Madeira Beach


Properties Available 80 properties available
*** POOL UPDATE: The pool is temporarily closed while necessary repairs are being completed. A reopening date has not yet been confirmed, but we hope it will happen soon. We will remove this note from the listing when all is back open. Thank you for your understanding. ***Top Reasons To Book This Condo:* Direct Beach Access and Heated Beachfront P
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Norte 505
Condo
Bedrooms 2 bedrooms
Bathrooms 1 Full, 1 Half
Guests 6 guests
 New Property!
**NOTICE: Guests may experience some extended wait times for the elevator. One of the two elevators is currently operational and that they are actively working on getting the second elevator back in service. Thank you for your patience during this period. **Stay more, SAVE more! We offer lower nightly rates on extended stays from Sept-Mar. No cou
Madeira Vista 201
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.7 (15 Reviews)
Top reasons to Book: • Newly renovated Kitchen with brand new appliances! • All the Amenities- Beachfront heated pool, hot tub, shared BBQ Area, Free wifi and onsite laundry facilities. • Located just one mile South is the well known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment! This gorgeous South W
Sea Breeze 401
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (80 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.




🌴 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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. 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 (71 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 panoramic beachfront views from your large private balcony. • Onsite outdoor amenities in paradise include a beautiful, heated pool, tiki huts, BBQ Grills
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Las Brisas 202
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 4.9 (113 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
Villa Madeira 204 - Premier
Condo
Bedrooms 3 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (15 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: * 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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Bay Resort I 1502
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 4.9 (54 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
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #1
House
Bedrooms 2 bedrooms
Bathrooms 1 Full
Guests 4 guests
Rating 4.8 (6 Reviews)
Top Reasons To Book This Condo:* Beach Access Directly Across the Street – Easy access via a designated guest crosswalk, just steps from the property.* Walk to John’s Pass – Just a 2–3 minute walk to restaurants, shopping, entertainment, water activities, and more.* Resort-Style Amenities – Heated pool, hot tub, spacious pool deck, lounge chairs
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Bay Resort II - 314
Condo
Bedrooms 2 bedrooms
Bathrooms 2 Full
Guests 6 guests
Rating 5 (11 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 Beachfront Condo:* Beachfront Condo Directly on Madeira Beach* Community Heated Beachside Pool with Lounge Chairs* Minutes from John’s Pass Village and Boardwal
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. 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 (75 Reviews)
Top reasons to book: • Don’t forget your fur baby! This unit is dog friendly (restrictions and fees apply). • Onsite outdoor resort style pool (heated seasonally) with new pool deck furniture. • Located just 1.5 miles South is the well known John’s Pass Village which is loaded with tons of shopping, restaurants, and entertainment! Stay more, SAVE m
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

Madeira Del Mar 305
Condo Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 Full
Guests 8 guests
Rating 4.9 (92 Reviews)
Top Reasons To Book John's Pass-Time Beach Cottages:* Beachfront Property with Direct Beach Access* Full Property to Yourself - Both Cottages - Great for Larger Families or Friends Traveling Together* Great Private Backyard Beach with Hammock, Grill and Picnic Table* 2 Private Entrances, 2 Great Deck/Patio Spaces* Gulf Views From the Upper Lev
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 October 31, 2026. Travel now–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 October 31, 2026, for 4-night minimum stays from now through December 31, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

John's Pass-Time Beach Cottage #1 and #2
House
Bedrooms 4 bedrooms
Bathrooms 2 Full
Guests 8 guests
Rating 5 (6 Reviews)

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