Luxury Vacation Rentals with a Private Pool in Madeira Beach

Luxury Vacation Rentals with a Private Pool in Madeira Beach

Never book a bad vacation home again. Every Wander comes with hotel-grade amenities, inspiring views, pristine cleaning and 24/7 concierge service.
We found 5 private pool vacation rentals – enter your dates for availability.

Top-rated private pool vacation rentals in Madeira Beach

Beautiful Waterfront House with Pool & Dock Access Close to Beach & Restaurants property photo 1

Beautiful Waterfront House with Pool & Dock Access Close to Beach & Restaurants

3 bedrooms•2 baths
Sonnenhaus 2 Blocks from Beach Access property photo 1

Sonnenhaus 2 Blocks from Beach Access

4 bedrooms•2 baths
972 US dollars for 2 nights•

~$80 less than other sites

Summer Special Waived Resort Fee Your Family Vacation Awaits at Madeira Beach Yacht Club property photo 1

Summer Special Waived Resort Fee Your Family Vacation Awaits at Madeira Beach Yacht Club

2 bedrooms•2 baths
1,009 US dollars for 5 nights•

~$90 less than other sites

Perfect Family Getaway with Pool in Madeira Beach 1 Block to Beach Access and Restaurants property photo 1

Perfect Family Getaway with Pool in Madeira Beach 1 Block to Beach Access and Restaurants

3 bedrooms•1 bath
22,435 US dollars for 89 nights•

~$1,995 less than other sites

Oceanview Oasis w/ Balcony, Steps to the Sand property photo 1

Oceanview Oasis w/ Balcony, Steps to the Sand

1 bedroom•2 baths
356 US dollars for 1 night•

~$25 less than other sites

Welcome to private poolside luxury in Madeira Beach

Welcome to private poolside luxury in Madeira Beach

Make your break unforgettable with Wander’s collection of luxury private-pool vacation rentals in Madeira Beach. Each home is professionally managed and pristine, blending hotel-level consistency with the space and privacy of a coastal retreat.
Think sunlit living rooms, chef-ready kitchens, fast WiFi for work and play, and your own private pool for lazy afternoons or moonlit dips. With premium linens, thoughtful design, and 24/7 concierge, our Madeira Beach homes deliver the effortless stay you’ve been looking for. Every detail is considered so you can settle in and feel at home the moment you arrive.

Available soon in Madeira Beach

Oceanview Oasis w/ Balcony, Steps to the Sand property photo 1

Oceanview Oasis w/ Balcony, Steps to the Sand

1 bedroom•2 baths
356 US dollars for 1 night•

~$25 less than other sites

All homes in Madeira Beach

Beautiful Waterfront House with Pool & Dock Access Close to Beach & Restaurants property photo 1

Beautiful Waterfront House with Pool & Dock Access Close to Beach & Restaurants

3 bedrooms•2 baths
Sonnenhaus 2 Blocks from Beach Access property photo 1

Sonnenhaus 2 Blocks from Beach Access

4 bedrooms•2 baths
972 US dollars for 2 nights•

~$80 less than other sites

Summer Special Waived Resort Fee Your Family Vacation Awaits at Madeira Beach Yacht Club property photo 1

Summer Special Waived Resort Fee Your Family Vacation Awaits at Madeira Beach Yacht Club

2 bedrooms•2 baths
1,009 US dollars for 5 nights•

~$90 less than other sites

Perfect Family Getaway with Pool in Madeira Beach 1 Block to Beach Access and Restaurants property photo 1

Perfect Family Getaway with Pool in Madeira Beach 1 Block to Beach Access and Restaurants

3 bedrooms•1 bath
22,435 US dollars for 89 nights•

~$1,995 less than other sites

Oceanview Oasis w/ Balcony, Steps to the Sand property photo 1

Oceanview Oasis w/ Balcony, Steps to the Sand

1 bedroom•2 baths
356 US dollars for 1 night•

~$25 less than other sites

View all homes

Highlights in Madeira Beach

Discover a sun-drenched Gulf Coast getaway filled with pristine sandy beaches, lively boardwalk shopping, and endless waterfront adventures.
John's Pass Village & Boardwalk
Archibald Beach Park
Hubbard's Marina
Alligator Attraction & Wildlife Learning Center
Smugglers Cove Adventure Golf
R.O.C. Park

IT'S A VACATION HOME, BUT BETTER

The Wander difference

Wander is different because we combine the quality of a luxury hotel with the comfort of a private vacation home. Your best trip ever is just a few clicks away.

