Family-friendly holiday rentals in Madeira Beach

MadeiraC2 Waterfront & 2-3 minutes Walktothe Beach

Maderia Beach WATERFRONT & 2-3 minutes' walk to the beach. A great LOCIATION! A short drive from John's Pass Boardwalk & Johns' Pass Village. Feel the breeze, relaxing & enjoy the fishing on the docks right at our back yard! Everything you need, including 2 beds (1 Queen bed in bedroom & 1 twin sofa bed), well-equipped kitchen, parking permit, WIFI, Roku TVs, beach towels & chairs, umbrella. Restaurants, bars, shopping, Dolphin tours, fishing tours, boat & ski rentals ...are in walking distance.

Pearl of the Sea, 1 BDRM, 2 min walk to the beach

Please note, the gym, jacuzzi, and hot tub are temporarily closed(hurricane damage) Completely remodeled, beach theme decorated, a beautifully furnished second-floor condo just steps away from the white silky sandy beach! Ideal for romantic vacations, honeymoon escapes, and getaways! Located in Madeira Beach Yacht Club, a private gated community, free parking, high-speed WI-FI, TV cable, Netflix, 2 outdoor heated swimming pools, and fishing piers. Please, book at least 7 days before your arrival

“Beach Walk Retreat • Free Parking

Prepare to be swept off your feet by this stunning 2-bedroom apartment, situated just one block away from the beach. The perfect choice for families and couples alike, this property offers a fantastic opportunity to soak up the sun. Take a 5-minute stroll down to the beach and indulge in a relaxing day of beachcombing, building sand castles or taking a dip in the ocean. Take a break from the sand and head back to your tranquil haven, where you can cook up a delicious meal at the backyard grill

40ft Floating Bungalow with Resort Perks

Unmatched Scenic Serenity: Imagine waking up to stunning sunrises and gentle ocean breezes. Your houseboat becomes a floating oasis, providing the comforts of a hotel but floating. Exclusive access to the resort across the street on the beach. Where you can use the heated pool and hot tub. Outdoor grilling area with corn hole boards are available to entertain you while you cook at the Beach Resort. No Grill on the Boat. *Boat is stationary at dock. **MOTION SICKNESS?? PLEASE DO NOT BOOK**

Coastal Retreat Madeira Beach/John’s Pass Pool

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Step into coastal style at this Madeira Beach condo with Gulf views. Designed with a beach-inspired theme, this retreat offers a breezy open layout, fully equipped kitchen, and balcony perfect for soaking in sunsets. With resort-style amenities on site and dining, shopping, and entertainment nearby, it’s an ideal escape that blends a laid-back coastal vibe with the convenience of a prime location.

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.

Private Guest Suite 2 miles from Beach

Private, small completely renovated Guest Suite with Private parking, private separate entrance with deck. Space is best for 1-2 people: small, but thought out. 2 miles from Treasure Island beach. 2.5 miles from the St Pete beach! Beautiful quaint neighborhood. Near great fishing spot Kitchenette Full Bathroom Comfy queen size bed Cool AC unit ❗️WE HAVE GREAT REVIEWS, but please view before booking “Is this guest suite right for you” below under “things to note” to have the trip you desire

Experience the charm of Gulf Gardens. The Pelican.

Come visit the gem of Madeira Beach, and discover the charm that has visitors coming back for decades. Enjoy a quiet, clean tropical old Florida feel that's hard to find anywhere in this sought after beach community. This property features lush landscaping and one of the largest, cleanest pools you'll find. Our visitors appreciate the attention to detail the owners put into making Gulf Gardens a special place they want to visit year after year. The white sands of Madeira Beach are calling.

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.

1Q Pet Friendly Island Studio / Heated Pool Access

*Must be 21(Unit is across the street from the beach. There is not a beach view from this unit. Resort Amenities are just across the street.). *1 Pet Max $50.00 Clean Simple Unit Nothing Fancy . Stainless Full size refrigerator , TV, Microwave, Coffee Maker, Iron and Board & Hair Dryer Just steps from the beach with access to resort Amenities including heated pool, hot tub and lagoon pool.Coin operated Washer/ Dryer and Outdoor Grilling Area available. Unit is ground floor.

Cozy Gem Near Madeira Beach With Private Patio

This cozy studio unit with its own screened-in large private patio is the perfect getaway for up to 2 people looking to enjoy the beautiful beaches of this area. Located in a quiet neighborhood on a private cal-de-sac, it is the perfect place to rest and recharge between trips to the most beautiful beaches in the world. This location is just a quick 5-minute drive (2 miles) to the Madeira Beach access and a 10-minute drive to the famous John's Pass Village and Boardwalk.

Lux Condo w/ 2 balconies, Ocean & Marina views

This luxury condo features 2 private balconies, w/ spectacular ocean & marina views. It's stylish decor, meticulously picked quality & comfortable furnishing/accessories are sure to please. It’s conveniently located just across the street from the pristine white sands and sunsets of the Gulf of Mexico. It is adjacent to the #1 tourist destination in the county, John's Pass Village. The property offers a heated swimming pool, hot tub, fitness room & event center.