Family-friendly holiday rentals in Madeira Beach

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

EXCLUSIVE: Saturday checkout is at 5pm. This 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.

Indoor spacesFamilyDecor

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.

FamilyKitchenAccuracy

4.79 out of 5 average rating, 161 reviews

Bay & Blvd | Steps to Beach, Pool & John's Pass

Sun-soaked days & evening sunset skies, warm Gulf water & sugar-white sand right outside your door — welcome to Madeira Beach, one of America's most celebrated family beach destinations. This bright coastal condo puts you steps from the beach & a short walk to Johns Pass Village & Boardwalk. Heated pool, hot tub, fitness center, parking & beach gear all included — no hidden extras. Perfect for families, couples & friend groups. Just grab your sunscreen and go — we've got everything else covered!

Indoor spacesFamilyCondition

Cottage in Redington Beach

Entire home and yard 2 /1 with two sleep sofas

This lovely beach bungalow has all the updates, including a walk-in shower, on-demand hot water, quartz 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.

Indoor spacesKitchenQuiet

4.81 out of 5 average rating, 283 reviews

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.

KitchenFamilyNearby

Townhouse in Madeira Beach

A view through a screened balcony showcases a sandy beach with individuals enjoying the sun. Colorful beach umbrellas and towels are positioned on the sand, and the calm ocean stretches into the distance under a clear blue sky.

Villa Madeira

Property Type Condo Unit Code VM204 Beds 1 king bed, 1 queen bed, 2 twin beds Bathrooms 2 bathrooms Rooms Sleeps 6 Reserved Parking for 1 Vehicle, Guest Parking for Others Pets No pets allowed. Living Central Air Conditioning, High Speed Internet, Ironing Board, Linens, Washer & Dryer Business Nearby ATM, Nearby Bank, Nearby Internet Cafe Kitchen Coffee Maker, Cookware, Full Kitchen, Entertainment Smart TV Outdoor Balcony, Beach, Outdoor Shower, Pool Geographic Close to John's Pass, On Beach

Indoor spacesFamilyWi-Fi

4.89 out of 5 average rating, 156 reviews

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

Beachfront building - head downstairs to enjoy the white sand beaches of Madeira Beach! Partial beach view from the large balcony. Updated 2-bedroom condo with contemporary furniture. Prepare your meals in the fully equipped kitchen or walk across the street to John's Pass Village & Boardwalk which offers restaurants, retail stores, ice cream shops, sunset cruises, jet ski rentals and more! The condo offers walkability and beach access downstairs. The pool is currently closed due to a leak.

Indoor spacesFamilyAccess

4.87 out of 5 average rating, 175 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

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

KitchenIndoor spacesSleep quality

4.97 out of 5 average rating, 200 reviews

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.

FamilyKitchenBeach

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 !

KitchenFamilyBathroom

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!

Penthouse corner unit with stunning water view from the living room, bedrooms and balcony! This waterfront condo is in prime location. A block away from Johns Pass Boardwalk (#1 tourist destination in the county) and RIGHT across from the pristine white sands & sunsets of the Gulf of Mexico. The property offers a heated pool, hot tub, fitness room & event center. Our condo has everything you need including fully stocked kitchen, laundry in unit, high speed wifi & beach equipment.

Indoor spacesKitchenQuiet

Popular amenities for Madeira Beach family-friendly rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

Family-friendly home rentals with a hot tub

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.

Condo in Treasure Island

Beachfront Condo in Exclusive Resort

Indoor spacesKitchenView

4.86 out of 5 average rating, 669 reviews

4.96 out of 5 average rating, 167 reviews

COASTAL CHIC! Luxury Apartment with Oceanviews

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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, 101 reviews

Oceanfront Luxury paradise

FamilyIndoor spacesHot tub

4.91 out of 5 average rating, 117 reviews

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.

Condo in Treasure Island

Luxury Seashell Oceanfront Condo with Pool

FamilyIndoor spacesGetting around

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.

40ft Floating Bungalow with Resort Perks

FamilyKitchenView

4.92 out of 5 average rating, 162 reviews

4.98 out of 5 average rating, 164 reviews

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.

Condo in Treasure Island

Sunset Nest: Two Bedroom Condo with Sunset Views

Indoor spacesFamilyHospitality

4.93 out of 5 average rating, 150 reviews

Condo in Indian Shores

Panoramic Gulf View Beachfront Condo

KitchenIndoor spacesOutdoor spaces

Condo in North Redington Beach

A serene beachfront view is captured under a clear blue sky. The vivid turquoise water reflects sunlight, creating a shimmering pathway across the calm sea. Gentle waves roll onto the soft sandy shore, where a person is seen walking along the beach.

Toes in the Sand Beachfront penthouse condo

FamilyKitchenBathroom

4.92 out of 5 average rating, 130 reviews

Family- and pet-friendly home rentals

4.88 out of 5 average rating, 112 reviews

Home in Redington Beach

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

FamilyKitchenSleep quality

4.92 out of 5 average rating, 146 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

KitchenIndoor spacesCleanliness

Superhost

4.91 out of 5 average rating, 108 reviews

Beachside Escape | 2 min walk to Shore · Sleeps 7

KitchenIndoor spacesComfort

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.

4.77 out of 5 average rating, 490 reviews

Beach Chill Inn #3 - Studio

KitchenIndoor spacesHot tub

Bungalow in Redington Beach

Single Family Home One Level ~ Walk to the Beach!

Indoor spacesKitchenValue

4.93 out of 5 average rating, 269 reviews

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

FamilyIndoor spacesBeach

4.95 out of 5 average rating, 202 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

KitchenIndoor spacesAmenities

Townhouse in Indian Rocks Beach

The two-story condo building features a light-colored exterior, spacious balconies, and palm trees lining the entrance. The proximity to the sandy beach and vibrant blue Gulf water is visible in the background, showcasing a serene coastal atmosphere.

♥ OCEANFRONT VIEW ♥ BEACHFRONT CONDO ♥ NEW ♥ U3 ♥

FamilyKitchenEV charging

4.96 out of 5 average rating, 161 reviews

Family-friendly home rentals with a pool

5.0 out of 5 average rating, 14 reviews

Home in Madeira Beach

Gulf Gardens Madeira Beach Studio Cottage

FamilyBarbecueComfort

4.95 out of 5 average rating, 38 reviews

Direct Beachfront Corner 3BR|GulfView Pool|Madeira

KitchenFamilyCondition

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

Indoor spacesKitchenAmenities

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

Superhost

4.86 out of 5 average rating, 14 reviews

Beachfront Condo | On Sand | 3 Room | Heated POOL

FamilyKitchenCleanliness

The living room features a gray sofa with decorative pillows, a recliner chair, and a coffee table. A large TV is mounted above a stone fireplace. Soft lighting is provided by floor lamps and ceiling fans, with light gray tiles covering the floor.

5.0 out of 5 average rating, 19 reviews

Gorgeous Condo in Madeira Beach Yacht Club!

Indoor spacesKitchenAccess

4.97 out of 5 average rating, 78 reviews

A bright bedroom features a spacious bed with blue bedding and accent pillows. A wooden dresser is positioned against the wall, complemented by a lamp and decorative elements. A television is mounted above the dresser, while ambient light is provided by a ceiling fan.

Condo in Redington Beach

Luxury Beach Condo - 3BR/3BA

KitchenFamilyAccess