Cottages at Madeira Beach
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 Sea Club #402:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway*
Sea Club #402 - Isle Be Back
Condo
1
bedrooms
1
Full
5
guests
5
(9 Reviews)
*** CONSTRUCTION NOTICE: SAND CASTLE I WILL BE UNDERGOING BUILDING RENOVATION WORK BEGINNING AUG. 2026 LASTING FOR APPROX. 4 MONTHS, TIME COULD VARY. WORK WILL BRING NOISE, POSSIBLE INTERMITTENT POOL CLOSURES, ONSITE PARKING MAY VARY. WORK TO INCLUDE PAINTING, GARAGE REPAIRS, WINDOW REPLACEMENTS, LOBBY UPDATE, WALKWAY WORK, CONCRETE REPAIR. ***Stay
Sand Castle I #804
Condo
3
bedrooms
2
Full
6
guests
4.9
(40 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 9-404 Beach Front - Premier
Condo
2
bedrooms
2
Full
4
guests
4.9
(65 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: * Walking distance to Sunset Beach, one of the BEST beaches on Treasure Island!* Fresh New Updates - 2025 * Private Patio with Outside Seating and Gas Gri
Good Vibrations - Beach House
House
2
bedrooms
2
Full
4
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. This stunning Bay front condo has been completely renovated including new windows, sliding doors and new flooring. Fully equipped new kitchen with custom cabinets, granite counter top
Land's End 4-303 Bay Front - Premier
Condo
2
bedrooms
2
Full
6
guests
4.6
(22 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
Bayshore Yacht & Tennis 806
Condo
3
bedrooms
2
Full
7
guests
5
(13 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)
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 Chic Condo:* Beach Access Located Across the Street* Newly Renovated Unit* All the Amenities: Well Maintained, Seasonally Heated Pool + Large Sundeck* BBQ and
Barefoot Beach Resort A202
Condo
1
bedrooms
1
Full
5
guests
4.9
(70 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
(21 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)
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 1-307 Gulf View
Condo
2
bedrooms
2
Full
6
guests
5
(39 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 #15:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* P
Sea Club #15 - Sand Dollar
Condo
1
bedrooms
1
Full
2
guests
5
(6 Reviews)
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