Family-friendly holiday rentals in Madeira Beach

4.94 out of 5 average rating, 176 reviews

Stunning Views Beach Front Condo

Beautifully updated 4th floor 3 bedroom beach front condo! Enjoy gorgeous views of the Gulf of Mexico from a large screened in balcony! Gulf view from both the living room and master bedroom. A large updated kitchen is perfect for the whole family. This condo sleeps 6 comfortably. Cable and WIFI are available as well as beach necessities. A view of the Bay from the front door. Walking distance to John’s Pass. Due to the hurricane, there is still minor repairs being done around the building/town.

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4.95 out of 5 average rating, 111 reviews

Beach Front at “The Shore”

Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

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A comfortable living area features a round dining table set for four, surrounded by modern chairs. Two seating areas include plush armchairs and a sofa, complemented by a tropical plant. Large windows offer natural light and views of the outdoor scenery.

4.97 out of 5 average rating, 102 reviews

Penthouse Condo on Water Steps to Beach+Johns Pass

Escape to paradise at our gorgeous, 7th floor waterfront condo in the new Madeira Bay Resort in Madeira Beach. Perfectly located directly across the street from the beach, situated on a gorgeous waterfront marina, & just 1 block from John's Pass Village & Boardwalk, enjoy shopping, dining, bars, water sports, boat/bike rentals & more all in walking distance! Newly furnished & well-stocked w/all the comforts of home, enjoy stunning views of the sunrise, intracoastal waterways, & downtown skyline.

KitchenIndoor spacesBeach

Apartment in Madeira Beach

A direct view of the Gulf shoreline is visible from the balcony, showcasing a sandy beach with beach chairs and umbrellas. A private pool is located below, surrounded by a patio area with several lounge chairs, creating an inviting setting for relaxation.

4.9 out of 5 average rating, 128 reviews

Million Dollar View on Gulf-Front Paradise!

This Gorgeous 1st floor, Direct Gulf-Front condo is located on the South end of beautiful Madeira Beach, directly across the street from World Famous John's Pass Village & Boardwalk. Enjoy this 1/1 + premium queen pull-out sleeper sofa with full-sized kitchen, private heated Pool, Outdoor Grills w/ Tiki Huts on one of the Top 10 Beaches in the US. Best Attractions: Dining, Shopping, Boating, Fishing, Dolphin tours, Jet skiing, Paragliding - ALL w/in Walking Distance! Free covered parking GND FL

FamilyKitchenLong stay

4.87 out of 5 average rating, 174 reviews

The single-family beach cottage features a light yellow exterior with red accents and three prominent windows. Surrounding the home, palm trees and landscaping provide a lush atmosphere. A paved area holds several designated parking spaces in front of the cottage, with a stone picnic table nearby.

Cottage in Madeira Beach

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!

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Bungalow in Indian Shores

4.97 out of 5 average rating, 200 reviews

Private Beachfront 2BR BUNGALOW*POOL*PETS ok

DIRECT BEACHFRONT BUNGALOW "MARLIN'S HIDEAWAY." Rare free standing direct beach front house! with private sandy beach backyard! NOT a condo - No crowded elevators, hallways, lobby area, NO faraway parking spaces FEATURES: Great room plan, Sleeps 6, 2 BR + sleeper sofa, all SMART TVs, high speed Wi-Fi. Kitchen is fully equipped. Bathroom is tub/shower with seat. Approx 850 sq ft. Private, fenced deck - PETS ok. BARRETT BEACH BUNGALOWS is a boutique resort ONLY 4 bungalows share heated pool

Indoor spacesFamilyLong stay

Superhost

5.0 out of 5 average rating, 5 reviews

Villa Madeira 604 Luxury Gulf Beachfront Getaway

Villa Madeira #604 is a 3-bedroom, 2-bathroom beachfront condominium that blends comfort with breathtaking Gulf views. The unit features an open living and dining area with large sliding glass doors that lead out to a private balcony overlooking the sugar-white sands of Madeira Beach. With its prime sixth-floor location, this condo offers the perfect setting for enjoying spectacular sunsets each evening. Just a short distance away, you’ll find the famous John’s Pass Village and Boardwalk.

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The aerial view displays a modern four-story condo building with a mix of orange and white façades. Balconies extend from each level, and a marina with boats is visible at the base, along with beach access in the background.

4.84 out of 5 average rating, 129 reviews

Steps to beach with Marina Sunsets – 3 -Bed condo

Steps from Madeira Beach! Enjoy this spacious 3-bedroom , 2-bath newer condo with beautiful marina views, a private balcony, and room for 6 ! 1 min walk to John’s Pass for dining, shopping, fishing, and entertainment. Includes free Wi-Fi, 3 Smart TVs, a full kitchen, washer/dryer in unit , and free parking for one car —everything you need for a relaxing Florida vacation! Watch the boats in the marina while having your morning coffee ! We look forward to hosting you !

