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: * Beach access directly across the street as well as on site fishing and charter boats. * Gym Available (Building II) * Short stroll away from many shops and resta
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Bay Resort I 1502
Madeira Bay Resort I 1502
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (52 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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Surfside South #312
Surfside South #312
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
 New Property!
Top Reasons to Book this NEW Townhome: * Just Built and Everything is New! - 2025* Easy Walk to Madeira Beach, Approx. 300ft* Private Rooftop Deck with Seating - Great Hangout Spot!* Spacious, Elegant, Classy Townhome* Onsite Heated Community Pool* Professionally ManagedStay 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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Azul Townhomes A3 - Sunrise
Azul Townhomes A3 - Sunrise
Townhouse
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 12 guests
Rating 5 (19 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.



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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #2
John's Pass-Time Beach Cottage #2
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 5 (12 Reviews)
**Please note that due to damage from the recent hurricanes the elevators may be in and out of service. **Top Reasons To Book Ocean Sands I-808: * Beautiful Beachfront Condo on 8th Floor* Direct Beach Access on Grounds * Large Deck with Heated Pool, Lounge Chairs and Hot Tub* Private Balcony with Seating* Professional ManagedWelcome to Ocean
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Ocean Sands 1-808
Ocean Sands 1-808
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 4 guests
Rating 5 (15 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.



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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Norte 416
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: * Beachfront Condo with direct views of the Gulf of Mexico* Heated Pool and Hot Tub on Grounds* Private Balcony Facing the Beach* Spacious and Upda
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Sea Breeze 503
Sea Breeze 503
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (18 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 Beautiful Townhome:* Brand New Townhouse with Modern Design and Amenities* 4 Floors Featuring a Rooftop Deck with Amazing Views* 5 Spacious Bedrooms and 4 F
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Azul Townhomes A5
Azul Townhomes A5
Townhouse Pet Friendly
Bedrooms 5 bedrooms
Bathrooms 4 Full
Guests 11 guests
Rating 5 (17 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 saltwater swimming pool du
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Villa Madeira 506 - Premier
Villa Madeira 506 - Premier
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (44 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: • Private and beautifully furnished balcony overlooking the Gulf of Mexico! • Unit includes free Wi-Fi and free parking! • Beautifully decorated throughout to refl
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.



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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Arena De Madeira 502- Premier
Arena De Madeira 502- Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (21 Reviews)
The Harbor At Town Center is a brand new property in Madeira Beach!Top reasons to Book: • Private and beautifully furnished balcony overlooking the marina! • Just a block from beautiful, white sand Madeira Beach! • Wonderful amenities such as a pool and spa as well as free Wi-Fi, secured parking, and an in-unit washer and dryer! • Beautifully decor
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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

The Harbor Condo 503 - Premier
The Harbor Condo 503 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full, 1 Half
Guests 7 guests
Rating 5 (8 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.



🌴 Save Up to 10% on Your Florida Getaway 🌴



Save up to 10% on qualifying stays of 4 nights or more at Resort Rentals when you book by September 25, 2026. Travel August 22–December 31, 2026, and use code ENDOFYEAR10 at checkout.


Plan the beach getaway, family vacation, or end-of-year retreat you’ve been waiting for.


*Offer is valid on new online bookings when you book by September 25, 2026, for 4-night minimum stays from August 22 through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Del Mar 302
Madeira Del Mar 302
Condo
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 5 (9 Reviews)

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