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Holiday rentals with a pool in Madeira Beach

Find and book unique homes with a pool on Airbnb

Top-rated rentals with a pool in Madeira Beach

Guests agree: these homes with a pool are highly rated for location, cleanliness and more.

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Top guest favourite
Apartment in Treasure Island
4.96 out of 5 average rating, 188 reviews

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Retreat 🏖️ 🌅 Sunset Serenity - Unwind with views as the sun melts into the horizon. 🚶 Beachside Bliss -Just steps away from powdery sands & shimmering waters of Treasure Island. 🐬 Marine Magic Awaits - Watch dolphins dance and manatees glide right by! ✨ Stylish Coastal Vibes - Immerse yourself modern interiors with a breezy beach flair. 🍽️ Chef’s Dream - Whip up delicious meals in a fully stocked, luxury kitchen. 👩‍💼 Service with Heart - Your comfort is my priority!

Top guest favourite
Apartment in Sunset Beach
4.95 out of 5 average rating, 146 reviews

Stunning BEACH FRONT Condo, KING Size Bed, Balcony

NEWLY FULLY RENOVATED breathtaking beachfront condo on private beach. Walking distance to bars, restaurants, live music and more! Brand new king size bed, high speed wi-fi, Smart TVs with cable/Netflix, heated swimming pool, BBQ/Grills, outdoor tables, showers, beachfront balcony, workspace and you are RIGHT on the beach! Short drive to TPA/PIE airports, Downtown St Pete, Dali Museum & more! The condo is fully equipped with everything you need and run by a Superhost for a perfect Beach vacation!

Top guest favourite
A comfortable living area is furnished with two brown sofas and a light blue coffee table. A television is positioned on a beige console. Artwork depicting beach scenes is displayed on the white wall, while a large sliding door provides access to the balcony with ocean views.
Apartment in Madeira Beach
4.95 out of 5 average rating, 147 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.

Top guest favourite
An aerial view captures the waterfront community, highlighting the proximity to the beach and nearby amenities. Serene blue waters of the canal intertwine with the residential buildings, while the expansive shoreline stretches in the background, offering a picturesque setting for relaxation and exploration.
Apartment in Treasure Island
4.99 out of 5 average rating, 142 reviews

Beach, dolphin/manatee sightings, fishing, sunsets

Welcome to the newly remodeled condo in the Heart of Treasure Island. This bright and modern retreat is perfect for relaxing and avoiding the crowds. Perfect location for beach lovers and wildlife watchers alike with waterfront views of the canal from the living room, kitchen and bedroom windows and beautiful sunsets. Just 2 blocks or a 5 minute walk to the beautiful white sandy beach and a few feet from the canal and pool. Visit nearby great restaurants, John's Pass Boardwalk and live music.

Top guest favourite
An aerial view captures a multi-story condominium overlooking a beach. Lush palm trees surround a heated pool area, with docks lining the waterfront. The expansive coastline is visible in the background, highlighting the scenic proximity of beach and bay.
Apartment in Treasure Island
4.99 out of 5 average rating, 204 reviews

Spectacular beach to bay views from this resort.

Our condo has spectacular water views from the Bay to the Beach. We have a large one of a kind kitchen that is unique to our resort, with granite counter tops, hardwood cabinets, and all stainless steel appliances. Everything you need to prepare a meal is provided along with basic spices and condiments, Coffee, creamer, and sugar. The master bedroom has a new king size bed and walk in closet with all beach gear also available for your use. We have 2 - 50" flat screen TV's with cable as well.

Top guest favourite
A serene beachfront scene showcases soft sand and gentle waves under a clear sky. Lounge chairs are arranged in the foreground, while umbrellas and beach tents are visible further along the shoreline. The bungalow's outdoor seating area is seen, surrounded by lush greenery.
Bungalow in Indian Shores
4.96 out of 5 average rating, 168 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 + heated pool

Top guest favourite
A resort-style swimming pool is surrounded by a spacious patio featuring multiple lounge chairs. The building's exterior is light-colored, with large windows and an inviting entryway. Tropical plants are positioned around the pool area, contributing to a relaxing environment.
Apartment in Treasure Island
4.94 out of 5 average rating, 219 reviews