KitchenIndoor spacesHospitality

The kitchen features navy blue cabinets, providing a stylish contrast to the stainless steel appliances. A spacious countertop holds essential kitchen gadgets, and a modern backsplash adds texture. Adequate storage is available with cabinets and drawers, contributing to a well-organized cooking space.

4.99 out of 5 average rating, 239 reviews

Rincón Divino MB 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.

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4.94 out of 5 average rating, 118 reviews

A spacious open-concept living area includes a sleek kitchen with modern appliances and ample counter space. A dining table with six chairs and a pool table provide options for entertainment. Bright overhead lights create a welcoming atmosphere, with light-colored cabinets complementing the room.

Condo in Redington Beach

Penthouse,intercoastal, 3/3 views/heated pool

This stylish place to stay is perfect for group trips. Brand New Luxury Madeira Beach Penthouse With Heated Pool 4 floors up with partial beach and intercoastal views, all on a level floor plan 4 stories up with elevator access! Enjoy the comforts of new unit with modern appliances and fixtures in this 3/3 that bolsters a king master bedroom, two guest queen bedrooms all with in suite full bathrooms.

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The beachfront condo complex is positioned along a scenic coastline, showcasing vibrant pastel-colored buildings. Palm trees and parked vehicles are visible in the surrounding areas, with clear blue skies and ocean waves in the background, emphasizing the inviting coastal environment.

4.79 out of 5 average rating, 177 reviews

Amazing Beachfront Complex Close To Johns Pass!

Beach Place is one of the most sort after condos on Madeira Beach! Beach Place Condominiums are located on the beach! and are the closest complex to world-famous John's Pass Village and Boardwalk. Amenities include free WiFi throughout the complex, a beachfront lounge area with tiki huts, a large heated beachside pool, and 3 BBQ grills for cooking your catch!

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4.85 out of 5 average rating, 104 reviews

Great Location at Quiet and Private Building

The La Coquina building in central Madeira Beach gives you some of the best values in a beach vacation spot. Located near all the best beaches, restaurants and activities, this condo will treat you to a relaxing and memorable trip, and comfort you in a beautiful, clean, and updated living space with everything you need to make your trip as easy as possible.

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Popular amenities for Madeira Beach family-friendly rentals

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Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

Apartment in Madeira Beach

A comfortable seating area features a woven hanging chair, positioned on a balcony overlooking the ocean. The view reveals a sandy beach and calm waters, extending to the horizon under a clear blue sky.

4.92 out of 5 average rating, 100 reviews

Oceanfront Luxury paradise

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4.96 out of 5 average rating, 167 reviews

COASTAL CHIC! Luxury Apartment with Oceanviews

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Superhost

The exterior of the Ocean Club building is showcased, featuring a modern design with a white façade and large balconies. Palm trees line the front, enhancing the tropical setting. A welcoming entrance is visible, set against a backdrop of a bright sky with soft clouds.

4.86 out of 5 average rating, 669 reviews

Beachfront Condo in Exclusive Resort

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A modern kitchen area features a large island with seating, complemented by white cabinetry and gleaming countertops. Natural light floods the space through expansive sliding glass doors, which lead to a private terrace with ocean views. A comfortable seating area is arranged nearby.

4.9 out of 5 average rating, 115 reviews

Luxury Seashell Oceanfront Condo with Pool

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Houseboat in Madeira Beach

A cozy living area features a gray sectional sofa adorned with cushions, complemented by a round wooden coffee table. Light filters through multiple windows, highlighting the soft blue and neutrals in the decor. A ceiling fan is overhead, and a potted plant adds a touch of greenery.

4.93 out of 5 average rating, 159 reviews

40ft Floating Bungalow with Resort Perks

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An aerial view showcases a vibrant coastal landscape, featuring a marina filled with boats. The sandy beach extends alongside the tranquil blue waters of the Gulf of Mexico, bordered by colorful buildings. The road leads to the beach, highlighting the proximity to waterfront activities.

4.97 out of 5 average rating, 184 reviews

Penthouse Water View, Pool, @ Johns Pass!

FamilyKitchenQuiet

4.93 out of 5 average rating, 150 reviews

Condo in Indian Shores

Panoramic Gulf View Beachfront Condo

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A private balcony showcases a stunning sunset view, framed by palm trees. The spacious area features a green chair and overlooks the resort's pool and surrounding buildings, creating a serene outdoor space for relaxation.

