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Family-friendly vacation rentals in Madeira Beach

Find and book unique family-friendly homes on Airbnb

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Popular amenities for Madeira Beach family-friendly rentals

Family-friendly home rentals with a pool

Top guest favorite
The image features a heated private pool surrounded by sunbeds and lush greenery. Palm trees provide shade and a serene atmosphere. The pool area is enclosed with a white fence, and nearby buildings offer a relaxed vacation setting. Clear skies enhance the inviting pool scene.
Condo in Indian Shores
4.96 out of 5 average rating, 143 reviews

Good Times and Tan Lines @ #105intercoastal

JenaRating, 5 stars3 weeks ago
Excellent beach place! Very spacious and quiet and clean! Easy access to the beach and the pool was an added bonus! Host has everything you would need for a great beach getaway!! Fully stocked with beach chairs, umbrella, cart, and beach toys. Even equipped with beach towels. Great location for a little quiet but close to many restaurants and bars. While a staycation for us since my own beach home was destroyed by Hurricane Helene, this was a perfect place to feel right at home.
Guest favorite
A three-story home is showcased beside a private heated pool and spa. Lush landscaping surrounds the area, highlighting the inviting turquoise waters. Outdoor seating is visible under a covered patio, with stairs leading to the upper levels of the home.
Home in Seminole
4.95 out of 5 average rating, 295 reviews

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

ClaireRating, 5 starstoday
This home was the perfect place to stay for our family vacation. Charlie was responsive and provide incredible recommendations anytime we asked. The yard was private and secure and the neighborhood was quiet. The home has everything we needed! We didn't have to travel more than 30 minutes to beaches, delicious restaurants and ice cream. I would absolutely stay here again!
Superhost
A private heated pool is surrounded by a spacious deck featuring lounge chairs and a dining area. Palm trees provide shade while boats are visible at the dock. String lights overhead create a relaxed ambiance, and the tranquil water reflects the blue sky.
Home in Indian Rocks Beach
4.97 out of 5 average rating, 116 reviews

Ocean Dreaming: Waterfront Home with Heated Pool,

MelissaRating, 5 stars2 months ago
We would go back in a heartbeat! The house and location was perfect! Our kids loved the pool and being able to kayak and paddle board right from the dock was amazing! We saw dolphins multiple times a day and had fun fishing. The golf cart was perfect for getting to the beach and plenty of restaurants, including an ice cream shop! I would totally recommend this place!
Superhost
A balcony view that captures the tranquil beach scene, featuring soft pastel hues in the sky. A round table with intricate design sits next to two woven chairs. Below, umbrellas dot the sandy beach, while gentle waves touch the shore.
Apartment in Belleair Beach
4.7 out of 5 average rating, 461 reviews

BEACHFRONT Condo - Belleair Beach Club - RENOVATED

MichelleRating, 5 stars3 weeks ago
Mathew's place was exactly what I needed. Calm, quiet and very peaceful. I didn't hear the neighbors the whole time I was there. The beach was literally right out the window. So getting down there was very easy. Having a beach chair, cooler and bag in the condo was very convenient. The condo was very clean and homey. I liked being able to cook for myself and never having to leave the complex. I will definitely stay here again!!
Top guest favorite
A spacious living area is furnished with a large sectional sofa and additional seating, centered around a rustic coffee table. Large windows provide natural light, while a ceiling fan adds comfort. An open layout connects to a dining area and kitchen in the background.
Home in Tarpon Springs
4.96 out of 5 average rating, 362 reviews

Tarpon Fun'n Sun-Pool, Beaches + Backyard Chickens

DavidRating, 5 stars3 weeks ago
Overall our stay was great! Jeff was very responsive, and left us a lot of recommendations for local restaurants. The house was very clean and the pictures accurately reflected how to house looked. The only downsides were the large bugs that somehow got in the home. There were 3 occasions this happend but they seemed harmless. The net around the pool had a tear in it allowing spiders and lizards inside of the pool area but they stayed around the outside of the pool so we could avoid them.
Top guest favorite
Apartment in Indian Shores
4.96 out of 5 average rating, 195 reviews

