Cottages at Madeira Beach

Properties Available 427 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 #102:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway*
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Sea Club #102 - Another Day in Paradise
Sea Club #102 - Another Day in Paradise
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 5 (19 Reviews)
Top Reasons to Book this Land's End Condo: * Beachfront Condo with Beautiful Updates Throughout* Private Balcony with Stunning Views* Gated Community* Amenities: Beach Access, Heated Pool, Hot Tub, Tennis and Pickleball, Shuffleboard, Sand Volleyball* Professionally ManagedStay more, SAVE more! We offer lower nightly rates on extended stays f
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Land's End 11-302 Beach Front - Premier
Land's End 11-302 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (13 Reviews)
Top Reasons to Book Gulfside Retreat: * Gorgeous 3-Story Single Family Home with Private Elevator* Easy Walk to the Beach - About 350 Yards* 2 Spacious, Private Balconies with Seating* Quiet Neighborhood Location* Bright, Beautiful and Modern Home* Professionally ManagedWelcome to Gulfside Retreat! This stunning 3-story single-family home bo
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Gulfside Retreat
Gulfside Retreat
House
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 9 guests
Rating 5 (25 Reviews)
*** NOTICE: At Harbor House there is still active work on grounds. Buildings have gates in place and there will be construction taking place, noise will be associated with this. Parking will vary. Onsite Laundry Room currently closed. ***Top Reasons To Book:* Beautiful Beaches Right Across the Street* Access to Beach Front Pool and Grills Acros
Harbor House 37
Harbor House 37
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (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. Top Reasons to Book Sea Club #49, "Beach Oasis":* Close to Beach Access, About 400ft!* Private, Screened in Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Sea Club #49 - Beach Oasis
Sea Club #49 - Beach Oasis
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (13 Reviews)
Top Reasons To Book This Condo:* Beach Access Across the Street - Approx. 2-minute walk (about 475 ft)* Heated Pool with Spacious Sun Deck and Lounge Chairs* Dedicated Workspace for Remote Work Convenience* Back Patio Area with Table and Chairs - Great Outdoor Dining Spot!* Bonus Sleeping Area with Extra Full Bed—Great for Families or Groups*
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Barefoot Beach Resort F106
Barefoot Beach Resort F106
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (29 Reviews)
****NOTICE OF ROOF WORK - BUILDING 4. ROOF WORK WILL BEGIN MID JULY 2026 FOR APPROX 6 WEEKS. DATES MAY VARY. *** SPECIAL OFFER*: Stay Longer, Save BIG! Apply promo code at checkout to enjoy exclusive discounts:• Promo code DD10: Stay 21–34 nights and save 10% on rent.• Promo code DD15: Stay 35 nights or more and save 15% on rent.*Terms: Discoun
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Land's End 4-401 Bay Front - Premier
Land's End 4-401 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (57 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 Bay Front Condo: * Short Walk to the On-site Heated Pool* Spacious Balcony with Great Water Views* Gorgeous Interior and Decor* Fabulous Amenities including tw
Specials Tag 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 1-208 Bay Front - Premier
Land's End 1-208 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (27 Reviews)
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, this community offers the best of both worlds- easy access to the Bay and Beach.Stay more, SAVE more! We
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Land's End 6-203 Beach Front
Land's End 6-203 Beach Front
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 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:-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
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Beach Life 3
Beach Life 3
House Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (53 Reviews)
Top Reasons To Book This Sunset Vistas Condo:* Beach Access Onsite—The Sand is Just Steps Away* Great Amenities - Large Heated Pool, 2 Hot Tubs, Kiddie Pool with Fountains, Workout Room, Charcoal Grills* Partial Gulf Views from Private Balcony - 3rd Floor* Spacious 2-bedroom, 2-bath Condo That Sleeps up to 6 Guests* Professionally Managed, 24/
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Sunset Vistas 302N
Sunset Vistas 302N
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 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 Sea Oats #101:* Beautiful Beachfront Location* Steps to the Beach* Private Balcony Overlooking the Gulf of Mexico* Large Beachfront Heated Pool* Professionally Mana
Specials Tag Special
Stay Longer on the Beach & Save 5%

Book your long-term Florida beach getaway now and take advantage of 5% savings on stays of 28+ nights. Use STAYLONGER5 on travel between October 1, 2026 and January 31, 2027 at select condos and homes.


*Offer is valid on new online bookings when you book by January 1, 2027, for stays of 28 nights or more with travel between October 1, 2026 and January 31, 2027. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.



Sea Oats 101
Sea Oats 101
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (10 Reviews)

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