walking distance of restaurants, shops, and activities. It's rated excellent by previous guests and offers a quiet and peaceful setting away from the busy hotel areas.
The two-bedroom, one-bathroom cottage comfortably accommodates four guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, and parking. Enjoy easy access to a public boat ramp, the beach trolley, and nearby attractions like the Gulf Beaches Historical Museum, Imagine Museum, and John's Pass Village & Boardwalk.
Caribbean Vive Across The Gulf  Beach. - Madeira Beach, FL
10 34 reviews

Caribbean Vive Across The Gulf Beach.

cottage, Indian Rocks Beach
This charming cottage is located just a short walk from the beautiful beaches of Indian Rocks Beach, offering easy access to the area's attractions and a peaceful setting for a relaxing getaway. The cottage consistently receives excellent reviews from guests, highlighting its comfortable accommodations and convenient location.
The cottage features a modern design with an open layout, creating a bright and welcoming space. Guests can enjoy a range of amenities including a private garden, a shared patio with a BBQ grill, and access to a swimming pool and Jacuzzi.
2nd Story, High-n-dry, New Wifi. The Manatee. - Madeira Beach, FL
9.7 373 reviews

2nd Story, High-n-dry, New Wifi. The Manatee.

apartment, Madeira Beach
This Madeira Beach apartment is directly across from the white sands beach and within walking distance of John's Pass Village and the ROC park. It has excellent user, location, and cleanliness ratings.
The apartment has one bedroom, one bathroom, and a floor area of 330 square feet. It is newly renovated with new windows and leather furniture. It is fully furnished with a functional kitchen and has a private, high-speed 200mbps WiFi. The apartment also has a terrace/balcony, a garden, a swimming pool, a spa, and parking. Pets are allowed, and it is family-friendly.

Best Madeira Beach, FL cottages with a garden

Happy Hour Across The Street From The Beach - Madeira Beach, FL
10 11 reviews

Happy Hour Across The Street From The Beach

cottage, Treasure Island
This charming cottage is just a short walk from the beautiful beaches of St. Petersburg - Clearwater and the lively John's Pass Village & Boardwalk, offering easy access to both relaxation and entertainment. It has received excellent guest ratings, making it a popular choice for travelers.
The cottage has one bedroom and one bathroom, accommodating up to two guests, and features a fully equipped kitchen, a private garden, a terrace, a swimming pool, and free Wi-Fi. Enjoy modern amenities, including a Smart TV, a coffee maker, and a washer and dryer, along with access to a water park.
3 Mi To Beach: Seminole Retreat W/ Patio - Madeira Beach, FL
10 2 reviews

3 Mi To Beach: Seminole Retreat W/ Patio

cottage, Seminole
This cozy cottage is located in Seminole, Florida, just a short distance from both the Seminole City Center and Treasure Island Fun Center, offering easy access to shopping, dining, and entertainment. Guests consistently rate this property as excellent, making it a popular choice for travelers looking for a comfortable and convenient stay.
The cottage features a fully equipped kitchen with an oven, stovetop, and microwave, perfect for preparing meals. Enjoy the convenience of free self parking, free WiFi in public areas, and access to a marina for boat enthusiasts and water activities, as well as a patio and barbecue grills for outdoor relaxation.
Charming 3 Bedroom 2 Bath With Beach Access! - Madeira Beach, FL
10 4 reviews

Charming 3 Bedroom 2 Bath With Beach Access!

cottage, St. Pete Beach
This 3-bedroom, 2-bathroom condo is located in the Pass-a-Grille district of St. Pete Beach, offering proximity to St. Petersburg - Clearwater Beaches and John's Pass Village & Boardwalk.
This pet-friendly accommodation sleeps up to 7 guests and features air conditioning, heating, and is near opportunities for jet skiing, kayaking, and parasailing.
1 Bed 1ba Sunset Cottage Bungalow Treasure Island Gulf Beach Pool/boat/fish Dock - Madeira Beach, FL
10 1 review

1 Bed 1ba Sunset Cottage Bungalow Treasure Island Gulf Beach Pool/boat/fish Dock

cottage, Treasure Island
This intracoastal waterfront cottage in Treasure Island offers direct access to the Gulf beaches, is within walking distance of local shops and dining, and is less than 1 mile from John's Pass Fishing Village.
This 530 square foot, 1-bedroom, 1-bathroom bungalow accommodates up to 2 guests and features an equipped kitchen, air conditioning, internet, and access to a shared pool and outdoor spaces.

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Top Cottages with Jacuzzi in Madeira Beach, FL

A private hot tub at your cottage makes every trip to Madeira Beach, FL truly unforgettable after a day by the water.

Updated Key West Style Cottage. - Madeira Beach, FL
9.8 11 reviews

Updated Key West Style Cottage.

cottage, Treasure Island
This charming beach cottage is located on the beach side of Gulf Blvd in Treasure Island, just steps from the white sand beach and within walking distance of restaurants, shops, and activities. It's rated excellent by previous guests and offers a quiet and peaceful setting away from the busy hotel areas.
The two-bedroom, one-bathroom cottage comfortably accommodates four guests. It features a fully equipped kitchen, air conditioning, a Jacuzzi, and parking. Enjoy easy access to a public boat ramp, the beach trolley, and nearby attractions like the Gulf Beaches Historical Museum, Imagine Museum, and John's Pass Village & Boardwalk.

Choose the Right Dog-Friendly Cottages in Madeira Beach, FL

A quality pet-friendly cottage in Madeira Beach, FL offers dog-friendly facilities for a stress-free stay near the water.

`Oasis` Historic Beachside Cottage 3/2 - Madeira Beach, FL
10 1 review

`Oasis` Historic Beachside Cottage 3/2

cottage, Indian Rocks Beach
This waterfront cottage is located in Indian Rocks Beach, just a 2-minute walk to St. Petersburg-Clearwater Beach and 9 minutes from Splash Harbour Water Park.
This rental accommodates 8 guests and features 2 bathrooms, a full kitchen with a fridge and microwave, air conditioning, a terrace, garden, and on-site parking, with complimentary Wi-Fi and an in-unit washer and dryer.
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