Madeira Beach holiday rentals

We found 8,957 holiday rentals — enter your dates for availability

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October 2025

November 2025

Discover a selection of 118 homes, 104 apartments and other holiday rentals in Madeira Beach that are perfect for your trip. Holiday homes provide the best amenities for your family, friends or furry companion, such as cable TV and a washer and dryer. Whatever you're looking for, you'll find a property to rent that has what everyone needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts - Madeira Beach

Showing deals for:9 Jan - 16 Jan

Wonderful

(41 reviews)

🌅 Madeira Bay Resort #408 – Stylish Marina-View Condo with Updated Décor & Gulfside Charm

Madeira Beach, FL

5% off

for 7 nights, 1 apartment

AU$352 per night

includes taxes & fees

Panoramic water views with an oversized sliding glass door in the living room

Exceptional

(41 reviews)

Exclusive PENTHOUSE Footsteps from Madeira Beach! 3BR/3BA with a Heated Pool!

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$660 per night

includes taxes & fees

Enjoy bayside water views from your private screened in lanai.

Exceptional

(5 reviews)

Enjoy sunny water views from your private lanai. Steps to Madeira Beach.

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$288 per night

includes taxes & fees

Madeira Norte. Direct Gulf Front Property.

Exceptional

(10 reviews)

Beachfront Bliss - King Bed - Heated Pool - Steps to John’s Pass & Dining!

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$540 per night

includes taxes & fees

Excellent

(32 reviews)

🐾 Madeira Bay Resort I #1701 – Spacious 3-Bedroom Retreat Near the Beach & John's Pass

Madeira Beach, FL

7% off

for 7 nights, 1 apartment

AU$512 per night

includes taxes & fees

Exceptional

(89 reviews)

Look no further!! Beachfront Condo in Paradise, Short walk to John's Pass.

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$794 per night

includes taxes & fees

Exceptional

(123 reviews)

Stunning beach views from balcony in upscale BEACHFRONT condo with pool and spa

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$616 per night

includes taxes & fees

Very good

(91 reviews)

GULF FRONT BEACH CONDO SUMMER SPECIALS Stunning Balcony Beachfront POOL SUNSETS

Madeira Beach, FL

7% off

for 7 nights, 1 apartment

AU$434 per night

includes taxes & fees

Spectacular view of beach and Gulf from the balcony - all that's missing is you!

Exceptional

(162 reviews)

Listen to the Waves - Direct Gulf Front - WiFi, Parking Included

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$700 per night

includes taxes & fees

Exceptional

(41 reviews)

Madeira Bay Resort 311 condo sleeps 7 with All Resort Amenities

Madeira Beach, FL

7% off

for 7 nights, 1 apartment

AU$401 per night

includes taxes & fees

WALKING DISTANCE TO MADEIRA BEACH ACCESS: 0.2 MILES AWAY.

Exceptional

(6 reviews)

!LAST MINUTE PROMOTION!HEATED POOL&SPA-BRAND NEW-CONDO-WALK TO BEACH/SHOPS/CAFES

Madeira Beach, FL

5% off

for 7 nights, 1 apartment

AU$516 per night

includes taxes & fees

Exceptional

(10 reviews)

Madeira Beach1 Waterfront & 2-3 minutes' Walk to the Beach

Madeira Beach, FL

6% off

for 7 nights, 1 apartment

AU$412 per night

includes taxes & fees

Excellent

(19 reviews)

Madeira Beach Yacht Club - best King Size Bedroom and 2min walk to beach and...

Madeira Beach, FL

7% off

for 7 nights, 1 apartment

AU$296 per night

includes taxes & fees

Exceptional

(35 reviews)

Beautiful Madeira Yacht Club Beach Condo-1BR/ 1.5BA. Sleeps 4 comfortably!

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$400 per night

includes taxes & fees

Wonderful

(94 reviews)

Newly reduced FALL rates: 1bd 1ba Gulf front: Ktchn, Pool, + John's Pass access!

Madeira Beach, FL

8% off

for 7 nights, 1 apartment

AU$407 per night

includes taxes & fees

Find spaces that suit your style

House

Condo/Apartment

Find properties near top attractions in Madeira Beach

John's Pass Village & Boardwalk

Find the best place to stay - Madeira Beach

John's Pass Hotel

Sleeps 8 · 3 bedrooms

View from the Living Room of the Gulf of Mexico & white sands of Madeira Beach.

Premier Host

Beach View, Private Plunge Pool, Charming 1938 Bungalow Madeira Beach Johns Pass

Sleeps 8 · 3 bedrooms · 2 bathrooms

Peace of mind
Our Book with Confidence Guarantee gives you 24/7 support
More quality time
From booking to staying, the whole process is simple and enjoyable
All the privacy of home
Enjoy full kitchens, laundry, pools, gardens and more
More for less
More space, more privacy, more amenities — more value

Delight in the beachside landscape of Madeira Beach

The beaches and other outdoor surroundings create an inviting atmosphere in Madeira Beach. Well known for its seafood restaurants, surfing and dolphin watching, this walkable city won't disappoint. John's Pass Village & Boardwalk and Tampa Bay are just a couple of the must-see attractions in the area. With a holiday rental, you get a home away from home – many rentals offer full kitchens and outdoor grills for some home cooking.

