Cottages at Madeira Beach


Properties Available 440 properties available
Top Reasons to Book this Land's End Condo: * Private Balconies Facing Channel - Watch the Boats and Dolphins Coming and Going* Alexa-Enabled Throughout Entire Condo* Close Proximity to the Large, Heated Pool* Tons of Onsite Amenities - Heated Pool, Hot Tub, Tennis and Pickleball, Shuffleboard, Sand Volleyball Court, Gated Community, BBQ Grills*
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 1-206 Bay Front-Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (8 Reviews)
Top Reasons To Book This Beachfront Condo:* Direct Beachfront Condo with Stunning Gulf Views* Heated Community Pool and Direct Beach Access Onsite* Private Balcony with Table and Chairs Overlooking the Beach* Great Location with Easy Trolley Access and Nearby Restaurants and Local Favorites* Professional Managed; 24/7Welcome to Gulf Shores #20
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.



Gulf Shores #205
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
 New Property!
Top Reasons To Book Bungalows #9:* Onsite Heated Pool and Large Pool Deck with Chairs and Umbrellas* Great Common Space with Charcoal Grills, Tables and Chairs and Family Fun Outdoor Game Area* Charming Property Across the Street from Beach Access - Only 400 ft away!* Spacious and Bright Studio* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Pr
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.



The Bungalows #9
Studio Pet Friendly
Bathrooms 1 Full
Guests 2 guests
Rating 4.8 (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. Top reasons to Book: • Beach access is a short distance from the property, just across the street for your convenience. • Property includes an on-site pool (heated seasonally) • Also o
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 Shell 24
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.9 (27 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: • All the Amenities! Large Heated Pool, Kiddie Pool, Hot Tub, Fitness Center, Bicycles, Beach Tiki Bar and Café all in one location!• Living room and main bedroom
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 501W
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (56 Reviews)
Top reasons to Book: • 3 private balconies with scenic views! • Beachside pool onsite (Heated Seasonally) • Beautifully decorated throughout to reflect coastal comfort. This bright and spacious 2 bedroom, 2 bath condo on Indian Rocks Beach that has everything you need and more so your vacation search stops here!!!! Open floor plan, hard wood floors
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.



Seahorse 401
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 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: • 4 total units for this building, the perfect getaway for the entire family! • TWO balconies per condo, one facing West overlooking the Gulf and one facing East.
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.



Sunset Villas 1
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (83 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
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (28 Reviews)
Top Reasons To Book This Condo:* Right Across the Street From the Beach - Easy Access, 300ft!* Great Onsite Amenities: Heated Pool, Hot Tub, Pool Deck with Lounge Chairs, Workout Room* Modern, Updated Condo with Private Balcony* Great Location - Walk to John's Pass Village and Boardwalk* Professionally Managed, 24/7Welcome to Madeira Bay II #3
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.



Madeira Bay Resort II - 314
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (7 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:* 180 ft from Public Beach Access* Private Entrance with 2 Parking Spaces Any extra-large vehicles may have to park in city overflow due to restricted sp
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 Livin 3 - 3 Bedroom Upstairs
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full, 1 Half
Guests 6 guests
Rating 4.7 (21 Reviews)
Top Reasons to Book this Beautiful Home:* Single Family Home on the Intracoastal Waterway* Large, Private Deck with Saltwater Pool (Not Heated)* 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
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.



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: • All the Amenities-Beachfront heated pool onsite shuffleboard and shared BBQ grills! • Take in unforgettable beachfront views and warm sunshine from your private
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.



Caprice 501
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.8 (102 Reviews)

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