
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.

~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!

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!

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.

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.

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.

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

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

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.

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.

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

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!

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
House rentals with a pool

Hibernate in our Bear Creek Home

Heated Pool, Fire Pit, Game Room | Tropic Vibes!

Fun, Funky, Pool, Fire Pit! 4 miles to Beach

Insta Worthy Retreat -Arcade Games- Htd Pool- Golf

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Luxe BeachHouseB w Heated Pool,2 min Walk to Beach

Piece of paradise in Indian Rocks Beach.

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!
Apartment rentals with a pool

Beachfront Condo with Stunning Sunset Views

"Jewel At The Shores" Gulf Front, sleeps 5

Tropical Beachfront Penthouse-Beach Cottages

Beachfront View Balcony. Heated Pool. The Shores

Beautiful Studio on the paradise white sand beach!

Gulf front 1 BR condo-

Five Star Beachfront Condo Newly Renovated

Waterfront Condo w/ Pool & Hot Tub! Mins to Beach!
Other holiday rentals with a pool

Modern Coastal Retreat

Oceanfront 3/2 with 180 degree view BOOK NOW!

Beach Front King Suite, Pool, Grills, Docks #711IR

Sea Side Sunsets Unit C

Peaceful Penthouse Escape | Oceanfront View & Pool

Beach Front, Ocean & Gulf views ~ Las Brisas 506.

Madeira Beach Stunning Beachfront Corner 3 Bedroom

Livin the dream condo, 3 blocks from beach!
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| 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 |
| Avg. temp | 17°C | 18°C | 20°C | 23°C | 26°C | 28°C | 29°C | 29°C | 28°C | 25°C | 21°C | 18°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 $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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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- John's Pass
- Busch Gardens Tampa Bay
- Raymond James Stadium
- Dunedin Beach
- Turtle Beach
- Coquina Beach
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Vinoy Park
- Amalie Arena
- Bean Point Beach
- Jannus Live
- Gulfport Beach Recreation Area
- ZooTampa at Lowry Park
- North Beach
- River Strand Golf and Country Club
- Tampa Palms Golf & Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park