Barefoot Beach Resort Indian Shores

JennieRating, 5 stars1 month ago
The perfect place for a family beach vacation - we could not have asked for more! Ewa’s condo at Barefoot Beach Resort was spotless, well appointed and perfect for our family beach vacation. Her kitchen was stocked, she had every beach accessory imaginable and the beds and linens were extremely comfortable. Ewa was a great host and we cannot wait to go back!
Top guest favorite
Apartment in Dunedin
4.99 out of 5 average rating, 244 reviews

Tropical Paradise

NancyRating, 5 stars1 week ago
Perfect oasis for a tropical getaway! Everything was just as described. Really enjoyed the use of bikes and Honeymoon Island is absolute paradise! Lori ands Gary were very attentive and quickly handled anything we needed!
Top guest favorite
A large outdoor pool is visible, surrounded by palm trees and poolside lounge chairs. The clear water reflects the blue sky, creating a serene atmosphere. The pool area is fenced and well-maintained, with sun loungers situated along the water's edge.
Condo in Indian Shores
4.96 out of 5 average rating, 135 reviews

"Sunsational" Indian Shores Getaway!

TraceRating, 5 stars2 weeks ago
Great stay and exactly what we had hoped for. Very relaxing!

Family-friendly home rentals with air conditioning

Guest favorite
An aerial view captures the Aqua Beach Condo location, highlighting proximity to both the Intracoastal Waterway and the beach. Lush greenery and the vibrant blue waters contrast with the nearby buildings, while the sandy shoreline stretches along the coast under a clear sky.
Condo in Indian Rocks Beach
4.94 out of 5 average rating, 206 reviews

Steps to the Beach - Modern & Updated 2 BR Condo

DawnRating, 5 stars2 weeks ago
We thoroughly enjoyed our stay at Veronika’s place. Everything was clean and so well appointed inside. Literally steps to the beach with everything you could possibly need during your stay. Walkable to our two favorite restaurants, and CVS. Exceeded all expectations and we look forward to coming back.
Guest favorite
A spacious wooden dock extends over calm waters, flanked by moored boats under a clear blue sky. The dock features sturdy railings and provides an inviting access point to the waterfront scenery.
Home in Indian Rocks Beach
4.85 out of 5 average rating, 250 reviews

Amazing water front view home newly renovated

WilfredoRating, 5 stars5 days ago
Amazing host, along with an amazing place to stay. Beautiful home with a view worth the price.
Guest favorite
A vibrant sunset casts warm orange and yellow hues across the sky, reflecting on the tranquil Gulf waters. Silhouetted palm trees frame the scene, enhancing the coastal ambiance. The horizon showcases the sun gradually setting, providing a serene view for relaxation.
Condo in Madeira Beach
4.85 out of 5 average rating, 84 reviews

Special August 25'- All Rooms Direct Beach Front

SarahRating, 5 stars1 week ago
Great location and a nice space. My family loved the big pool area and that it was right next to the beach.
Superhost
A shaded lounging area features a comfortable chair with a patterned cushion, facing a serene waterfront view. In the background, a dock extends into the calm water, surrounded by lush greenery and decorative plants.
Condo in Indian Rocks Beach
4.96 out of 5 average rating, 121 reviews

Villa Al Golfo Pristine Waterfront Oasis

RhondaRating, 5 stars5 days ago
We honestly couldn’t have picked a better place to celebrate our birthdays. From the moment we arrived, the owners were so warm and inviting. They surprised us with a few welcome goodies, which was such a thoughtful touch and really made us feel at home right away. The unit was beautiful—clean, spacious, and honestly felt like a little slice of luxury. The bed was super comfortable, and the towels and bedding were incredibly soft and fresh—you can tell they really take pride in keeping everything in top shape. The view of the bay was amazing, and we got to watch dolphins swim by from the unit, which was just magical. They had canoes available for us to use, which made for a fun and peaceful afternoon out on the water. The location was perfect—just a short walk to the beach, shops, and restaurants. They gave us some great local restaurant recommendations too, and we ended up trying a few that we might have otherwise missed. Can’t wait to come back. Thanks Lyn & Frank
Top guest favorite
A spacious yard is presented under the shade of mature trees, featuring a colorful swing set and a hanging basket chair. Lush green grass covers the ground, and a light-colored house is seen in the background, enhancing a peaceful outdoor environment.
Guesthouse in Seminole
4.95 out of 5 average rating, 245 reviews

