Madeira Beach


Properties Available 79 properties available
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons To Book: * Beachfront Property with Direct Access to the Beach* New and Beautiful Updates!* Watch Stunning Sunsets from your Private Balcony* Onsite Heat Pool and Hot Tub
Arie Dam 202
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (95 Reviews)
Top Reasons to Book:* Stunning Views from Private Balcony * Heated Beachfront Pool* Hot Tub * Beach Front* In-unit washer and dryer* Professionally Managed For a serene and rejuvenating vacation experience with unparalleled Gulf views and top-notch amenities, Surfside South 312 is the ideal choice. This two-bedroom, two-bathroom condo offers a perf
Surfside South #312
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
 New Property!
Top Reasons To Book John's Pass-Time #1:* Beachfront Property with Direct Beach Access* Ground Level Cottage, No Stairs Required* Large Private, Covered Deck with Table and Chairs* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #1, a charming and cozy
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



John's Pass-Time Beach Cottage #1
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.8 (5 Reviews)
Top Reasons To Book This Beachfront Condo:* Beautiful and Spacious Condo Directly on Madeira Beach* 3 Balconies - Main Balcony Overlooking the Beach and Gulf of Mexico* Onsite Heated Beachside Pool with Lounge Chairs * Direct Beach Access—Step Off the Pool Deck onto the Sand* Professionally Managed, 24/7Welcome to Trillium 2A, a beautiful and s
Trillium 2A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (91 Reviews)
Top Reasons to Book Trillium 3A: * Beachfront Condo with Amazing Views of Madeira Beach* Beautifully Updated Throughout - Stunning Condo!* Heated Pool and Pool Deck with Lounge Chairs* Smaller, Quaint Beachfront Building with Only 15 Units Total* Perfectly Situated on Madeira Beach - Close to John's Pass Village and Boardwalk* Professionally
Trillium 3A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (57 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
Trillium 5C - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (74 Reviews)
***POOL CLOSURE - THE POOL WILL BE CLOSED BEGINNING MAY 1ST, 2026 - MORE EXTENSIVE REPAIRS ARE REQUIRED AND CURRENTLY THERE IS NOT A SET REOPEN DATE - WE WILL REMOVE THIS NOTICE WHEN THE POOL HAS REOPENED. ****Top Reasons To Book This Condo:* Prime Location Directly across from John’s Pass Village and Boardwalk with Shops, Dining, and Entertainme
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



Madeira Norte 406 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
 New Property!
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated saltwater swimming pool du
Villa Madeira 506 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (43 Reviews)
Top Reasons To Book This Condo:* Right Across the Street From the Beach - Easy Access, 300ft!* Great Onsite Amenities: Heated Pool, Hot Tub, Pool Deck with Lounge Chairs, Workout Room* Modern, Updated Condo with Private Balcony* Great Location - Walk to John's Pass Village and Boardwalk* Professionally Managed, 24/7Welcome to Madeira Bay II #3
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



Madeira Bay Resort II - 314
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (6 Reviews)
Top Reasons to Book: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico.• Shared covered lounge chairs and access to the heated swimming pool during your visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. Stay more, SAVE more! We offer lower nightly rates on extended stays from
Specials Tag Special
Hot Summer Savings Are Here!


Enjoy 10% off your summer escape when you stay between June 2 and September 1, 2026. Book 3 nights or more and make the most of peak season for less.

Use code HOTDEALS at checkout.

*New online bookings only. Minimum stay required. Restrictions apply.



Villa Madeira 301 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (89 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to book: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
Trillium 5A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (77 Reviews)
Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just enter your dates, at least 14 nights, for pricing. Top Reasons to Book: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your vis
Villa Madeira 204 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (15 Reviews)

Tell us what you're looking for and someone will contact you with available options.

I agree