Madeira Beach


Properties Available 79 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: • 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 (119 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: * Beachfront Property with Direct Access to the Beach* New and Beautiful Updates!* Watch Stunning Sunsets from your Private Balcony* Onsite Heat Pool and Hot Tub
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.



Arie Dam 202
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (96 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)
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 (6 Reviews)
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 visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. If you can vacation for a minimum of 1-month, this beautiful condo is t
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.



Villa Madeira 208
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 5 guests
Rating 5 (8 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 1B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (74 Reviews)
Top Reasons To Book This Madeira Beach Condo:* Beachfront, End Unit Condo on 5th Floor with Amazing Gulf and Beach Views* Direct Beach Access, Heated Pool, Hot Tub, Shuffleboard, Tiki Bar, and Large Pool Deck all On Grounds* Great Location - Walk to John’s Pass Village and Boardwalk, Restaurants, Shops, or Hop on the Trolley!* Private Balcony off L
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 1-501
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (5 Reviews)
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 visit. • Located minutes from Florida's main attractions, just North of John's Pass Village. Stay more, SAVE more! We offer lower nightly rates on extended stays from
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 404 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (69 Reviews)
Top Reasons To Book John's Pass-Time #2:* Beachfront Property with Direct Beach Access* Gulf Views from your Private Balcony* Shared Beachfront Area with Picnic Table, Hammock and Charcoal Grill* Great Location - Walk To John's Pass Village and Boardwalk* Professionally Managed, 24/7Welcome to John's Pass-Time Beach Cottage #2, a peaceful 2-be
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 #2
House
Bedrooms 2 bedrooms
Bathrooms 1 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: • Spacious screened balcony featuring breathtaking views of the Gulf of Mexico. • Shared covered lounge chairs and access to the heated swimming pool during your vi
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 206
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (61 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)
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:* Location, Location, Location: Next to John's Pass and directly across from the sugar sand beach, with safe access via the pedestrian crosswalk light.*
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 Bay Resort I 1505
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (109 Reviews)

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