Cottages at Madeira Beach
424 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 Sea Club #29:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Sea Club #29 - Our Sunrise Nest
Condo
2
bedrooms
2
Full
6
guests
5
(10 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:• Unobstructed view of the gulf from the private balcony• Beach access directly across the street (with crossing light for safety!) About 200 steps to the sand!• Gy
Madeira Bay Resort I 1504
Condo
2
bedrooms
2
Full
6
guests
4.9
(56 Reviews)
****NOTICE OF ROOF WORK - BUILDING 7. ROOF WORK WILL BEGIN JUNE 1ST 2026 FOR APPROX 6 WEEKS. *** 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 fabul
Land's End 7-402 Beach Front - Premier
Condo
2
bedrooms
2
Full
6
guests
4.9
(48 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: •Walking distance to a wide variety of local restaurants and entertainment. •Located just a block from the easy beach access. •Includes access to a shared dock on
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.
Amadeus 2
Condo
1
bedrooms
2
Full
3
guests
4.9
(52 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 Sea Club #10:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
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.
Sea Club #10 - Seascape
Condo
2
bedrooms
2
Full
4
guests
5
(13 Reviews)
****NOTICE OF ROOF WORK - BUILDING 6. ROOF WORK WILL BEGIN MARCH 30TH 2026 FOR APPROX 6 WEEKS. *** 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 fab
Land's End 6-205 Beach Front - Premier
Condo
2
bedrooms
2
Full
6
guests
5
(62 Reviews)
****NOTICE OF ROOF WORK - BUILDING 4. ROOF WORK WILL BEGIN MID JULY 2026 FOR APPROX 6 WEEKS. DATES MAY VARY. *** 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 Land's End 4-206:* Incredible Bay Views from Pr
Land's End 4-206 Bay Front - Premier
Condo
2
bedrooms
2
Full
6
guests
5
(12 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 Home:* Single Family Home with Heated Pool all to Yourself* Spacious and Beautifully Updated* Desk Space Available for Working Vacation* Large Outside Deck
Beach Bound
House
3
bedrooms
2
Full
8
guests
5
(26 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 2B - Premier
Condo
2
bedrooms
2
Full
6
guests
5
(87 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: • Don’t forget your fur baby! This unit is dog friendly (restrictions and fees apply). • Onsite outdoor resort style pool (heated seasonally) with new pool deck fu
Madeira Del Mar 305
Condo
3
bedrooms
3
Full
8
guests
4.9
(85 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: • Take in unforgettable panoramic beachfront views and warm sunshine from your private balcony. • Short drive to St Petersburg- loaded with great museums, shops and r
Emerald Isle 502 - Premier
Condo
3
bedrooms
2
Full
6
guests
4.9
(48 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, Volleyball,
Land's End 10-202 Beach Front - Premier
Condo
2
bedrooms
2
Full
4
guests
5
(42 Reviews)
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