Cottages at Madeira Beach


Properties Available 398 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
NEW YEAR 2026

Get 10% OFF select  properties when you stay 7-14 nights between 1/2/26-4/3/26! Book by January 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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 7-401 Beach Front - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (44 Reviews)
Top Reasons To Book This Beautiful Home:* Beautifully Updated Top to Bottom - Incredibly Lovely Home!* Easy Walk to the Beach - Only 450 Feet! * Single Family Home - Privacy and Comfort is All Yours!* Covered Outdoor Area with Large Sectional, Gas Grill and Outdoor Shower* Fantastic Neighborhood, Walkable and Peaceful* Professionally Manage
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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.  

Curvy Coco
House
Bedrooms 3 bedrooms
Bathrooms 2 Full, 1 Half
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:* 173 Yards to the Gulfport Beach Recreation Area* 5 Miles to St. Pete Beach* Pet Friendly up to 20lbs. (Additional Cost Applies) * On-Site Parking and Laundry Faci
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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.  

Beach Quarters #5
Condo Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (52 Reviews)
Top Reasons To Book Bungalows #4:* 400ft away from Beach Access - Just Across the Street* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Large 2 Bedroom, Poolside Unit* Onsite Heated Pool, Outside Games and Charcoal Grills* Professionally Managed, 24/7Welcome to The Bungalows #4! This updated 2-bedroom, 1-bathroom unit is the perfect spot for your
The Bungalows #4
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 6 guests
 New Property!
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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 1-303 Gulf View
Condo
Bedrooms 1 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (60 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 Awesome Townhouse: * Short and convenient 3-minute walk to the sand* Spacious Layout, luxurious furnishings, plenty of room for the entire family!* Additional o
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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.  

Redington Townhouse 16303 - Pelican Paradise
Redington Beach Area
Bedrooms 4 bedrooms
Bathrooms 3 Full
Guests 10 guests
Rating 5 (59 Reviews)
Top Reasons To Book Bungalows #3:* Large 2 Bedroom, Poolside Unit* Charming Property Across the Street from Beach Access - Only 400 ft away!* Dogs Allowed - 1 Dog, 50lb Max. Fees Apply* Onsite Heated Pool, Outside Games and Charcoal Grills* Small, Quaint Property - Only 10 Units Total* Professionally ManagedWelcome to The Bungalows #3! This
The Bungalows #3
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 6 guests
 New Property!
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 Beachfront Condo:* Beachfront Condo, Corner Unit on 6th Floor * All the Amenities- Beachside Heated Pool, Hot Tub, Shared BBQ Area and a Large Pool Deck- All O
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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.  

Sand Castle II #2601 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 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
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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 1-405 Gulf View - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (25 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 #10:* 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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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 #10 - Seascape
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (12 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: • Ground floor for easy access to the onsite pool and BBQ area! • Low density area located in Redington Shores. • Located just 4.5 miles South is the well known Jo
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 31, 2026.


Use code: "NEWYEAR2026" at checkout.


Offer is valid on new online bookings only when you book by January 31, 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.  

The Shores 103
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (62 Reviews)
Top reasons to book this Townhouse: • Direct Beach Access Path • Just a short stroll to relax on the beautiful white sands of Treasure Island! • Low density complex, still close to all the action and entertainment! • EV-Electric Vehicle Charger available for our guests! The Sand Dunes Townhome has many interior upgrades with every possible amen
Sand Dunes Townhome C2
House
Bedrooms 2 bedrooms
Bathrooms 2 Full, 1 Half
Guests 8 guests
Rating 5 (14 Reviews)

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

I agree