Private Apt/3miles from beaches/Treehouse.like

RichardRating, 5 stars1 month ago
I stayed at Karens place for about a week while working and visiting family. It was beautiful and exceptionally clean. Check in very easy with the button lock box, and located nearby Walsingham park is good for walks and quiet views. Karen was really responsive with communication. Would happily stay here again. A+
Guest favorite
An open kitchen area is equipped with stainless steel appliances, including a microwave and oven. A granite countertop surrounds the kitchen, complemented by wooden cabinets. A dining table with place settings is visible, along with a cozy seating area featuring a sofa and coffee table in the background.
Cottage in Indian Rocks Beach
4.87 out of 5 average rating, 151 reviews

#1 - 3 min walk to the beach

BarbaraRating, 5 stars3 weeks ago
Great stay at Vanessa’s place very clean and quiet easy walk to beach
Guest favorite
A cozy cottage is showcased, featuring a yellow exterior with white shutters. A white picket fence borders the front yard, which is adorned with green grass and shrubs. Two blue chairs are positioned on the porch, inviting relaxation.
Guesthouse in Pinellas Park
4.87 out of 5 average rating, 270 reviews

pet friendly on an equestrian farm

RoslynRating, 5 stars2 months ago
As a solo 74 year old gal with an English cocker, safety is most important. I was very comfortable and felt safe. there. Just a lovely place and nice people
Top guest favorite
The image captures a serene outdoor area featuring a charming entrance to the cottage. Surrounding tropical plants and tall trees create a lush environment. A decorative fountain stands to the left, and comfortable seating under an umbrella adds to the inviting atmosphere.
Guesthouse in Largo
4.99 out of 5 average rating, 332 reviews

Paradise Cottage Largo Beaches 1 mile $89 private

PaigeRating, 5 stars3 weeks ago
There are so many things I could say about our stay at Paradise Cottage and our hosts Michael and Ron. There are not enough adjectives to describe how nice, kind, wonderful and accomodating the property was. My sister and I spent several days there helping my nephew move into an apartment nearby. The cottage was very quaint and well appointed. The towels in the bathroom were plush and had all the supplies we needed. The added touches of the oranges, coffee, bagels were a pleasant surprise. They even had beach gear for us to use. I cannot say enough about how wonderful our hosts were and they really made us feel welcome. We hope to come back and visit them soon.

Family-friendly home rentals with Wifi

Top guest favorite
An outdoor deck features a round table surrounded by sturdy, high-back chairs, shaded by a large umbrella. A tiki bar with bamboo accents and a comfortable seating area is visible in the background, inviting relaxation. Sliding glass doors lead into the indoor living space.
Condo in Indian Rocks Beach
4.98 out of 5 average rating, 61 reviews

Beach Retreat III

AlexRating, 5 stars3 weeks ago
We had a great time at this conveniently located unit. Very walkable area with a great beach across the street that isn’t crowded. Great restaurants for breakfast, lunch, & dinner within walking distance. The patio of the unit is a great place to have coffee or enjoy a meal!
Top guest favorite
The image showcases a pool area overlooking a serene waterway, bordered by palm trees. Sunbeds are positioned around the pool, and lush greenery is visible in the foreground. A tranquil sky with scattered clouds enhances the view of the water, creating a peaceful atmosphere.
Condo in St. Petersburg
4.96 out of 5 average rating, 28 reviews

BOCA CIEGA Condo - 107

LindsayRating, 5 stars1 week ago
This place is extremely beautiful! The other tenants are so kind which adds to the experience!
Superhost
A balcony view features a metal flamingo sculpture and a scenic waterway lined with boats. Lush greenery and a manicured lawn are visible below, with buildings reflecting the blue sky in the background. The overall setting conveys a peaceful outdoor space.
Condo in Madeira Beach
4.87 out of 5 average rating, 55 reviews

