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 this NEW Townhome: * Just Built and Everything is New! - 2025* Easy Walk to Madeira Beach, Approx. 300ft* Private Rooftop Deck with Seating - Great Hangout Spot!
Azul Townhomes A3 - Sunrise
Townhouse
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 12 guests
Rating 5 (14 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. If you can vacation for a minimum of 1-month, this beautiful condo is t
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 208
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (8 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 the Sunrise and Sunset Townhomes: * 2 Townhomes Side by Side* Each Townhome is 4 Stories with a Private Roof Top Deck* Approx. 300ft to the Beach - Easy Walk!*
Azul Townhomes A3 and A4 - Sunrise/Sunset
Townhouse
Bedrooms 10 bedrooms
Bathrooms 8 Full
Guests 24 guests
Rating 5 (2 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: • 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 405 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (22 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 Madeira Del Mar 301:* Don’t forget your fur baby! This unit is dog friendly (restrictions and fees apply). * Onsite outdoor resort style pool (heated seasonally) wi
Madeira Del Mar 301
Condo Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (37 Reviews)
Top Reasons To Book John's Pass-Time #2:* Beachfront Property with Direct Beach Access* Gulf Views from your Private Balcony* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Great Location - Walk To John's Pass Village and Boardwalk* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #2, a peaceful 2-be
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 #2
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (12 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!
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)
**Please note that due to damage from the recent hurricanes the elevators may be in and out of service. **Top Reasons to Book this Beachfront Condo:* Beachfront Condo with Direct Views of the Gulf of Mexico* Open and Spacious Condo on 10th Floor* Large Pool Deck with Table and Chairs* Heated Pool, Hot Tub and Shuffleboard on Grounds * Central Locat
Ocean Sands 1-1002
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (13 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 202
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (118 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 balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your visit. • Loc
Villa Madeira 305
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (43 Reviews)

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