Madeira Beach


Properties Available 79 properties available
**Please note that due to damage from the recent hurricanes the elevators may be in and out of service. **Top Reasons to Book this Beachfront Condo:* Beachfront Condo with Direct Views of the Gulf of Mexico* Open and Spacious Condo on 10th Floor* Large Pool Deck with Table and Chairs* Heated Pool, Hot Tub and Shuffleboard on Grounds * Central Locat
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 1-1002
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (13 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. **NOTICE: Please note that due to damage from the recent hurricanes, this property temporarily has no access to onsite amenities. Parking is limited onsite. 1 elevator is currently ope
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 Vista 601
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (20 Reviews)
Top Reasons To Book This Beautiful Condo:* Quick and Easy Walk to the Beach - 5 Minutes, Only .2 Miles!* Onsite Heated Pool* Spacious, Beautifully Updated 3 Bedroom/3 Bathroom Condo* Great Location - Walkable to Beach, Grocery Store, Mini Golf and Restaurants* Professionally Managed, 24/7Welcome to Madeira Del Mar 302! This spacious 3-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.



Madeira Del Mar 302
Condo
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (6 Reviews)
Top Reasons to Book this AMAZING Townhome: * Brand New Build in 2025* Easy Walk to Madeira Beach, Approx. 300ft* Private Roof Top Deck with Views and Seating - Great Hangout Spot!* Spacious and Comfortable, Great for Families or Larger Groups* Onsite Heated Pool* Professionally Managed Welcome to Azul Townhome B3, a brand-new, four-story town
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.



Azul Townhomes B3
Townhouse
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 11 guests
Rating 5 (23 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 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)
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: • 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. •Newly updated throughout in December 2023!Stay more, SAVE more! We offer
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 408 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 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: • 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 2B - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (87 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)
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 4A - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (99 Reviews)
Top Reasons to Book:* Stunning Views from Private Balcony * Heated Beachfront Pool* Hot Tub * Beach Front* In-unit washer and dryer* Professionally Managed For a serene and rejuvenating vacation experience with unparalleled Gulf views and top-notch amenities, Surfside South 312 is the ideal choice. This two-bedroom, two-bathroom condo offers a perf
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.



Surfside South #312
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
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