Madeira Beach Vacation Rentals and Condos for Rent

Get away from it all in this delightful 2 bedroom, 2 bath condominium in exclusive southern Madeira Beach. With a prime location across from John's Pass Village, and easy access to the one of a kind tropical Florida beaches. Beach Place #101 - Get away from it all in this delightful 2 bedroom, 2 bath condominium in exclusive southern Madeira Beach. With a prime location across from John's Pass Village, and easy access to the one of a kind tropical Florida beaches, here you will find comfortable living with every amenity. Free Wifi. There is one parking spot for Unit 101. You will be required t.......

4.7 Star Review

Enjoy oceanfront and pool views from this bright and well appointed 3 bedroom, 2 bath condominium on Madeira Beach Crimson on The Gulf #101 - Enjoy oceanfront and pool views from this bright and well appointed 3 bedroom, 2 bath condominium in sought after southern Madeira Beach. This vacation home has all the amenities, including location! location! location! as it sits directly across from popular John's Pass Village, and of course, beautiful clear blue beaches that Florida is well known for. Free WiFi. Crimson is a Smoke Free property including all private balconies and common areas. Please .......

4.4 Star Review

2 bedroom, 2 bathroom condo complete with balcony view of popular John's Pass in southern Madeira Beach. This ideally located condo includes heated beachside pool, BBQ grills and an on-site laundry. Beach Place #102 - Remodeled, 2 bedroom, 2 bathroom condo complete with balcony view of popular John's Pass in southern Madeira Beach. This ideally located condo includes heated beachside pool, BBQ grills and an on-site coin laundry for your convenience. Free Wifi. Beach Place unit #102 has one parking spot. You will be required to sign a rental agreement with prior to a reservation being confirmed.......

4.7 Star Review

Beautiful 3 bedroom, 3 bathroom condo complete with gulf views. This bright and airy 1,570 square foot property offers everything you need to create a memorable vacation Crimson on the Gulf #103 - It doesn't get much better than this when visiting southern Madeira Beach! Enjoy first class living in Crimson #103! Beautiful 3 bedroom, 3 bathroom condo complete with gulf views. This bright and airy 1,570 square foot property offers everything you need to create a memorable vacation. Designed with comfort in mind, guests will immediately notice the well thought out floor plan that includes a full .......

4.6 Star Review

You won't be disappointed with this wonderful beachfront 3 bedroom, 2 bathroom vacation retreat located in Madeira Beach. Under new ownership September 2019. All brand new furniture throughout, including new bedding & Tv's. Las Brisas #103 - You won't be disappointed with this wonderful beachfront 3 bedroom, 2 bathroom vacation retreat located in Madeira Beach. All brand new furniture throughout, including new bedding & TV's. Everything you need is here and just steps from the ocean, pool, spa, BBQ, including John's Pass Village just a short mile away. Free wifi included. You will be required .......

4.6 Star Review

You won't need to walk far to the beach from this beautiful condo! Located just steps from the beautiful gulf waters, this southern Madeira Beach 2 bedroom, 2 bath retreat is perfect for those looking for a memorable holiday Crimson on the Gulf #104 - You won't need to walk far to the beach from this beautiful condo! Located just steps from the beautiful gulf waters, this southern Madeira Beach 2 bedroom, 2 bath retreat is perfect for those looking for a memorable holiday! Stunning features throughout this 1,225 residence includes a spacious kitchen with granite countertops, modern lighting, a.......

4.0 Star Review

If you seek a vacation property within northern Madeira Beach with spectacular views, cool ocean breezes, and entertainment just a stone's throw away, look no further. This well appointed 3 bedroom, 2 bath condo, with large rooms, top amenities. Las Brisas #104 - If you seek a vacation property within northern Madeira Beach with spectacular views, cool ocean breezes, and entertainment just a stone's throw away, look no further. Las Brisas #104 is a well appointed 3 bedroom, 2 bath condo, with large rooms, top amenities and on call staff that are ready to assist you. You will be required to sig.......

4.5 Star Review

This is a well maintained 2 bedroom, 2 bathroom condo in sought after southern Madeira Beach and is a guest favorite! This 1,225 square foot residence is beautifully decorated. Crimson on the Gulf #105 - This is a well maintained 2 bedroom, 2 bathroom condo in sought after southern Madeira Beach and is a guest favorite! This 1,225 square foot residence is beautifully decorated and resembles something straight out of a Pottery Barn catalog. No detail has been overlooked. There is no phone in the condo. Free Wifi. Please note that lost keys will incur a replacement fee of $250, or the withholdin.......

