
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.

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!

Pearl of the Sea, 1 BDRM, 2 min walk to the beach
Please note, the gym, jacuzzi, and hot tub are temporarily closed(hurricane damage) Completely remodeled, beach theme decorated, a beautifully furnished second-floor condo just steps away from the white silky sandy beach! Ideal for romantic vacations, honeymoon escapes, and getaways! Located in Madeira Beach Yacht Club, a private gated community, free parking, high-speed WI-FI, TV cable, Netflix, 2 outdoor heated swimming pools, and fishing piers. Please, book at least 7 days before your arrival

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**

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.

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.

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.

Bayfront Escape | Heated Pool + Hot Tub
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

Stunning Gulf View/Balcony - 7th Floor @Johns Pass
$0 Cleaning Fee, $0 Airbnb Guest Service Fee – we cover this fee. What you see is what you pay! Stay in style at this top-floor Madeira Beach condo with breathtaking Gulf views! Just steps from the sand and John’s Pass Village, this modern retreat features an open layout, full kitchen, and private balcony for stunning sunsets. Enjoy resort-style amenities, nearby dining, shops, and nightlife for the ultimate coastal escape!
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Tootsie’s Beachside Retreat-New Heated Pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

[Guest Favourite] Family Fun Oasis | Heated Pool,

Ocean Dreaming: Waterfront Home with Heated Pool,

Piece of paradise in Indian Rocks Beach.

TropicalPOOL Oasis- 5 Minutes to Beach-Fun Decor!

Splash House - Relaxation Haven/Private Pool

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING
Apartment rentals with a pool

Great Value in Clearwater/ St. Pete Region!

Beach Front Gulf View at John’s Pass Medeira Beach

Beachfront Bliss | King Bed | Heated Pool + Views!

2/2 Newly remodeled Beach Front - Sunset Vistas

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Gulf front 1 BR condo-

A Coastal Haven steps from the beach and more!

The Seascape Premier Beachfront Cottage-Gulf View
Other holiday rentals with a pool

Modern Coastal Retreat

Luxury Penthouse Beach Condo

Beach-steps away! Waterfront Pool View!5

Stunning Waterfront Condo/Heated Pools/Near Beach

Ram Sea 203: Gulf Views & Poolside Vibes

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

Tranquil "Ocean Breeze Retreat"

Waterfront Oasis / Gameroom / Pool & Beach Access
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ₹15,571 | ₹19,441 | ₹23,581 | ₹19,711 | ₹17,911 | ₹18,631 | ₹18,541 | ₹16,471 | ₹15,841 | ₹14,400 | ₹14,400 | ₹15,121 |
| 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 ₹2,700 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
Destinations to explore
- Seminole Holiday rentals
- Central Florida Holiday rentals
- Miami Holiday rentals
- St Johns River Holiday rentals
- Orlando Holiday rentals
- Gold Coast Holiday rentals
- Miami Beach Holiday rentals
- Fort Lauderdale Holiday rentals
- Four Corners Holiday rentals
- Tampa Holiday rentals
- Kissimmee Holiday rentals
- Key West Holiday rentals
- Beachfront rentals Madeira Beach
- Townhouse rentals Madeira Beach
- Waterfront rentals Madeira Beach
- Rentals with a sauna Madeira Beach
- Serviced apartment rentals Madeira Beach
- Rentals with a washing machine and dryer Madeira Beach
- Rentals with an EV charger Madeira Beach
- Apartment rentals Madeira Beach
- Villa rentals Madeira Beach
- Pet-friendly rentals Madeira Beach
- Beach apartment rentals Madeira Beach
- Cottage rentals Madeira Beach
- Rentals with a patio Madeira Beach
- Family-friendly rentals Madeira Beach
- Beach house rentals Madeira Beach
- Bungalow rentals Madeira Beach
- Rentals with a firepit Madeira Beach
- Rentals with a kayak Madeira Beach
- Rentals with beach access Madeira Beach
- Rentals with a fireplace Madeira Beach
- Rentals with a hot tub Madeira Beach
- Flat rentals Madeira Beach
- House rentals Madeira Beach
- Rentals with outdoor seating Madeira Beach
- Hotel rooms Madeira Beach
- Fitness-friendly rentals Madeira Beach
- Rentals with pools Pinellas County
- Rentals with pools Florida
- Rentals with pools United States
- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
- Raymond James Stadium
- Turtle Beach
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Cortez Beach
- Lido Key Beach
- Anna Maria Public Beach
- Amalie Arena
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Gulfport Beach Recreation Area
- North Beach
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Adventure Island
- Honeymoon Island Beach
- Splash Harbour Water Park