Where the Sun Meets the Water

This first-story 670 sq-ft, 1BR/1BA condo, is located just a couple of blocks from the white sands of the Treasure Island beaches. Stroll to John’s Pass to find ample local dining and shopping options. Guests have full access to the grounds including a resort-style pool, a shared fishing dock, and a waterfront patio equipped with gas grills, perfect for enjoying a meal and watching as dolphins and birds pass by. 2025. Come visit & stay a while! Operated by Summer Bloom Estates LLC

Top guest favourite
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.
Apartment in Madeira Beach
4.98 out of 5 average rating, 156 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.

Top guest favourite
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.
Apartment in Madeira Beach
4.99 out of 5 average rating, 214 reviews

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.

Top guest favourite
A private tiki hut features a thatched roof, ambient lighting, and a large television. Seating is provided by several lounge chairs and a unique wicker chair, arranged around a stone floor. Lush greenery surrounds the area, enhancing the outdoor experience.
Bungalow in Indian Rocks Beach
4.9 out of 5 average rating, 141 reviews

Tiki Bungalow | Gorgeous Htd Pool | Steps to Beach

An original early 1900 Indian Rocks Beach bungalow, beautiful and bright with pool! Across Gulf Boulevard from 8th Ave beach access with all the comforts of home. Rest in the tropical garden pool, hang out in the private tiki hut out back , hop on the trolley to explore the area. Many shops and restaurants are within walking distance. Splash Harbour water park at the Holiday Inn is walking distance for a day of fun! Have an unforgettable stay! City tax#1479

Guest favourite
A balcony is visible with two white chairs positioned around a small table. The ocean can be seen in the distance, framed by palm trees and a partly cloudy sky, casting gentle shadows across the tiled floor.
Apartment in Madeira Beach
4.88 out of 5 average rating, 200 reviews

Sunsets in Paradise from Balcony with Gulf Views

$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Enjoy coastal charm and modern comfort in this beautifully decorated 2BR/2BA Madeira Beach condo, just steps from the sand and a short stroll to John’s Pass! Relax by the pool with sun shelf or unwind on your private Gulf-view balcony. Features open living, full kitchen, Wi-Fi, and beach gear—towels, chairs, umbrella, and buggy included!

Top guest favourite
An inviting living area features a light gray sofa and a round white coffee table. Large glass doors open to a private balcony with unobstructed views of the Gulf of Mexico, creating a seamless connection with the beachfront landscape.
Flat in Treasure Island
4.92 out of 5 average rating, 138 reviews

Beachfront Condo w/ Ocean View - Newly Renovated!

Newly renovated, 4th floor beachfront condo with a private balcony overlooking the gulf on Treasure Island Beach within walking distance to beaches, onsite pool, bars, and restaurants. View the sunset from your condo where you can relax in a queen size bed, full size sofa bed, and single fold up cot. Inside is a combo living/dining area and fully equipped kitchen, surrounded by beautiful furnishings and art.

Popular amenities for Madeira Beach rentals with a pool

When is the best time to visit Madeira Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price$226 SGD$282 SGD$342 SGD$286 SGD$260 SGD$270 SGD$269 SGD$239 SGD$230 SGD$209 SGD$209 SGD$220 SGD
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Quick stats about holiday rentals with a pool in Madeira Beach

  • Total holiday rentals

    Explore 1,060 holiday rentals in Madeira Beach

  • Nightly prices starting at

    Madeira Beach holiday rentals start at $39 SGD per night before taxes and fees

  • Verified guest reviews

    Over 25,300 verified reviews to help you choose

  • Family-friendly holiday rentals

    790 properties offer extra space & child-friendly amenities

  • Pet-friendly holiday rentals

    Find 70 rentals that welcome pets

  • Rentals with dedicated workspaces

    750 properties have a dedicated workspace

  • Wifi availability

    1,050 of Madeira Beach holiday rentals include wifi access

  • Popular amenities for guests

    Guests love Kitchen, Wifi and Pool across Madeira Beach rentals

  • 4.7 Average rating

    Madeira Beach stays receive an average rating of 4.7 out of 5 from guests

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