
Holiday 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.

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.

Welcome to Gulf-Front Paradise!
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

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**

Five Star Beachfront Condo Newly Renovated
A newly transformed beachfront Condo offers five-star accommodations in sleepy Indian Shores, Florida. This is the second renovated unit by a Superhost/owner. This unit is only feet from the beautiful white sand & crystal clear water. The sunsets are epic from the balcony. Several great restaurants & bars are within walking distance of your front door. Amenities include a fully stocked kitchen, heated pool, SmartTV's, high speed Wi-Fi, reserved parking and only minutes from the Tampa airport.

Private Beachfront 4BR 2BA Bungalow*Pool*PETS OK
PRIVATE BEACH OPEN! Barrett Beach Bungalows preserves the traditional Florida beach endearments in style with 4 charming beach bungalows. Why spend your Florida beach vacation in a busy hotel ? Stay in your own private bungalow! No crowded halls, elevators, lobby areas. Enjoy a vacation the way Florida was before the development boom. No waiting for crowded elevators! Direct on sandy beach with sparkling pool! All bungalows have modern amenities, are extra clean & beautifully decorated

Steps to beach with Marina Sunsets – 3 -Bed condo
Beautiful , New 3 bedroom Condo - directly across from the Beach . Gorgeous marina views from 2 of the 3 bedrooms . Walk straight to sugar-white sands, enjoy dinner on the patio overlooking boats — perfect for couples, families, or groups. Located next to John's Pass Village (Restaurants and Shops) . The condo features 2 full bathrooms and a pull out sofa and can accommodate up to 8 guests. WIFI , 3 smart TV's in the Unit. Washer/ dryer Free parking for one vehicle onsite

Beautiful Tampa Bay Pool Home Near Gulf Beaches
A beautiful Gulf Coast residence with many amenities to offer. Bright and open furnished spaces, for relaxing and entertaining up to 10 guests. A quiet, upscale neighborhood , your just 6 minutes from Madeira Beach and many other Gulf of Mexico beaches. Or, fun & sun in the private pool outback. 20 minutes from Downtown St Pete, which offers restaurants, museums, the new Pier, and excellent night life. Very close to countless restaurants, shopping, coffee shops, and grocery stores.

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.

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.

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

Tootsie’s Beachside Retreat-New Heated Pool

Pretty-n-PINK Mid Century Modern Home *

Insta Worthy Retreat -Arcade Room- Htd Pool- Golf

Oceanfront 3/2 with 180 degree view BOOK NOW!

Splash House - Relaxation Haven/Private Pool

Tranquil "Ocean Breeze Retreat"

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

Luxe BeachHouseA/Heated Pool/2 min walk to Beach
Apartment rentals with a pool

Oceanfront View, Spacious Townhouse, Heated Pool

Great Value in Clearwater/ St. Pete Region!

Florida Getaway~Picture Perfect Views~Pool & Bar

Beachfront building across from Johns Pass Village

Villa Madeira Stunning Beachfront Corner 3 Bedroom

Penthouse Mad Beach - Private Rooftop & 360 Views

Ocean View Perfect Oasis to Relax!

Pearl of the Sea, 1 BDRM, 2 min walk to the beach
Other holiday rentals with a pool

Modern Condo | Remodeled, Beach Access, Sleeps 6

Pool Home close to Indian Rocks Beach Pet Friendly

Sunset studio

Stunning Waterfront Condo/Heated Pools/Near Beach

Oceanfront Luxury paradise

White Sand Beachfront Condo with Stunning Sunsets

Coastal Haven | Heated Pool, 5-Min Beach Walk

Ocean Breeze Madeira Beach; steps from the beach
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $246 AUD | $307 AUD | $373 AUD | $311 AUD | $283 AUD | $294 AUD | $293 AUD | $260 AUD | $250 AUD | $262 AUD | $270 AUD | $282 AUD |
| 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 1,080 holiday rentals in Madeira Beach

Nightly prices starting at
Madeira Beach holiday rentals start at $43 AUD per night before taxes and fees

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

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

Pet-friendly holiday rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wifi availability
1,080 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
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- Anna Maria Island
- Siesta Beach
- Crescent Beach
- Raymond James Stadium
- Busch Gardens Tampa Bay
- John's Pass
- Turtle Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Dunedin Beach
- Amalie Arena
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- Anna Maria Public Beach
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- Tampa Palms Golf & Country Club
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- River Strand Golf and Country Club
- Hard Rock Casino
- North Beach At Fort DeSoto Park
- Splash Harbour Water Park
- Adventure Island
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