
Vacation rentals with a pool in Madeira Beach
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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.

Private Beach 2BR Bungalow *heated POOL* PETS ok
PRIVATE BEACH OPEN!!! ENJOY your own bungalow! (NOT a condo - no crowded elevators, hallways, lobby areas) Barrett Beach Bungalows preserves the traditional Florida beach endearments in style with 4 charming bungalows. Why spend your Florida vacation in a busy crowded hotel? DOLPHIN BUNGALOW is ONLY 50 steps to beach, sits behind beachfront bungalow but not beachfront. ALL Guests enjoy heated beachfront pool, lounge chairs, umbrellas, fire pit, volleyball, toys. Fully equipped, super clean!

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

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.

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**

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!

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.

*Shore Thing* Walk to Beach | Intercoastal Views
🏖️ Shore Thing Condo 🏖️ Experience the ultimate blend of Sunset Bliss at this stylish Treasure Island retreat. Just steps from powdery sands, ocean breezes and breathtaking sunsets. Keep an eye out for local wildlife as dolphins and manatees glide by. Inside, enjoy coastal vibes featuring modern beachy interiors. Whether you are preparing a meal in the luxury kitchen or diving into the intercoastal heated pool, my service ensures your comfort always comes first.

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.

Lovely-2 bedroom condo with 2 pools, Madeira beach
This centrally-located, friends and family friendly, condo on the water is a must stay! The most beautiful Gulf Coast beach sits right across the street. Beach access is a short walk from the gated Madeira Beach Yacht Club! Just 2 miles from the world famous Johns Pass full of shops, bars and dozens of different dining and late-night spots. This complex has 2 swimming pools, hot tub, gym, and is located on the intercoastal waterway. Your beach oasis awaits!

Penthouse,intercoastal, 3/3 views/heated pool
This stylish place to stay is perfect for group trips. Brand New Luxury Madeira Beach Penthouse With Heated Pool 4 floors up with partial beach and intercoastal views, all on a level floor plan 4 stories up with elevator access! Enjoy the comforts of new unit with modern appliances and fixtures in this 3/3 that bolsters a king master bedroom, two guest queen bedrooms all with in suite full bathrooms.
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

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

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

Stunning views! Spot dolphins from the pool!

The Blue Fin, 3 Bed/ Heated Pool/ XBOX

Redington Beach near beach on ICW w/pool & dock

UTOPIA!Heated Pool &Hot Tub 2 master suites w KING

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

Oceanfront View, Spacious Townhouse, Heated Pool

Modern Condo | Remodeled, Beach Access, Sleeps 6

Updated Beachfront Condo at Madeira Norte Unit 307

Chambre 102- Pool, Hot Tub, Walk to John's Pass!

Steps to beach with Marina Sunsets – 3 -Bed condo

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

Ideal beach getaway condo!

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

Madeira Beach Condo - Walk to Beach & Shopping! :)

Newly Renovated Condo on Madeira Beach!

Stunning Waterfront Condo/Heated Pools/Near Beach

Casa Brisa - Htd. Pool-Unique Bungalows-Hot Tub

Oceanfront Luxury paradise

Tranquil "Ocean Breeze Retreat"

Tranquil Bay: Waterfront Home w/ Heated Pool

Penthouse Mad Beach - Private Rooftop & 360 Views
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | ﺩ.ﺇ635 | ﺩ.ﺇ793 | ﺩ.ﺇ962 | ﺩ.ﺇ804 | ﺩ.ﺇ731 | ﺩ.ﺇ760 | ﺩ.ﺇ757 | ﺩ.ﺇ672 | ﺩ.ﺇ646 | ﺩ.ﺇ676 | ﺩ.ﺇ698 | ﺩ.ﺇ727 |
| 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 1,080 vacation rentals in Madeira Beach

Nightly prices starting at
Madeira Beach vacation rentals start at ﺩ.ﺇ110 per night before taxes and fees

Verified guest reviews
Over 26,130 verified reviews to help you choose

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

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wi-Fi availability
1,080 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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- Anna Maria Island
- Siesta Beach
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
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- Amalie Arena
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