Activities and attractions in and around Madeira Beach

Are you hoping to discover attractions to visit in the area? Travellers enjoy fun activities like dolphin viewing and fishing. Although it can be tempting to stay in your comfortable holiday rental, you'll want to experience everything that Madeira Beach has to offer. Here are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

Splash Island Water Park (5.7 mi / 9.2 km)
Splash Harbour Water Park (6.6 mi / 10.6 km)
Tampa Bay Grand Prix (8.6 mi / 13.9 km)
Renaissance Vinoy Golf Club (10.6 mi / 17 km)
St. Pete Pier (10.7 mi / 17.2 km)
Celebration Station (14.2 mi / 22.9 km)

Exploring the beaches and other natural features in Madeira Beach

Travellers enjoy Madeira Beach for its sunsets and seaside. Whether you're looking for adventure or just want to appreciate the scenery, Madeira Beach is a great place to spend some time outside. Here are a few of the area's most eye-catching natural features, all within 30 miles (48.2 km) of the city centre:

Tampa Bay (15.7 mi / 25.3 km)
St. Petersburg Municipal Beach (2.7 mi / 4.3 km)
Sunset Beach (4.2 mi / 6.8 km)
Upham Beach Park (5.2 mi / 8.3 km)
Upham Beach (5.2 mi / 8.3 km)
Pass-a-Grille Beach (5.6 mi / 9 km)

Seasonal weather averages in Madeira Beach

If you're hoping to enjoy some warm-weather activities on your holiday, August, July, September and June are the hottest months to visit, when temperatures average 28°C.

Transport to and around Madeira Beach

The nearest airport is in St. Petersburg, FL (PIE-St. Petersburg-Clearwater Intl.), located 9.9 mi (16 km) from the city centre. If you can't find a flight that's convenient for your trip, you could also fly into St. Petersburg, FL (SPG-Albert Whitted), which is 10.3 mi (16.6 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Madeira Beach?

Condos are the most popular style of holiday home in Madeira Beach, according to our data. Even if you have a different idea about what you'd like, Stayz has properties in a variety of shapes and sizes. Filter our options to find your ideal match.

How much does it cost to rent a holiday home in Madeira Beach?

Different things affect what you'll pay for your holiday home in Madeira Beach, like the type of property, length of stay and season. However, all Stayz homes have one thing in common — amazing value. Just add your travel dates to find your ideal match.

How much does it cost to rent a beach house in Madeira Beach?

When you travel and the size and style of the property will influence how much you'll pay for your beachside stay. Click on your Madeira Beach travel dates to view your options on Stayz. Looking for basics like WiFi, or perks like a private pool? Use the filters to choose the features and amenities you need.

Are there pet-friendly holiday homes in Madeira Beach?

With 247 properties that host four-legged guests, your furry best friend can also come along on your Madeira Beach break. Use our filter tool to search our pet-friendly holiday homes and find a holiday home that'll set tails wagging on Stayz.

Can I rent a house with a pool in Madeira Beach?

Add a whole new level of fun to your trip by booking one of the 215 houses with a private pool in Madeira Beach. Use our search filter to find properties with pools on Stayz, then spend carefree days splashing around in a swimming pool that's all your own.

What are popular home amenities in Madeira Beach?

When it comes to home amenities that people are looking for in Madeira Beach, a swimming pool, a garden and an ocean view rank the highest. With Stayz holiday homes, you'll find options to suit your taste and style, whether you're going away with family members, friends or even pets.

Are there large group holiday homes in Madeira Beach?

You'll discover three holiday homes in Madeira Beach that can host 10 or more people. Whether you're organising a get-together with extended family or a special event, there's plenty of room to get your favourite people together under one roof.

Are there holiday homes in Madeira Beach that welcome kids?

Madeira Beach has 247 family-friendly holiday homes. And tracking down a stay that welcomes kiddos is a cinch with Stayz's "Properties good for families" filter. As well as having the whole place to yourselves, you'll get perks and amenities like dining rooms, full kitchens and yards.

What are the top attractions for families in Madeira Beach?

Keep the kids busy at these fabulous family-friendly attractions in Madeira Beach:

Splash Harbour Water Park
Upham Beach
Pass-a-Grille Beach

Are there one-bedroom holiday homes in Madeira Beach?

Yes, you'll find 56 one-bedroom properties in Madeira Beach to select from. A one-bedroom holiday home is a great choice if it's only you and your partner or if you're holidaying alone. Toss in more space, convenience and privacy than a standard hotel, and you've got the makings of a memorable getaway.

Can I find two-bedroom holiday homes in Madeira Beach?

Gather your nearest and dearest and experience complete comfort and privacy in one of the 142 two-bedroom holiday properties Madeira Beach has to offer.

Are there holiday homes with WiFi in Madeira Beach?

Whether you'd like to stay in touch with the news, send a few emails or surf social networks, there are 62 holiday homes with WiFi in Madeira Beach. Check the "WiFi" box when searching on Stayz and stay connected on your holiday.

How can I find holiday homes with air conditioning in Madeira Beach?

Decide on your travel dates and then use the filters to find holiday homes with air conditioning in Madeira Beach on Stayz. With 244 air-conditioned properties on offer here, you can look forward to a comfy and cool stay.

How old do you have to be to rent a holiday home in Madeira Beach?

It's a good idea to check with the Madeira Beach holiday home you want on Stayz as the age limit differs. However, it's normally 16, 18 or 21.

How long can I rent a holiday home in Madeira Beach for?

The amount of time you can book a Madeira Beach holiday home for differs depending on the property. Just enter your preferred travel dates to find options that offer extended stays. They come with the things you need to make your extended getaway more enjoyable such as air conditioning and kitchens. Some Stayz holiday properties may also offer weekly or monthly discounts, so you can stay longer for less money.