Cottages at Madeira Beach


Properties Available 395 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 Land's End Condo:* Amazing Views of the Gulf of Mexico and Blind Pass Waterway* End Unit for Added Privacy* Gated Community with Secure Access* Lots of Onsi
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 5-305 Gulf-Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (5 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
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Amadeus 9
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (44 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
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sea Club #15 - Sand Dollar
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (6 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. ****NOTICE: SUNSET VISTAS WILL BE DOING A WALKWAY RESURFACING PROJECT THROUGH EACH BUILDING AND ON EACH FLOOR NOVEMBER 2025 - ESTIMATED END OF JANUARY 2026. SOME NOISE AND FLOOR CLOSURES
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sunset Vistas 411N
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (66 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
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Land's End 5-303 Gulf-Bay Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (36 Reviews)
Top Reasons to book : •Totally Remodeled in 2024! • 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, this community offers the best of both worlds- easy access to the Bay and Bea
Land's End 7-406 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (50 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 #39:* Close to Beach Access!* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway*
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Sea Club #39 - Seaside Serenity
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (22 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: Please note that restoration work is underway. Parking is limited onsite. Noise may be experienced while work is ongoing. Beach Access and Pool are OPEN! ***
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Villa Madeira 405 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (18 Reviews)
**Please note that due to damage from Hurricane Helene, this property temporarily has no access to the elevators. At this time, we do not have a guaranteed date for this to be accessible, but we do not anticipate any interference with 2025 stay dates. Please reach out with any questions. Rates lowered!**Top Reasons to Book View West #1:* Beachfron
View West #1
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (3 Reviews)
Top Reasons To Book Sunset Vistas #405S:* Beachfront Property with Direct Onsite Beach Access* Large Heated Pool with a Jacuzzi for Ultimate Relaxation* Splash Pool for Kids - Fun for the Whole Family* Spacious Condo with Private Balcony* Café and Beach Bar Onsite - Perfect for Dining and Drinks with a View* Professionally Managed, 24/7 Servi
Specials Tag Special
New Property Introductory Discount

New Property Introductory Discount 

Limited time only Promo Code NEW100

Sunset Vistas 405S
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (1 Reviews)
Top Reasons to Book this Beautiful Home:* Single Family Home on the Intracoastal Waterway* Large, Private Deck with Saltwater Pool* Fishing Dock* Dogs Allowed - (1 dog max, 50lbs and under. Extra Fee Applies)* Professionally ManagedStay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No coupon code needed! Just
Parrots Cove
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (1 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 Beautiful Condo:* 2 Private Balconies with Bay and Marina Views* Easy Beach Access Just Across the Street, Approx. 300 ft* Onsite Heated Pool and Hot Tub*
Specials Tag Special
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 17, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 17, 2026 for 7-14 night stays from January 2, 2026 - April 3, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.  

Madeira Bay Resort II - 606
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (6 Reviews)

Tell us what you're looking for and someone will contact you with available options.

I agree