
Vacation rentals with a pool in Madeira Beach
Find and book unique homes with a pool on Airbnb
Quick stats about vacation rentals with a pool in Madeira Beach

Total vacation rentals
Explore 1,230 vacation rentals in Madeira Beach

Nightly prices starting at
Madeira Beach vacation rentals start at €26 per night before taxes and fees

Verified guest reviews
Over 30,870 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
870 properties have a dedicated workspace

Wi-Fi availability
1,220 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
Top-rated rentals with a pool in Madeira Beach
Guests agree: these homes with a pool are highly rated for location, cleanliness, and more.

Rincón Divino MB 2 Balconies, Ocean & Marina Views
EXCLUSIVE: Saturday checkout is at 5pm. This 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.

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.

Penthouse Condo on Water Steps to Beach+Johns Pass
Escape to paradise at our gorgeous, 7th floor waterfront condo in the new Madeira Bay Resort in Madeira Beach. Perfectly located directly across the street from the beach, situated on a gorgeous waterfront marina, & just 1 block from John's Pass Village & Boardwalk, enjoy shopping, dining, bars, water sports, boat/bike rentals & more all in walking distance! Newly furnished & well-stocked w/all the comforts of home, enjoy stunning views of the sunrise, intracoastal waterways, & downtown skyline.

Million Dollar Gulf-Front View!
This Gorgeous 1st floor, Direct Gulf-Front condo is located on the South end of beautiful Madeira Beach, directly across the street from World Famous John's Pass Village & Boardwalk. Enjoy this 1/1 + premium queen pull-out sleeper sofa with full-sized kitchen, private heated Pool, Outdoor Grills w/ Tiki Huts on one of the Top 10 Beaches in the US. Best Attractions: Dining, Shopping, Boating, Fishing, Dolphin tours, Jet skiing, Paragliding - ALL w/in Walking Distance! Free covered parking GND FL

Villa Madeira
Property Type Condo Unit Code VM204 Beds 1 king bed, 1 queen bed, 2 twin beds Bathrooms 2 bathrooms Rooms Sleeps 6 Reserved Parking for 1 Vehicle, Guest Parking for Others Pets No pets allowed. Living Central Air Conditioning, High Speed Internet, Ironing Board, Linens, Washer & Dryer Business Nearby ATM, Nearby Bank, Nearby Internet Cafe Kitchen Coffee Maker, Cookware, Full Kitchen, Entertainment Smart TV Outdoor Balcony, Beach, Outdoor Shower, Pool Geographic Close to John's Pass, On Beach

Beachfront building across from Johns Pass Village
Beachfront building - head downstairs to enjoy the white sand beaches of Madeira Beach! Partial beach view from the large balcony. Updated 2-bedroom condo with contemporary furniture. Prepare meals in the fully equipped kitchen or walk across the street to John's Pass Village & Boardwalk with many restaurants, retail stores, ice cream shops, sunset cruises, jet ski rentals and more! Condo offers walkability and beach access downstairs. Price is discounted - pool is closed until January 2027.

Family Friendly Beach Cottage in Madeira Beach, FL
Mad Beach Cottage is a single family home in the Surf Song Resort on Madeira Beach 60 flip-flop steps to SAND! No streets, boardwalks or stairs! You'll enjoy a heated pool, 3 Weber grills, shuffleboard and sundeck with lounge chairs for gazing at spectacular sunsets every night. It's located across from famous John's Pass Fishing Village Boardwalk for shopping, dining, ice cream, coffee, live music, brew pubs, dolphin/fishing/sunset/pirate boat cruises, wave runner/kayak rentals. 5* LOCATION!

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 share heated pool

Steps to beach with Marina Sunsets – 3 -Bed condo
Steps from Madeira Beach! Enjoy this spacious 3-bedroom , 2-bath newer condo with beautiful marina views, a private balcony, and room for 6 ! 1 min walk to John’s Pass for dining, shopping, fishing, and entertainment. Includes free Wi-Fi, 3 Smart TVs, a full kitchen, washer/dryer in unit , and free parking for one car —everything you need for a relaxing Florida vacation! Watch the boats in the marina while having your morning coffee ! We look forward to hosting you !

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.

Beachfront Condo in Exclusive Resort
The most stunning views from this brand new condo directly on Treasure Island Beach. This lovely unit is on the 4th, 5th, or 6th floor and provides sweeping views of the ocean. This units has 2 bedrooms and 2 full bathrooms. The inviting open concept living area has one of the best views of the ocean, especially when the retractable sliding doors are opened. The dining table on your private balcony provides a perfect dining area, with the ocean providing a beautiful backdrop.

COASTAL CHIC! Luxury Apartment with Oceanviews
Welcome to our Gulf View Condo SEASIDE #1604 at the "Madeira Bay Resort" - just steps from the beautiful white-sanded Beach and famous John's Pass! Built in 2020, you will enjoy brand new amenities, luxurious furnishings, memory foam beds, an electric fireplace, a gourmet kitchen and all beach essentials, so you only have to pack your flip flops and come on over!
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath

Insta Worthy Retreat -HTD Pool- Arcade Room- Golf

Waterfront Luxury Heated Pool/Hot Tub 5 bedrooms

Clearwater-Pickleball/SltPool/Golf/Theatre/Arcade

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Sparkling Modern Pool Home with Guest Bungalow!

Stunning Lakefront-King bed - 10 min to beaches
Condo rentals with a pool

Beach Front at “The Shore”

*Shore Thing* Walk to Beach | Intercoastal Views

Sunset Nest: Two Bedroom Condo with Sunset Views

Luxury Seashell Oceanfront Condo with Pool

Spectacular beach to bay views from this resort.

Villa Madeira 604 Luxury Gulf Beachfront Getaway

Huge Private Balcony, Pool & Hot Tub. Sunsets!

Sept Sale 30% off - Steps to Beach, Dining & Shops
Other vacation rentals with a pool

Beachfront Retreat w/ Panoramic Views and Pool

Luxury Penthouse Beach Condo

Beachfront Condo | On Sand | 3 Room | Heated POOL

Waterfront Condo | Gulf Views | Beach Access&Pool

Direct Beachfront Corner 3BR|GulfView Pool|Madeira

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

New Luxury 3BR Walk to Beach Pool, Spa + Parking

MBR 502 - Beach-Pool-Hot Tub-Walk to John's Pass!
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €176 | €214 | €255 | €206 | €174 | €182 | €177 | €157 | €151 | €158 | €163 | €170 |
| 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 |
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