Madeira Beach
79 properties available
** NEW PHOTOS OF 2ND BEDROOM WITH KING BED COMING SOON **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 with brand new outdoor furniture featuring breathtaking views of the Gulf of Mex
Villa Madeira 402 - Premier
Condo
3
bedrooms
2
Full
6
guests
4.7
(16 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 vi
Villa Madeira 206
Condo
3
bedrooms
2
Full
6
guests
4.9
(61 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 visi
Villa Madeira 307 - Premier
Condo
3
bedrooms
2
Full
6
guests
4.9
(47 Reviews)
Top Reasons to Book This Home: * Quick and Easy Walk to Beach Access - Only 200ft Away!* Single Family Home to Yourself* Backyard Area with Gas Grill and Outdoor Dining Table* Spacious Open-Concept Living* Professionally ManagedWelcome to Sunset Paradise Home, your perfect beach getaway in Madeira Beach! Enjoy the entire single-family home to your
Sunset Paradise
House
2
bedrooms
1
Full, 1 Half
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 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
3
bedrooms
2
Full
6
guests
5
(43 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 visi
Villa Madeira 301 - Premier
Condo
3
bedrooms
2
Full
6
guests
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 vi
Villa Madeira 408 - Premier
Condo
3
bedrooms
2
Full
6
guests
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 PLUS the kitchen appliances have been recently replaced with gorgeous stainles
Trillium 1C - Premier
Condo
2
bedrooms
2
Full
6
guests
4.9
(61 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 505 - Premier
Condo
3
bedrooms
2
Full
6
guests
4.9
(75 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
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
2
bedrooms
2
Full
5
guests
5
(8 Reviews)
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 a panoramic view of the Gulf of Mexico. • Enjoy direct beach access as well as an outdoor heated pool! • Open floor plan with plenty of room for the entire family to
Trillium 2C - Premier
Condo
2
bedrooms
2
Full
6
guests
4.9
(74 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 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
5
bedrooms
4
Full
12
guests
5
(14 Reviews)
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