Shores of Madeira
410 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 Condo:* Location, Location, Location: Next to John's Pass and directly across from the sugar sand beach, with safe access via the pedestrian crosswalk light.*
Madeira Bay Resort I 1505
Condo
2
bedrooms
2
Full
6
guests
4.9
(104 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. *** CONSTRUCTION NOTICE: Crystal Palms is currently undergoing a restoration project (entire building) and work will be taking place on grounds, noise will be associated with this. There
Crystal Palms 201
Condo
2
bedrooms
2
Full
4
guests
4.9
(38 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 Friendly Native 204: * Quick and Easy Walk to Beautiful Upham Beach (about 500ft)* Cute, Quaint Condo in Low-Density Complex* Walking Distance to Restaurants, Beach
Friendly Native 204
Condo
2
bedrooms
1
Full
6
guests
5
(11 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: * Beach access directly across the street as well as on site fishing and charter boats. * Gym Available (Building II) * Short stroll away from many shops and resta
Madeira Bay Resort I 1502
Condo
2
bedrooms
2
Full
6
guests
4.9
(47 Reviews)
** THE POOL IS CURRENTLY CLOSED FOR MAINTENANCE. There may be noise onsite while restoration work is ongoing. **Top reasons to book Sea You at the Beach at Holiday Villas III: • Best of both worlds! Gorgeous sunrises from your private balcony, famous sunsets in your back yard• Onsite amenities include an outdoor heated pool, a community grilli
Holiday Villas III #109 - Sea You at the Beach
Condo
1
bedrooms
1
Full
2
guests
5
(14 Reviews)
****NOTICE OF ROOF WORK - BUILDING 6. ROOF WORK WILL BEGIN MARCH 30TH 2026 FOR APPROX 6 WEEKS. *** Top Reasons to book : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleyball, Tennis and Pickleball Courts. • Located on the peninsula, th
Land's End 6-302 Beach Front - Premier
Condo
2
bedrooms
2
Full
4
guests
5
(27 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 Beachfront Condo: * Private Balcony Overlooking the Beach and Gulf of Mexico * Short proximity to the onsite heated pool. * All the fabulous amenities includi
Land's End 7-204 Beach Front
Condo
2
bedrooms
2
Full
6
guests
5
(35 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: • Direct panoramic beachfront views from your large private balcony. • Onsite outdoor amenities in paradise include a beautiful, heated pool, tiki huts, BBQ Grills
Las Brisas 202
Condo
3
bedrooms
2
Full
8
guests
4.9
(98 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: • Family friendly with tons of onsite amenities • One of very few handicapped accessible units • Living room and main bedroom accessible to the private balcony • Loc
Sunset Vistas 207S
Condo
2
bedrooms
1
Full, 1 Half
6
guests
4.9
(24 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 504 - Premier
Condo
2
bedrooms
2
Full
6
guests
4.9
(55 Reviews)
***PLEASE NOTE: THE ELEVATOR WILL BE OUT OF SERVICE FOR A SHORT TIME FROM MAY 1ST, 2026 FOR APPROX 1 WEEK. SOME DAYS IN THAT WEEK MAY NOT BE AFFECTED AT ALL OR VERY LITTLE, SOME DAYS MAY HAVE NO ELEVATOR SERVICE FOR A FULL DAY. REPAIRS/UPDATES BEING DONE. DATES COULD VARY BASED ON WEATHER. PLEASE CALL FOR DETAILS **** Stay more, SAVE more! We o
Oceana 204 East
Condo
2
bedrooms
2
Full
6
guests
4.9
(53 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 : • Short proximity to the onsite heated pool. • All the fabulous amenities including two Hot Tubs, Charcoal BBQ Grills, Community Gazebos, Shuffleboard, Volleybal
Land's End 9-304 Beach Front - Premier
Condo
2
bedrooms
2
Full
4
guests
4.9
(48 Reviews)
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