4.3 Star Review

This ideally located 3 bedroom, 2 bath, corner unit condo has been completely renovated and updated. Just across the street from popular John's Pass Village, and overlooking the swimming pool, all with ocean views. Beach Place #106 - This ideally located 3 bedroom, 2 bath, corner unit condo has been completely renovated and updated. Just across the street from popular John's Pass Village, and overlooking the swimming pool, all with ocean views, visitors will appreciate everything this outstanding property offers. Free Wifi. This condo has 2 assigned parking spots. There is no additional parkin.......

4.5 Star Review

Charming 2 bedroom, 1.5 bath located steps from the beach and across from popular John's Pass Village offers great value!. This 940 square foot property provides everything you need to have a memorable vacation. The unit offers an open floor plan. Madeira Norte 106 - Beginning May 4, 2026, the pool will be shut down for approximately a month while the pool is being resurfaced.. Charming 2 bedroom, 1.5 bath located steps from the beach and across from popular John's Pass Village offers great value! Madeira Norte #106 is a 940 square foot property that provides everything you need to have a memo.......

4.5 Star Review

Located right at John's Pass, Madeira Beach this direct beach front 3 bedroom 2 bath has all the comforts of home with views that are sure to amaze you and your traveling companions. Relax on the beach front balcony. Beach Place #108 - Located right at John's Pass, Madeira Beach this direct beach front 3 bedroom 2 bath has all the comforts of home with views that are sure to amaze you and your traveling companions. Relax on the beach front balcony with access from the living area as well as the master bedroom. Open the windows and let the gentle sound of the Gulf surf soothe your soul. Updated.......

4.4 Star Review

If location is what you are looking for on your vacation in southern Madeira Beach, then 107 Beach Place is a great opportunity to live steps from the ocean waters. Enjoy breathtaking views from your own private balcony. Beach Place #107 - If location is what you are looking for on your vacation in southern Madeira Beach, then Beach Place #107 is a great opportunity to live steps from the ocean waters. Enjoy breathtaking views from your own private balcony surrounded by comfort in this 3 bedroom, 2 bath beachfront condo. This bright and open retreat has everything you need for an memorable vis.......

4.4 Star Review

2 Bedroom 1.5 Bath Beach View from Balcony. Updates throughout, located steps from the beach and across from popular John's Pass Village offers great value!. This 940 square foot property provides everything you need to have a memorable vacation. Madeira Norte 108 - Beginning May 4, 2026, the pool will be shut down for approximately a month while the pool is being resurfaced.. 2 Bedroom 1.5 Bath Beach View from Balcony. Updates throughout, located steps from the beach and across from popular John's Pass Village offers great value! Madeira Norte #108 is a 940 square foot property that provides .......

4.3 Star Review

There is too much to say about this exquisite 2 bedroom, 2 bath, 940 square foot property located in a prime location along southern Madeira Beach. From the moment you walk in, you will be entranced by this updated, beautifully decorated home. Madeira Norte #110 - Beginning May 4, 2026, the pool will be shut down for approximately a month while the pool is being resurfaced.. There is too much to say about Madeira Norte #110 exquisite 2 bedroom, 2 bath, 940 square foot property located in a prime location along southern Madeira Beach. From the moment you walk in, you will be entranced by this u.......

4.3 Star Review

2 bedroom 1 bath Surf Song Cottage - Ground floor. The cottage is a separate building apart from all other Surf Song Units. Located on the east side of the complex near the BBQ area 113 has a King in the master bedroom . Surf Song #113 - This is a 2 bedroom 1 bath Surf Song Cottage - Ground floor. The cottage is a separate building apart from all other Surf Song Units. Located on the east side of the complex near the BBQ area 113 has a King in the master bedroom and twin bunk beds and single bed in the guest bedroom. Should you have small children or over night guest there is a sleeper sofa in.......

4.4 Star Review

Imagine vacationing on your own private balcony watching dolphins swim along Madeira Beach. It's been known to happen when reserving this 2 bedroom,1.5 bathroom oceanfront condo. This 940 sq. ft. retreat offers everything you need for a wonderful vacation. Madeira Norte #111 - Beginning May 4, 2026, the pool will be shut down for approximately a month while the pool is being resurfaced.. Imagine vacationing on your own private balcony watching dolphins swim along Madeira Beach. It's been known to happen when reserving this 2 bedroom, 1.5 bathroom oceanfront condo. This 940 square foot retreat .......