Only the best homes

We’ll never not look like the pictures. Every Wander is beautiful and expertly operated, so you can leave any stress at the door.

Hotel-grade amenities

We’ll never leave you with nothing to do. From ultra fast WiFi to gyms and pools, our homes make it easy to blend work and play.

24/7 concierge service

We’ll never leave you hanging. Our chat-based Concierge is always available to help – from trip questions to special requests.

Inspiring and stunning views

We’ll never leave you uninspired. Every Wander has stunning views to refresh and inspire your soul. Adventure awaits.

Meticulous cleaning

We’ll never have you check in to a dirty house. Our cleaning teams are meticulous, and there are no chores at checkout.

Safety and security

We’ll never pass you off to a stranger. Every Wander location meets our industry-leading safety standards to give you peace of mind.

Most popular amenities for private pool vacation rentals in Madeira Beach

Outdoor pool (5)
Boat dock (1)
Heated pool (1)
Waterfront (1)
Gym (1)
Beach access (4)
Beach essentials (4)
Bicycle (1)
Patio (4)
Balcony (4)
Dryer (5)
Garden (3)
Fire pit (1)
Washer (5)
Ceiling fan (5)
Oven (5)

More popular private pool destinations near Madeira Beach

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Other popular amenities & vacation types in Madeira Beach

Family vacation rentals in Madeira Beach
Pet-friendly vacation rentals in Madeira Beach
Hot tub vacation rentals in Madeira Beach
Discover more beyond the pool in Madeira Beach

Discover more beyond the pool in Madeira Beach

Set on a barrier island between the Gulf of Mexico and Boca Ciega Bay, Madeira Beach features two and a half miles of sugar-white shoreline and gentle surf that invites all-day unwinding. Sunsets glow in vivid color, and early mornings are perfect for quiet walks along soft, shell-flecked sands.
John’s Pass Village & Boardwalk brings lively energy at the south end with charter boats, dolphin cruises, and waterfront views. Paddle calm bay waters, head offshore for fishing, or simply sink into the rhythm of beach life. This easygoing Gulf setting makes Madeira Beach a standout choice, which is why Wander’s luxury private-pool vacation rentals in Madeira Beach are the perfect choice, whether you’re traveling for work or leisure.

FAQs: Vacation Rentals in Madeira Beach

Why should I book a Wander in Madeira Beach over other private pool vacation rentals?

Wander offers a level of consistency and quality you won’t find with most private pool vacation rentals.
Every home in Madeira Beach delivers the quality of a luxury hotel, paired with the comfort and space of a private vacation home. You get hotel-grade amenities, meticulous cleaning, stunning views, and 24/7 concierge support in every stay. Why would you want to stay anywhere else?

Which are Wander’s most popular private pool vacation rentals in Madeira Beach?

Some of our most popular private pool vacation rentals in Madeira Beach include Beautiful Waterfront House with Pool & Dock Access! Close to Beach & Restaurants!, Sonnenhaus! 2 Blocks from Beach Access!, and Summer Special! Waived Resort Fee! Your Family Vacation Awaits at Madeira Beach Yacht Club!. Guests love the quality of a luxury hotel, the comfort of a private vacation home, and the consistently exceptional experience Wander is known for. Explore the full collection to find the perfect home for your next stay.

How many different private pool vacation rentals does Wander have available in Madeira Beach?

Wander offers 5 private pool vacation rentals in Madeira Beach, each carefully designed and expertly operated. Browse the full collection to see what’s available for your trip.

What time is check-in and check-out at Wander’s private pool vacation rentals in Madeira Beach?

You can check-in to Wander private pool vacation rentals in Madeira Beach after 4.00pm and check-out before 10.00am.

Do Wander’s private pool vacation rentals in Madeira Beach have WiFi access?

Yes. Every Wander home in Madeira Beach has ultra fast, reliable WiFi so you can stay connected throughout your stay.

What is Wander’s cancellation policy?

You can cancel your reservation within 24 hours of booking for a full refund.
For stays of less than 15 nights, you can cancel or reschedule up to 14 days before check-in for a full refund. For stays of 15 nights or longer, the cancellation window is 60 days.
For some homes, a 30-day deadline applies; this will be clearly shown before you book.