Shores of Madeira
425 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 Home:* Single Family Home all to Yourself* 2 Blocks from the Beach!* Awesome Wrap Around Deck* Dogs Welcome (2 max. Fees Apply)* Private Yard Fully Fence
Bates Avenue House
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 : • 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 10-205 Beach Front
Condo
2
bedrooms
2
Full
4
guests
4.9
(29 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: * 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
2
bedrooms
2
Full
6
guests
4.9
(95 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:* 173 Yards to the Gulfport Beach Recreation Area* 5 Miles to St. Pete Beach* Pet Friendly up to 20lbs. (Additional Cost Applies) * On-Site Parking and Laundry Faci
Beach Quarters #4
Condo
1
bedrooms
1
Full
4
guests
4.9
(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: • 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
(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. About this Land's End Condo:This top floor 2 bedroom, 2 bathroom has been nicely updated and is ready for you! The kitchen has been beautifully updated and is fully equipped and ready
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.
Land's End 3-404 Bay Front
Condo
2
bedrooms
2
Full
4
guests
4.9
(23 Reviews)
Top Reasons To Book This Beachfront Condo:* Amazing Gulf and Beach Views from the 7th Floor - Stunning Sunsets!* Heated Pool, Hot Tub, Gas Grills, Direct Beach Access On Grounds* Spacious and Comfortable 2 Bedroom, 2 Bathroom Condo with Private Balcony* Close to John's Pass Village and Boardwalk - Less than 1 Mile Away* Professionally Managed,
Sea Breeze 704
Condo
2
bedrooms
2
Full
6
guests
5
(4 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
(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 this Condo:* Beachfront Property with Direct Beach Access Onsite* Awesome Onsite Amenities - Large Heated Pool, Hot Tub, Fitness Center, Snack Bar, Kiddie Pool and Mo
Sunset Vistas 302S
Condo
2
bedrooms
2
Full
6
guests
4.6
(37 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 6-301 Beach Front
Condo
2
bedrooms
2
Full
4
guests
5
(53 Reviews)
Top Reasons To Book This Beachfront Condo:* Direct Beachfront Condo with Stunning, Unobstructed Views from the 6th Floor* Spacious Pool Deck with Lounge Chairs, Heated Pool, and Hot Tub* Other Onsite Amenities Including Direct Beach Access, Gas Grills, Shuffleboard, and Elevator* Stylish, Fully Updated Condo with Modern Finishes* Professionall
Ocean Sands 2-602
Condo
2
bedrooms
2
Full
6
guests
5
(1 Reviews)
Top Reasons To Book This Single Family Home:* Main House Plus Attached In-Law Suite for Added Privacy* About a 5-minute Walk to the Beach with Nearby Public Beach Access* Covered Lanai, Outdoor Deck, Fenced in Yard Space - Dog Welcome!* Outdoor Shower, Gas Grill, Gas Firepit - Great Outside Area to Hangout* Professionally Managed, 24/7Welcome
Sunsets and Sand Beach Getaway
House
4
bedrooms
2
Full, 1 Half
9
guests
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