4.0 Star Review

This quaint, adorable ground floor 2 bedroom, 2 bath unit is just steps away from the relaxing, heated swimming pool and patio area. With tropical decorations throughout, this non smoking residence has been recently updated for added comfort to our guests. Surf Song #114 - A quaint, adorable ground floor 2 bedroom, 2 bath unit, just steps away from the relaxing, heated swimming pool and patio area. With tropical decorations throughout, this non smoking residence has been updated for added comfort to our guests. Free Wifi. There is no phone in this unit. You will be required to sign a rental ag.......

4.4 Star Review

This cozy ground floor Studio efficiency is directly facing the beach and offers every amenity for a one of a kind Florida vacation. Perfect for a couple or family with one child, this studio includes breathtaking views of the tranquil heated swimming pool Surf Song #116 - This cozy ground floor Studio efficiency is directly facing the beach and offers every amenity for a one of a kind Florida vacation. Perfect for a couple or family with one child, this studio includes breathtaking views of the tranquil heated swimming pool and of course, some of Florida's most beautiful beaches - all just st.......

4.5 Star Review

Surf Song 117 is a ground floor non-smoking Studio Efficiency overlooking the pool and the beautiful gulf waters.This adorable property is popular for couples while offering one of a kind views! Free Wifi . Surf Song #117 - This unit is a ground floor non-smoking Studio Efficiency overlooking the pool and the beautiful gulf waters.. This adorable property is popular for couples while offering one of a kind views! Free Wifi. You will be required to sign a rental agreement with prior to a reservation being confirmed. Guests will immediately notice this well cared for property has new furnishings.......

4.5 Star Review

Enjoy this wonderful 2 bedroom, 2 bath poolside condo in sought after Madeira Beach. Nicely furnished and decorated, this ground floor property is literally just steps to the refreshing, heated swimming pool, BBQ facility and lounging area. Surf Song #118 - Enjoy this wonderful 2 bedroom, 2 bath poolside condo in sought after Madeira Beach. Nicely furnished and decorated, this ground floor property is literally just steps to the refreshing, heated swimming pool, BBQ facility and lounging area. Of course, the popular beaches are just a short walk away, as is John's Pass Village. Free Wifi. Plea.......

4.7 Star Review

You will feel like you’re on vacation the moment you step into this 2 bedroom, 2 bath poolside condo located on the ground floor. It has been recently updated with new furnishings, decor, and all new paint. Surf Song 119 - You will feel like you’re on vacation the moment you step into this 2 bedroom, 2 bath poolside condo located on the ground floor. It was fully renovated in 2025 while also saving some of its “old Florida” charm. This coastal retreat offers a living room that includes a spacious leather sectional along with a comfortable leather sitting chair to relax. Als.......

4.6 Star Review

Relax in this bright and airy 2 bedroom, 2 bath poolside condo, complete with brand new kitchen, new furnishings and flat screened panel TV! Just steps from the heated beach facing pool, and a quick walk to popular John's Pass Village. Surf Song #120 - Relax in this bright and airy 2 bedroom, 2 bath poolside condo, complete with brand new kitchen, new furnishings and flat screened panel TV! Just steps from the heated beach facing pool, and a quick walk to popular John's Pass, this ground unit condo has everything you need for the perfect vacation. The full kitchen provides all utensils for you.......

4.7 Star Review

Great opportunity to rent a beachfront property in popular Surf Song Resort in Madeira Beach! This 2 bedroom, 2 bath condo provides views, prime location, and everything you need to enjoy your stay at this sought after vacation resort. Free Wifi . Surf Song #121 - A Great opportunity to rent a beachfront property in popular Surf Song Resort in Madeira Beach! This 2 bedroom, 2 bath condo provides views, prime location, and everything you need to enjoy your stay at this sought after vacation resort. Free Wifi. Please note there is no phone in this condo. You will be required to sign a rental agr.......

4.6 Star Review

Spacious 1 bedroom, 1 bath rental property near everything, including popular John's Pass Village, white sandy beaches and heated, refreshing swimming pool! Although this unit has no balcony, you are still at Beach Place, directly on the beach! Beach Place #200 - #200 is a spacious 1 bedroom, 1 bath rental property near everything, including popular John's Pass Village, white sandy beaches and heated, refreshing swimming pool! Although this unit has no balcony and and only partial gulf view from bedroom, you are still at Beach Place, directly on the beach! Perfect for couples, guests can enjoy.......

4.1 Star Review