Shores of Madeira
423 properties available
Top Reasons To Book This Villa:* Short Easy Walk (about 500 ft) to Beach Access* Beautiful Intracoastal Waterway Views from your 2 Private Balconies* Waterfront Pool Deck with Lounge Chairs and Seating* Spacious 3-story Villa with 2 Bedrooms, Each with Attached Bathrooms* Professionally Managed, 24/7Welcome to Bayview Villas #101, a beautiful
Bayview Villas 101
Villa
2
bedrooms
2
Full, 1 Half
6
guests
5
(2 Reviews)
NOTICE **Please note that due to damage from the recent hurricanes, this property temporarily has no access to onsite amenities. Parking is currently limited onsite. There may be some noise while restoration work is finishing up. **Top Reasons To Book This Condo:* Beachfront Location with Direct Beach Access* Stunning Gulf and Beach Views From t
Madeira Vista 406
Condo
2
bedrooms
2
Full
5
guests
New Property!
****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)
****NOTICE: The building is currently undergoing a major exterior renovation project beginning December 1, 2025 and is expected to continue for approximately 10-12 months, length could vary. Construction activity typically takes place Monday–Friday from 8:00 AM to 4:30 PM, and guests may experience noise during these hours. Please note: Access to
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.
Bayshore Yacht & Tennis 205
Condo
2
bedrooms
2
Full
6
guests
5
(2 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
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
2
bedrooms
1
Full
4
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 this Beach Front Condo: * Short Walk to the On-site Heated Pool* Spacious Balcony with Beach Views* Fabulous Amenities including two Hot Tubs, Charcoal BBQ Grills, Co
Land's End 10-303 Beach Front - Premier
Condo
2
bedrooms
2
Full
4
guests
5
(5 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
5
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 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)
Top reasons to book this Townhouse: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all the action and entertainment! • EV-Electric Vehicle Charger available for our guests! The Sand Dunes Townhome has many interior upgrades with every possible amen
Sand Dunes Townhome C2
House
2
bedrooms
2
Full, 1 Half
8
guests
5
(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 this Townhome: - Directly on the Beach- Dog Friendly (Additional Costs Apply) - Two Balconies- Wine Fridge, Large TVs throughout- Close to Restaurants- Professional
Beach Haven #C7
Townhouse
3
bedrooms
2
Full, 1 Half
7
guests
4.9
(77 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:-Less than 400 Feet to the Beach-Dog Friendly (Restrictions and additional fees apply)-Private off-street parking-Recently Updated and New Stainless Steel Appliance
Beach Life 3
House
3
bedrooms
2
Full
6
guests
4.9
(47 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
Emerald Isle 104
Condo
2
bedrooms
2
Full
4
guests
4.8
(62 Reviews)
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