Madeira Bay Resort 311 condo sleeps 7 w/ Amenities

NisantRating, 5 stars1 month ago
My family and I had a great time at the Madeira Bay Resort! Check-in was easy and our stay was very comfortable - everything was as described. The boardwalk was a short walk away, the building was a short walk to the beach, and the pool was just adjacent to the building! All in all, we'll definitely consider staying here again if we come back to the area!!
Top guest favorite
A modern kitchen arrangement features sleek stainless steel appliances, including a stove, microwave, and dishwasher. Light-colored cabinetry is paired with a large stone countertop. The open space is well-lit with recessed lighting, and views of the balcony area are visible through the nearby sliding glass doors.
Condo in Madeira Beach
4.97 out of 5 average rating, 31 reviews

Updated Beachfront Condo, Pool, walk to Johns Pass

ElizaRating, 5 stars1 week ago
I brought a group of teenagers for a girls week at the beach, and we loved this place! Steps from our room to the beach and directly across the street from John’s Pass, where the girls enjoyed the shops and water sports activities. The beds were super comfy, and we had plenty of space - more than enough - for the 5 of us. Alex was super helpful in getting us checked in early as our flight had us arriving well before check in time. We would definitely come back!
Guest favorite
The living area features a leather couch facing a coffee table, complemented by a ceiling fan and high ceilings. A bar area with stools is visible, along with an airy kitchen space. Decor elements include wall art and acoustic guitars, contributing to a creative ambiance.
Condo in Seminole
4.96 out of 5 average rating, 26 reviews

Tampa Bay/St Petersburg Condo

AmandaRating, 5 stars2 weeks ago
Great place to stay! It was exactly the way it was described in the listing. Kamil was super responsive and answered any questions quickly! Highly recommend!
Superhost
A view from the balcony showcases the pool area and adjacent beach. Lounge chairs surround the rectangular pool, with shaded umbrellas and tables positioned nearby. The sandy beach extends toward the horizon, framed by the gentle waves of the Gulf of Mexico under a partly cloudy sky.
Condo in Indian Shores
4.88 out of 5 average rating, 57 reviews

AWESOME PENTHOUSE CONDO ON GULF OF MEXICO

DavidRating, 5 stars1 month ago
This is our second time staying here in one year and both times were fantastic. Perfect location and beautiful condo. We will definitely stay again!! David & Robin
Top guest favorite
A neatly made king bed features decorative pillows and a soft throw blanket. A tray with a cup and cookies rests atop the bed. Fresh roses are arranged in a vase beside a seashell. A large window offers a view of the ocean and allows natural light to fill the room.
Condo in Madeira Beach
4.88 out of 5 average rating, 60 reviews

Beach Front, Ocean & Gulf views ~ Las Brisas 506

JeanmarieRating, 5 stars3 weeks ago
Beautiful beautiful venue - beach right outside the door. Balcony great for just sitting and listening and watching the water. Host very receptive and helpful. Great restaurants right across the street. We found it very restful and relaxing.
Top guest favorite
Condo in Indian Rocks Beach
5 out of 5 average rating, 28 reviews

Beachfront Bliss! Directly on Gulf with pool!

KelseyRating, 5 stars1 month ago
We had a great time with our 3 young children. Everything we needed was there- chairs, umbrella, toys, a wagon. Bliss was very accessible and responsive to all texts. The location of the condo, right on the beach, was so convinient which isn’t always the case when traveling with kids. The beds and pillows were so comfortable! We will definitely be back if we ever have the opportunity again.

Quick stats about vacation rentals that are family-friendly in Madeira Beach

  • Total rentals

    840 properties

  • Nightly prices starting at

    ﺩ.ﺇ184 before taxes and fees

  • Total number of reviews

    20K reviews

  • Pet-friendly rentals

    100 properties allow pets

  • Rentals with a pool

    710 properties have a pool

  • Rentals with dedicated workspaces

    580 properties have a dedicated workspace

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