
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.

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.

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.

1Q Pet Friendly 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.

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!

"Jewel At The Shores" Gulf Front, sleeps 5
"Jewel at the shore"feels like you are in a snug resting place, your own nest, very homey with a breath taking Gulf view from the balcony. The gulf is right outside your door along with a year round heated pool, great on cool winter days. The unit is stocked with things you’ll need; linens, towels, shampoo et., necessities for the beach, keurig and drip coffee, some pods to get you started. New balcony and sliders. Just beautiful and comfy

Beach Home Luxury Heated POOL-Golf Cart (S)
Vista Luxury Vacation Rentals Brand New, 2000 sq ft/3 Bedroom/3 Full Bathrooms 2 living rooms/modern townhome located near a canal and the gulf just two blocks from the beach. Heated salt water pool! GOLF CART!!! Ask for availability. (The cart has a small fee). You can enjoy full view of the canal and partial views of the gulf from the balconies and the rooftop! Walking distance to beach, restaurants, volleyball. Close to Johns Pass, 2 miles.

Beachfront Condo w/ Ocean View - Newly Renovated!
Newly renovated, 4th floor beachfront condo with a private balcony overlooking the gulf on Treasure Island Beach within walking distance to beaches, onsite pool, bars, and restaurants. View the sunset from your condo where you can relax in a queen size bed, full size sofa bed, and single fold up cot. Inside is a combo living/dining area and fully equipped kitchen, surrounded by beautiful furnishings and art.

Indian Shores Beach Getaway
Amazing two bedroom, two bath condo that is steps away (literally a 2 minute walk) from the beach and the intracoastal community fishing pier and heated swimming pool! Open floor plan boasts amazing views from the private , top floor balcony of protected conservation area and intracoastal waterway. Indian Shores is a wonderful coastal community we're happy to call our 2nd home!
Popular amenities for Madeira Beach rentals with a pool
House rentals with a pool

Heated Pool 4 bed 6.9 miles to Honeymoon Island.

Hibernate in our Bear Creek Home

The Palm House | Free Heated Pool!

Waterfront Coastal Bliss at Brightwater w/ Heated

Heated Pool Oasis • 5 min to Beach • Sleeps 11

Heated Pool no xtra chrge/Hot Tub 0.7 mi to Beach

Resort Home + Pink Bungalow & 7-Hole Putting Green

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

New! Modern Madeira Condo- Walkable to Beach, and

Paradise II

Lux Condo w/ 2 balconies, Ocean & Marina views

Beachfront balcony view heated pool hot tub

Newly Renovated Condo on Madeira Beach!

Best of the Gulf with a View - Sand Castle 1

High-n-dry, 2nd story, new AC, wifi. The Dolphin.

Penthouse Mad Beach - Private Rooftop & 360 Views
Other vacation rentals with a pool

Treasure Island Gem | Waterfront Heated Pool, Dock

Backyard Oasis! Fully remodelled! 4 min to beach!

The Harbor Condo Beach Escape!

Three Palms

Bantasy Island

Coastal Haven | Heated Pool, 5-Min Beach Walk

Tranquil "Ocean Breeze Retreat"

Newly Renovated Condo with Pool
When is the best time to visit Madeira Beach?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sep | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $240 CAD | $299 CAD | $363 CAD | $303 CAD | $276 CAD | $287 CAD | $285 CAD | $254 CAD | $244 CAD | $255 CAD | $263 CAD | $274 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 $42 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
- Raymond James Stadium
- Crescent Beach
- Busch Gardens Tampa Bay
- John's Pass
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