4.98 out of 5 average rating, 164 reviews

Sunset Nest: Two Bedroom Condo with Sunset Views

Indoor spacesFamilyLong stay

Family- and pet-friendly home rentals

4.92 out of 5 average rating, 145 reviews

A modern three-story home is illuminated at night, highlighting its unique architectural features. The exterior is surrounded by lush greenery, and large windows offer glimpses of the interior. Balconies on the upper levels provide outdoor seating, enhancing the inviting aesthetic.

Home in Madeira Beach

Luxury Living on Madeira Beach

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Bungalow in Redington Beach

4.93 out of 5 average rating, 269 reviews

Single Family Home One Level ~ Walk to the Beach!

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4.87 out of 5 average rating, 111 reviews

Home in Redington Beach

Easy Walk to Beach! 3 BR/2 BATH! Pets OK!

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A wooden walkway leads through a natural landscape, flanked by tropical vegetation and palm trees. The pathway extends toward the horizon, inviting visitors to the nearby ocean. Soft clouds fill the sky, enhancing the serene setting of Madeira Beach.

4.76 out of 5 average rating, 489 reviews

Beach Chill Inn #3 - Studio

FamilyKitchenAir conditioning

4.89 out of 5 average rating, 140 reviews

An aerial view showcases a spacious backyard featuring a heated pool surrounded by colorful lounge chairs. A mini golf area, a basketball court, and a jungle gym with slides are also visible, along with a patio set under umbrellas, creating an inviting outdoor entertainment space.

Home in Seminole

WOW Clearwater Resort! Heated Pool, Pickleball

FamilyIndoor spacesBackyard

4.95 out of 5 average rating, 200 reviews

A sandy path leads through lush greenery towards the beach, framed by overhanging branches. The ocean is visible in the distance, with light reflecting off the water. Shadows create a peaceful atmosphere as the sun casts a warm glow.

Cottage in Indian Shores

Beautiful Beachfront Cottage on the Water

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5.0 out of 5 average rating, 227 reviews

A private backyard features a custom-made pool surrounded by a wooden deck. Lounge chairs and a sun umbrella are positioned nearby, while palm trees and lush greenery offer a tropical ambiance. A white privacy fence encloses the space, enhancing the serenity.

Home in St. Petersburg

Beautiful Tampa Bay Pool Home Near Gulf Beaches

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An outdoor seating area is shown with a glass-top table surrounded by four blue chairs. Two charcoal grills are positioned nearby under palm trees, with a view of the water in the background. The screened cabana features a thatched roof, providing a relaxing atmosphere.

4.91 out of 5 average rating, 217 reviews

Waterside Studio in the heart of TI, walk to beach

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Family-friendly home rentals with a pool

Aerial view of a beachfront building located near Madeira Beach, showcasing proximity to the ocean and nearby establishments. The scene includes colorful structures along the coast, palm trees lining the street, and a clear blue sky reflecting sunlight over the water.

4.93 out of 5 average rating, 112 reviews

Beachfront building across from Johns Pass Village

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4.95 out of 5 average rating, 38 reviews

Direct Beachfront Corner 3BR|GulfView Pool|Madeira

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5.0 out of 5 average rating, 14 reviews

Home in Madeira Beach

Gulf Gardens Madeira Beach Studio Cottage

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A modern kitchen is presented, featuring white cabinetry and light countertops. Equipped with a stove, oven, refrigerator, and dishwasher, it offers essential appliances. Bright pendant lights hang above the island, enhancing the open layout that connects to the living area visible in the background.

5.0 out of 5 average rating, 47 reviews

Newly Renovated Condo with Pool

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Townhouse in Redington Beach

An outdoor rooftop dining area features a large wooden table surrounded by eight wooden chairs, all shaded by a navy umbrella. A stainless steel grill is positioned nearby, alongside a wooden gazebo with teal seating. Ocean views and a painted mural enhance the space.

4.95 out of 5 average rating, 42 reviews

All You Need|Across Beach|Heated Pool|Elevator|Gam

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Apartment in Madeira Beach

A spacious living area features large windows allowing natural light and offering ocean views. Comfortable sofas are arranged around a central coffee table, while a flat-screen TV is mounted on the wall. A beach-themed artwork adds a colorful touch to the room.

5.0 out of 5 average rating, 30 reviews

Beachfront Retreat w/ Panoramic Views and Pool

KitchenIndoor spacesComfort

5.0 out of 5 average rating, 15 reviews

Waterfront Condo | Gulf Views | Beach Access&Pool

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Superhost

A screened-in balcony showcases a spacious seating area with a circular table and multiple chairs. The vibrant sunset sky is visible through the large screen panels, framing a view of the beach and ocean beyond.