Cottages at Madeira Beach


Properties Available 477 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 : • 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
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 3-206 Bay Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 4.9 (35 Reviews)
Top Reasons To Book This Suite:* Beach Views – Enjoy the Gulf Coast Right from Your Suite* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Separate Living Area with Sleeper Sofa – Room to Spread Out* Professionally ManagedWelcome to Tropic Terrace Suite #27, a fres
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.



Tropic Terrace Suite 27
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
 New Property!
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 : • 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
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 11-203 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (54 Reviews)
Top Reasons To Book Bungalows #7:* Onsite Heated Pool with Large Deck and Lounge Chairs* Across the Street from the Beach - Only 400 ft!* Fun Outdoor Space with Games, Seating, and Charcoal Grills* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Professionally Managed; 24/7 ServiceWelcome to The Bungalows #7! This updated 2-bedroom, 1-bathroom s
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.



The Bungalows #7
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 5 guests
Rating 5 (7 Reviews)
Top Reasons To Book This Suite:* Steps to the Beach – Onsite Path to Treasure Island's Sandy Shores* Ground Floor Suite - No Stairs Required* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Heated Pool – Perfect for Relaxing After a Day at the Beach* Separate Living Area with Sleeper Sofa – Room to Spread Out* Professionally
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.



Tropic Terrace Suite 21
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
 New Property!
Top Reasons To Book This Suite:* Heated Pool – Perfect for Relaxing After a Day at the Beach* Beachfront Access – Steps from Beautiful Treasure Island Beach* Great Location - 1 Mile to John's Pass Village and Boardwalk* Resort Amenities – Shuffleboard, Cornhole, Grills, and Recreation Room* Professionally ManagedWelcome to Tropic Terrace Suite
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.



Tropic Terrace Suite 12
Studio
Bathrooms 1 Full
Guests 2 guests
 New Property!
***NOTICE - POOL CLOSURE*** The pool will be closed for maintenance beginning Monday Sept 14, 2026 for approx. 2 weeks. Timeline may vary.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 Amazing Gulf Front
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.



Oceanside 302
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 4.8 (53 Reviews)
Top Reasons to Book Sea Club #10:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* Professionally ManagedStay 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 nig
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 #10 - Seascape
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (14 Reviews)
Top Reasons To Book This Beautiful Condo:* Beachfront, 5th Floor Location with Direct Gulf and Beach Views* Resort-Style Amenities - Heated Pool, Hot Tub, Sauna, Tennis/Pickleball Courts, Direct Beach Access* Amazing Beach to Walk with Unparallel Sand, Salt Air and Magnificent Gulf Views that Often Include Dolphins Swimming and Playing!* Spaci
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.



Reflections On The Gulf #502 - Paradise on the Gulf
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 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 Condo:* 180 ft from Public Beach Access* Private Entrance with 1 Parking Space Any extra-large vehicles may have to park in city overflow due to restricted spa
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 2 - 1 Bedroom Downstairs
Condo Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 3 guests
Rating 5 (25 Reviews)
Top Reasons to Book Sea Club #18:* Close to Beach Access* Private Balcony* Beautifully Landscaped Grounds* Onsite Heated Pool and Shuffleboard* Fishing Dock on Intracoastal Waterway* Professionally ManagedFloriday’s is a beautiful two-bedroom, two-bathroom condo located on the second story, featuring a covered balcony that overlooks lush community
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 #18 - Floridays
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (6 Reviews)

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