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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 Sunset Beach
4.95 out of 5 average rating, 155 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!

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
4.94 out of 5 average rating, 150 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 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, 209 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.

Guest favourite
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.
Houseboat in Madeira Beach
4.94 out of 5 average rating, 115 reviews

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**

Guest favourite
A bright living area features large windows that allow natural light to filter in, creating an airy ambiance. A comfortable seating arrangement is complemented by a dining table set with round placemats. A ceiling fan adds a cooling feature, and beach-themed artwork decorates the walls.
Apartment in Madeira Beach
4.8 out of 5 average rating, 207 reviews

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.

Guest favourite
The modern condominium complex features multiple balconies overlooking a pool area. Vibrant tropical plants surround the pool deck, which is equipped with lounge chairs and shaded umbrellas. Clear blue skies and palm trees add to the inviting outdoor space.
Apartment in Treasure Island
4.9 out of 5 average rating, 167 reviews

Beachfront Condo Resort on Treasure Island

Be among the first to experience this new condo resort. 992 sq ft of beachfront luxury with full resort amenities. These upper-floor corner units have gorgeous views of the ocean, and each room has a window with beach views. With 2 bedrooms and 2 bathrooms and a pullout couch in the living room, these units can comfortably house 6 people. After arriving in your open concept living area, you will access your private balcony through retractable sliding doors that let the ocean air in.

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, 161 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.

Guest favourite
Flat in Madeira Beach
4.74 out of 5 average rating, 228 reviews

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.

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, 217 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
An open-concept living area features a light-colored, patterned sofa paired with a wooden coffee table. A large flat-screen TV is mounted on the wall, and a serene window nook offers natural light, enhancing the coastal charm of the space.
Apartment in Treasure Island
4.96 out of 5 average rating, 192 reviews

~Shore Thing~ Coastal Exquisite Waterfront Condo

🏖️ Shore Thing Condo 🏖️ 🌅 Sunset Serenity — Relax as the sun melts into the horizon. 🚶Beachside Bliss — Just steps from powdery sands and shimmering Treasure Island waters. 🐬 Marine Magic — Spot dolphins dancing and manatees gliding by. ✨ Stylish Coastal Vibes — Modern interiors with breezy beach flair. 🍽️ Chef’s Dream — Cook with ease in a luxury kitchen. 👩‍💼 Service with Heart — Your comfort always comes first

Guest favourite
An inviting courtyard area is showcased, featuring a sparkling heated pool surrounded by lounge chairs. Lush greenery and well-maintained gardens add a natural touch, while the two-story yellow building encloses the area, creating a serene and communal atmosphere for relaxation.
Apartment in Redington Beach
4.86 out of 5 average rating, 352 reviews

Royal Orleans at Redington Beach ( Studio )

Royal Orleans 208 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

Top guest favourite
Apartment in Madeira Beach
4.99 out of 5 average rating, 103 reviews

Beach Front Madeira Beach

Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.

Popular amenities for Madeira Beach rentals with a pool

When is the best time to visit Madeira Beach?

MonthJanFebMarAprMayJunJulAugSepOctNovDec
Avg. price₹15,610₹19,490₹23,641₹19,761₹17,956₹18,678₹18,588₹16,513₹15,881₹14,437₹14,437₹15,159
Avg. temp17°C18°C20°C23°C26°C28°C29°C29°C28°C25°C21°C18°C

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 ₹2,707 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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