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

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

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

Verified guest reviews
Over 27,740 verified reviews to help you choose

Family-friendly holiday rentals
960 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 120 rentals that welcome pets

Rentals with dedicated workspaces
830 properties have a dedicated workspace

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

Perfect Ocean Sunset view Madeira Beach/Johns Pass
Excellent location for families or couples traveling to the beach! The building is BRAND NEW in late 2020. Beautiful private condo, a great view of the Gulf with perfect sunsets from the 6th-floor balcony. Master bedroom with an excellent view of the beach from bed. Steps away are the beach and John's Pass shopping district-with excellent restaurants and shopping. King size master with private en-suite bath. Private covered parking in attached garage. Heated pool with baja shelf and hot tub.

Beach Front at “The Shore”
Welcome to The Shore —a beautifully renovated beachfront retreat in the heart of Madeira Beach. This second-floor 2-bedroom, 2-bath condo offers completely unobstructed Gulf views and the rare feeling of being almost directly on the water. Relax with your morning coffee in the signature blue chairs, watch breathtaking sunsets from the living room, and enjoy easy access to John’s Pass, waterfront dining, shopping, and the best of Gulf Coast beach living, where the shoreline feels just feet away.

Ocean View Perfect Oasis to Relax!
Ocean View! Newly renovated kitchen and bathroom! Just steps from the white sands of Madeira Beach shores. Kitchen is well equip with all you need to prepare your own meals, or go for a short stroll to many wonderful food options. Enjoy your coffee on the front porch with a view of the surf, or go for an early morning stroll on the beach. There is a pavilion and grill by the pool you are welcome to use. You will hear construction work while units all around are rebuilding from hurricane damage

Heated Pool! Huge Walk In Shower! 5 min to beach!
Welcome to Coastal Paradise! This modern villa is newly remodelled and professionally furnished with a beautiful coastal theme. It has a very spacious open layout with plenty of space for the whole family. A huge master walk in shower with two shower heads and four body jets! Out back is a private heated pool with lounge chairs, grill, a hammock, corn hole and a beautiful patio set to enjoy a meal outdoors. Madeira beach is only a 5 min drive away! We also provide all your beach necessities!!

Gulf View Penthouse | Steps to Beach + Johns Pass
Your Penthouse Paradise awaits at our Gorgeous, 7th-floor Gulf-View Condo in the new Madeira Bay Resort! Enjoy sweeping views of the beach, Gulf of Mexico, & miles of pristine coastline. Just steps from the sand & 1 block from John’s Pass Village & Boardwalk. Walk to dining, shopping, bars, & water sports. Come experience the best of Madeira Beach & make unforgettable memories in our newly furnished, well-stocked, luxury retreat w/all the comforts of home. Perfect for groups or families alike.

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**

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.

Luxury Seashell Oceanfront Condo with Pool
Book your next beach vacation at the stunning Seashell Condo in the Treasure Island Beach community. This modern and airy 2-bedroom, 2-bathroom vacation rental is the perfect getaway for relaxation and adventure. Enjoy the private terrace and chef's kitchen, as well as access to the shared pool, hot tub, gym, and rooftop terrace. Located just steps away from the beach and surrounded by fantastic restaurants and shops, Seashell Condo is the perfect place to call home during your beach vacation.

Beachfront Getaway with Resort-Style Pool
🌴 Escape to your own slice of beachfront paradise at Madeira Beach. This cozy 1BR studio features two queen beds, a private patio overlooking the ocean, and direct beach access just steps away. This unit is located on the 1st floor of the building. Elevator access is available. Enjoy a fully equipped kitchen, fast WiFi, and access to a pool and BBQ grill. With free parking and everything you need to relax and unwind, it’s the perfect getaway for couples, friends, or small families.

Luxury Home N/Heated Pool/Rooftop/Steps to Beach
New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome with heated salt water POOL located near a canal and the gulf just two blocks from the beach. Please note the pool is shared with the other side of the duplex. You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to the beach, restaurants, and volleyball. Close to Johns Pass, 2 miles. Please ask for the golf cart availability and a fee.

The Diving Dolphin
Welcome to our gorgeous gated waterfront resort! Immerse yourself in coastal luxury with a private boat slip, two heated pools, bikes included, ect. Steps away from pristine white sand Gulf beaches, the best dining and drinks, multiple excursion opportunities at your fingertips and Johns Pass minutes away. The convenience of stores nearby ensures you can enjoy your stay with no hassle. Everything you need is at the condo Indulge in the ultimate experience by the coast!

*Shore Thing* Walk to Beach | Intercoastal Views
🏖️ Shore Thing Condo 🏖️ Escape to pure coastal paradise at this chic Treasure Island condo. You are mere footsteps from sugar-sand beaches, refreshing salt air, and unmatched sunsets. Keep an eye on the water as dolphins and manatees drift right by! 🐬🌅 Indoors, unwind in elevated, modern coastal design. From cooking in the upscale kitchen to swimming in the heated pool, our signature service guarantees your peace of mind is the top priority. Book today! ✨🐚
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Red Key Beach | Redington Beach Heated Pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Blue Lagoon | Private Pool & Walk to the beach

Casa Flamingo - Private - Outdoor Bar+TV - Games

Oceanfront 3/2 with 180 degree view BOOK NOW!

Sandy Morning Restored | Pool Spa

Stunning views! Spot dolphins from the pool!

Lux Spa Retreat•Pool•Hot Tub•Sauna•10 min to Beach
Apartment rentals with a pool

Luxury Penthouse Beach Condo

COASTAL CHIC! Luxury Apartment with Oceanviews

Penthouse,intercoastal, 3/3 views/heated pool

Rincón Divino MB 2 Balconies, Ocean & Marina Views

Luxury Beach Condo - 3BR/3BA

Waterfront Treasure Island Resort Heated Pool

Coastal Haven | Heated Pool, 5-Min Beach Walk

Five Star Beachfront Condo Newly Renovated
Other holiday rentals with a pool

Modern Condo | Remodeled, Beach Access, Sleeps 6

Sandy Shores #204 - John's Pass, Pool, Gulf front!

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

The Mad Pearl

Sunset Sanctuary | Heated Waterfront Pool + Dock

The Harbor Condo Beach Escape!

Oceanfront Luxury paradise

Beach Front, Ocean & Gulf views ~ Las Brisas 506.
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | €180 | €218 | €260 | €192 | €174 | €181 | €180 | €160 | €154 | €161 | €166 | €173 |
| 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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