
Vacation 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.

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.

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.

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**

Experience the charm of Gulf Gardens. The Pelican.
Come visit the gem of Madeira Beach, and discover the charm that has visitors coming back for decades. Enjoy a quiet, clean tropical old Florida feel that's hard to find anywhere in this sought after beach community. This property features lush landscaping and one of the largest, cleanest pools you'll find. Our visitors appreciate the attention to detail the owners put into making Gulf Gardens a special place they want to visit year after year. The white sands of Madeira Beach are calling.

Gulf view Condo with pool in Clearwater/St. Pete
Located between Clearwater Beach & St. Pete Beach, this fully furnished Studio features a full kitchen with a full-sized stainless steel refrigerator and dishwasher, granite countertop, microwave, kitchenware, a Queen bed, a queen size sleeper sofa, closet space, and new AC. This quaint 35-unit resort condo offers a heated pool with tables, lounge chairs and gas grill within a smoke-free tropical courtyard. Just step out the front door for a view of the gulf & 3 mins. walk to the beach.

Stylish Madeira Beach Resort Gulf View John's Pass
$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Enjoy beachside bliss in this stylish 2BR/2BA Madeira Beach condo—just steps from the sand (across the street) and a short walk to John’s Pass! Relax on your private balcony with Gulf views or soak up the sun at the pool. Includes full resort access, Wi-Fi, parking, and beach gear—towels, chairs, umbrella, and buggy. Elevator to the 4th floor for easy access to your coastal getaway!

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.

Waterfront condo! Fishing pier! Heated pool hottub
Wake up to stunning waterfront views! Unwind in this bright studio overlooking Boca Ciega Bay, sip coffee on your private balcony while watching dolphins. Highlights: • Direct waterfront views from balcony • Heated pool, spa & fitness center overlooking bay • Minutes to Madeira Beach, St. Pete, & War Veterans’ Memorial Park • Cozy king bed • Close to boat rentals, trails, and waterfront dining Perfect for romantic getaway or peaceful solo escape!

~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

Royal Orleans and 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.

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
House rentals with a pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Cozy Stylish Home w/ Heated Pool & Big Parking

Ocean Dreaming: Waterfront Home with Heated Pool,

3BR St. Pete Home, Heated Pool, 5 Min To Beaches

Resort Pool Home with Pool Cabana 🏝6 MIN to BEACH-

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Palm Paradise - Family Amenities+Central Location
Condo rentals with a pool

2 BR/2 BA Key West Retreat, A+Pool, 3mi to Beach

Relax in a Newly Renovated Beach Front Paradise

Waterfront Condo - Dolphin sightings-Walk to beach

Waterside Studio in the heart of TI, walk to beach

Luxury Beach Condo - 3BR/3BA

Beachfront building across from Johns Pass Village

Tropical Beachfront Penthouse-Beach Cottages

Beachfront Bliss | King Bed | Heated Pool + Views!
Other vacation rentals with a pool

Beach-steps away! Waterfront Pool View!5

Amazing Ocean View, Pool @ Mad. Beach- John's Pass

Madeira Beach getaway; walk to the beach

Oceanfront 3/2 with 180 degree view BOOK NOW!

Luxury Ocean Front Duplex

Tranquil "Ocean Breeze Retreat"

NEW Waterfront Oasis with Gameroom

Sunny St. Pete Getaway with Dolphins
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | G$36,195 GYD | G$45,192 GYD | G$54,816 GYD | G$45,820 GYD | G$41,635 GYD | G$43,309 GYD | G$43,100 GYD | G$38,288 GYD | G$36,823 GYD | G$33,476 GYD | G$33,476 GYD | G$35,149 GYD |
| 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 vacation rentals with a pool in Madeira Beach

Total vacation rentals
Explore 1,060 vacation rentals in Madeira Beach

Nightly prices starting at
Madeira Beach vacation rentals start at G$6,277 GYD per night before taxes and fees

Verified guest reviews
Over 25,300 verified reviews to help you choose

Family-friendly vacation rentals
790 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 70 rentals that welcome pets

Rentals with dedicated workspaces
750 properties have a dedicated workspace

Wi-Fi availability
1,050 of Madeira Beach vacation rentals include wi-fi 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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