Madeira Beach Vacation Rentals with Private Pool

(13 rentals)
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Madeira Beach Condo
2 BR | 2 BA | Sleeps 7 | Quick View
Sleeps 7, 2 bedrooms, 2 bathrooms
3 reviews

$226

avg/night

$226
avg per night
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Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

*The pool is currently not working due to the hurricanes. Please reach out to us to confirm it is working before you book if that will be an issue*This 5th floor 2 bedroom / 2 bathroom condo welcomes you with coastal vibes of total relaxation and complete comfort by offering every amenity. The spacious ...

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Property Type

Madeira Beach Condo

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Madeira Beach Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
16 reviews

$264

avg/night

$264
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • WiFi

About this property

Our pictures are from several of our street front condominiums. Our personal website will show you all of the pictures of each unit that we offer for rent. All of our units that end in 1,2 & 3 are over looking Gulf Blvd and floors 3, 4 and 5 have views of our intercoastal waterways. These luxury 2 ...

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Property Type

Madeira Beach Condo

Featured review

"The amazing condo"

Hi we would like to say that the condo we rented owned by Diane Sullivan from NL was an extremely top of the line one cleanliness well stocked again thanks Diane and the office staff were very friendly ...

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Madeira Beach House
1 BR | 1 BA | Sleeps 2 | Quick View
Sleeps 2, 1 bedroom, 1 bathroom

Distance to beach: 500 feet to Archibald Park's Madeira Beach - Snack Shack

$140

avg/night

$140
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Experience the ultimate coastal escape in our 1-bedroom Executive Waterfront Penthouse. This is highest end/nicest unit in Madeira Beach, 1st floor, no steps, water is 10' from the lanai, amazing K bed, private custom showers, gourmet kitchen, condo is 20' from club house, walk everywhere, nestled ...

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Property Type

Madeira Beach House

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Madeira Beach Condo
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom
10 reviews

$152

avg/night

$152
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • Rentals by owner
  • WiFi

About this property

This is a beautifully furnished condominium with two bedrooms, dining room furniture and private balcony accessible from living room. The unit has two TVs, regular cable in the bedroom on a 26" screen and premium digital multimedia service with 14 HBO channels and 12 Cinemax channels in the living ...

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Property Type

Madeira Beach Condo

Featured review

"Enjoyable stay"

Beautiful accommodations with everything one would want to have an enjoyable vacation. Very close to the beach just a short walk. In addition very close to retail outlets and restaurants. The owner is ...

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Madeira Beach Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$300

avg/night

$300
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Discover the epitome of coastal elegance in our 2-bedroom, 2-bathroom Executive Waterfront Condo. This is highest end/nicest unit in Madeira Beach, 1st floor, no steps, water is 10' from the lanai, amazing K beds, private custom showers, gourmet kitchen, condo is 20' from club house, walk ...

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Property Type

Madeira Beach Condo

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Madeira Beach Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$194

avg/night

$194
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

SUNRISE AND SUNSET. 30 day minimum rental period per association rules. No Exceptions. Coffee in the morning with sunrise, drinks in the evening with sunsets are standard with this spacious 3 BR 2 BA Gulf front end unit. Rare to get both views from your PRIVATE wrap around balcony with 16 ft. facing ...

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Property Type

Madeira Beach Condo

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Madeira Beach Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
9 reviews

$515

avg/night

$515
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool

About this property

Welcome to our huge newly renovated luxury condo on Madeira Beach. Trillium 3C is a modern and stylish condo that offers the perfect blend of comfort and luxury for your next beach getaway.This condo is in an awesome location, within a short walk from John's Pass that offers great nightlife with ...

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Property Type

Madeira Beach Condo

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Madeira Beach House
3 BR | 2.5 BA | Sleeps 12 | Quick View
Sleeps 12, 3 bedrooms, 2.5 bathrooms
2 reviews

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Have FUN with the whole family or with a group of your close friends. Sunbathers Casa is spacious. Madeira Beach is 6 min away. Professionally decorated interior and a showstopper backyard with a huge heated pool. Sunbathers Casa is immaculately cleaned between guests. Clearwater and St. Petersburg, just ...

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Property Type

Madeira Beach House

Featured review

"Excellent space!"

It was so very hot and humid when we stayed but the outdoor space made it so enjoyable. It also had alot of area to have some privacy too! Would definitely stay there again, Amy was great!

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Madeira Beach Condo | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
18 reviews

$556

avg/night

$556
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Experience the ultimate beachfront getaway at our stunning condo on Maderia Beach. Enjoy breathtaking ocean views, direct beach access, and a luxurious, modern interior. Relax by the pool, soak up the sun on the white sandy beach, or explore the vibrant local area. Perfect for a romantantic escape or ...

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Property Type

Madeira Beach Condo

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Madeira Beach Bungalow
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
5 reviews

$225

avg/night

$225
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Cutest eclectic place you will ever see. If you are working away from home or just needing a break, come relax at the Old Oak Beach Bungalow. A landmark in the front yard to gaze at in the morning while having your coffee on the font porch or relaxing on the side jasmine covered veranda in the hammock ...

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Property Type

Madeira Beach Bungalow

Featured review

"What a Gem!"

Yes, eclectic is the word. Very artsy/flossy and super clean. Equipped with anything you would ever need. Very easy check in and host was extremely responsive. Location to restaurants, stores, and beach ...

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Madeira Beach Condo | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$258

avg/night

$258
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

CORNER CONDO WITH A 60 FOOT "L" SHAPE BALCONY!! Locate right on Madeira Beach. Overlooking the heated salt water pool and the white sands off the Gulf of Mexico.

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Property Type

Madeira Beach Condo

Featured review

"Awesome time! We definitely will be back!"

This beautiful condo is spotlessly clean and well equipped. The owner is very accommodating and will help out in any way he can. The condo building is well maintained. The pool is warm and clean. Last but ...

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Madeira Beach Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

$143

avg/night

$143
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

$100.00 will hold this unit , payment due in full 30 days before arrival. Seven day minimum, but will rent out three nights in between other rentals, if available . This property is rented by regulars Nov-April every year so only available May-October, thanks in advanced ! This beachfront rental has ...

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Property Type

Madeira Beach Condo

Featured review

"Good time!"

Rental was right on the beach. Balcony was huge and we were able to watch manatee and dolphins in the water. Pool was awesome and very clean. We enjoyed a great vacation!

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Madeira Beach House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 500 feet to Madeira Beach

$245

avg/night

$245
avg per night
View Details

Key Amenities

  • Air conditioning
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Single Family Home located on the intercostal water of Boca Ciega Bay. Fish off the dock in the back yard along side the inground pool and just steps from the Gulf beach out the front door. There is a spacious master bedroom with a king bed and a second smaller bedroom with two twin beds. Two full ...

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Property Type

Madeira Beach House

Featured review

"Great stay!!"

Such a wonderful house and wow, the pool on the inlet is amazing!! Sunrises were gorgeous from the dock. House has everything you need for the stay. Bed was very comfy and nice updated bathrooms. Location ...

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Madeira Beach Vacation Rentals