
Vacation 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.

Waterside Studio in the heart of TI, walk to beach
Location!!! This charming 2nd floor studio is located in the heart of legendary Treasure Island on the Intracoastal waterway of Boca Ciega Bay, only 3-7 min walk from the beautiful Gulf beaches, restaurants, shopping, and many great beach bars. Relax in the heated pool, have a cookout with the grills and screened waterfront cabana, complete with TV and minifridge, and watch the sunset or fish on one of two docks as dolphins frolic in the warm Gulf waters around you! Your perfect vacation awaits!

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.

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.

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.

Waterfront studio! Heated pool and hottub
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 🏖️ ✨ 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 🌅 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.

Royal Orleans at Redington Beach ( Studio )
Royal Orleans 208 is a studio condo with one queen size bed that sleeps up to 2 . The condo is located on the second floor overlooking the (heated) pool . A super relaxing Gulf shore vacation that puts you just across from the beach, restaurants, and shops. In addition to the beautiful pool at Royal Orleans , you are close to golf and boating opportunities. It’s a recipe for a wonderful vacation in Redington Beach, Florida.

2 Bedroom 1 Bath Upstairs MODERN Apt NO PETS
Pools are open and wifi works great! Completely Renovated and Beautiful!2 Bedroom 1 Bathroom Upstairs unit w/t Full Kitchen. This unit sleeps 6 people. Sorry No Pets Allowed. Each bedroom has a queen size bed and the sofa turns into a queen bed as well. Watch a Movie on the 70" TV in the Living Room or Play a Game on the PlayStation 4! Or Retreat to one of the 2 bedrooms each with a 55" TV. Full Kitchen includes Stove

Beach Front Madeira Beach
Amazing beachfront condo, newly remodeled on the second floor. Vinyl plank flooring throughout, No CARPET. 2 Bedroom, 2 Bath. Completely unobstructed views of the beach. It is centrally located less than 1 mile from World Famous Johns Pass. Enjoy breathtaking sunsets from your living room with the water just feet away. The condo is walking distance to shopping, banking and many restaurants and bars.
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Hibernate in our Bear Creek Home

Tootsie’s Beachside Retreat-New Heated Pool

Beautiful Tampa Bay Pool Home Near Gulf Beaches

Modern Cozy 3BR | Walk to IRB Beach + Heated Pool

Pool Home with 2 King Beds | Relaxing Getaways

Surf’s UP! Pool, Cabana & Poolside bungalow!

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

Mad Beach HideAway • Private Pool • 4 Bed • 3 Bath
Condo rentals with a pool

Updated Beachfront Condo at Madeira Norte Unit 307

Chambre 103- Beachfront, Pool, Hot Tub,Johns Pass!

Beachfront building across from Johns Pass Village

Steps to beach with Marina Sunsets – 3 -Bed condo

Perfect Ocean Sunset view Madeira Beach/Johns Pass

PRICELESS VIEW Boca Ciega Bay Condo 1/1 #209

1br Condo with Pool and Palms View & Beach Access

Ocean Breeze Madeira Beach; steps from the beach
Other vacation rentals with a pool

Beach-steps away! Waterfront Pool View!5

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

Sunset Sanctuary | Heated Waterfront Pool + Dock

White Sand Beachfront Condo with Stunning Sunsets

Beachfront with Oceanview Balcony in Quiet Area

Bantasy Island

Tranquil "Ocean Breeze Retreat"

Upscale, cozy and coastal condo!
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $236 CAD | $295 CAD | $358 CAD | $299 CAD | $272 CAD | $283 CAD | $281 CAD | $250 CAD | $240 CAD | $251 CAD | $260 CAD | $270 CAD |
| 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 $41 CAD 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 and kid-friendly amenities

Pet-friendly vacation rentals
Find 90 rentals that welcome pets

Rentals with dedicated workspaces
740 properties have a dedicated workspace

Wifi availability
1,080 of Madeira Beach vacation 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
- Dunedin Beach
- Coquina Beach
- Vinoy Park
- Lido Key Beach
- Amalie Arena
- Cortez Beach
- Anna Maria Public Beach
- Bean Point Beach
- Jannus Live
- ZooTampa at Lowry Park
- Tampa Palms Golf & Country Club
- River Strand Golf and Country Club
- Gulfport Beach Recreation Area
- Adventure Island
- Busch Gardens
- Splash Harbour Water Park
- North Beach At Fort DeSoto Park




