Madeira Beach


Properties Available 79 properties available
Top Reasons To Book This Beachfront Condo:* Direct Beachfront Condo with Stunning, Unobstructed Views from the 6th Floor* Spacious Pool Deck with Lounge Chairs, Heated Pool, and Hot Tub* Other Onsite Amenities Including Direct Beach Access, Gas Grills, Shuffleboard, and Elevator* Stylish, Fully Updated Condo with Modern Finishes* Professionall
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.



Ocean Sands 2-602
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (2 Reviews)
Top Reasons to Book This Home: * Quick and Easy Walk to Beach Access - Only 200ft Away!* Single Family Home to Yourself* Backyard Area with Gas Grill and Outdoor Dining Table* Spacious Open-Concept Living* Professionally ManagedWelcome to Sunset Paradise Home, your perfect beach getaway in Madeira Beach! Enjoy the entire single-family home to your
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 Paradise
House
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
Rating 5 (2 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 Madeira Del Mar 301:* Don’t forget your fur baby! This unit is dog friendly (restrictions and fees apply). * Onsite outdoor resort style pool (heated seasonally) wi
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.



Madeira Del Mar 301
Condo Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (38 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: • You’ll love the beautiful décor, and comfortable furnishings throughout this unit • As you enter, you'll be greeted by floor to ceiling sliding glass doors and
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.



Trillium 4C - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 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: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs; access to the heated saltwater swimming pool during yo
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.



Villa Madeira 609
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 4.8 (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: • Direct waterfront views from your private dock! • The location- Walking distance to the sugary white sands of Madeira Beach. • Plenty of comfortable outdoor furn
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.



Coconut Paradise
House
Bedrooms 3 bedrooms
Bathrooms 1 Full
Guests 8 guests
Rating 4.9 (57 Reviews)
Top Reasons To Book This Beachfront Condo:* Amazing Gulf and Beach Views from the 7th Floor - Stunning Sunsets!* Heated Pool, Hot Tub, Gas Grills, Direct Beach Access On Grounds* Spacious and Comfortable 2 Bedroom, 2 Bathroom Condo with Private Balcony* Close to John's Pass Village and Boardwalk - Less than 1 Mile Away* Professionally Managed,
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 Breeze 704
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (4 Reviews)
***POOL CLOSURE - THE POOL WILL BE CLOSED BEGINNING MAY 1ST, 2026 - MORE EXTENSIVE REPAIRS ARE REQUIRED AND CURRENTLY THERE IS NOT A SET REOPEN DATE - WE WILL REMOVE THIS NOTICE WHEN THE POOL HAS REOPENED. ******* New Photos Coming Soon ***Top Reasons To Book This Condo:* Beachfront Condo - Great Beach and Gulf Views from 4th Floor - Sunset Views
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 Norte 416
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
Rating 5 (6 Reviews)
Top Reasons To Book This Condo:* Quick and Easy Walk to the Beach - Approx. 175ft Away!* Shared Heated Pool for Year-Round Enjoyment* Spacious Pool Deck with Lounge Chairs for Relaxing and Soaking Up the Sun* Onsite fishing Dock Right on the Intracoastal Waterway* Awesome Waterway Views from your Private Balcony* Professionally Managed, 24/7W
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.



Skyline of Madeira 306
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (48 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: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico.• Shared covered lounge chairs and access to the heated swimming pool during your visi
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.



Villa Madeira 307 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (47 Reviews)
Top Reasons To Book John's Pass-Time #1:* Beachfront Property with Direct Beach Access* Ground Level Cottage, No Stairs Required* Large Private, Covered Deck with Table and Chairs* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #1, a charming and cozy
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.



John's Pass-Time Beach Cottage #1
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 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: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your vis
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.



Villa Madeira 202
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (120 Reviews)

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