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Madeira Beach Vacation Rentals with Private Pool

(24 rentals)
Madeira Beach House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

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

Key Amenities

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

About this property

Discover the epitome of coastal elegance in our 2-bedroom, 2-bathroom Executive Waterfront Condo, ideally located at Madellion Blvd in the heart of Maderia Beach, FL 33708. This penthouse exudes a sense of tranquility and sophistication, offering a spacious and inviting retreat for up to 6 guests.This...

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Featured review

"Amazing Place and Area"

This place is absolutely perfect exclamation the condo has luxurious Marriott king size pillow top beds make it hard to get up in the morning, I fully stocked kitchen and everything you need, and a beautiful...

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$242
avg per night
Madeira Beach Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Special Savings Already Applied — No Code Needed**Welcome to Seaview 201, a direct beachfront condo rental in Madeira Beach that delivers space, light, and panoramic Gulf views you simply don’t get in typical vacation rentals. This rare corner unit offers over 1,500 square feet of bright,...

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$450
avg per night
Madeira Beach Condo
Sleeps 8, 2 bedrooms, 2 bathrooms
7 reviews

Key Amenities

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

About this property

**Newly Remodeled Modern Bright and Spacious– SEAVIEW #405 ** SPECIAL MARCH 14-24, 2026- PRICE HAS BEEN REDUCED TO REFLECT DISCOUNT ️ BEACHFRONT CORNER CONDO | SEAVIEW 405 | MADEIRA BEACH Just 15 minutes to St. Pete beach Welcome to Seaview 405, a newly remodeled, gulf-front corner condo...

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Featured review

"updated and clean rental"

Very nice, modern & clean rental. Location was fantastic. Managers very helpful with great service. For instance, I couldn't find the code to get in when I arrived & I reached out. The response was...

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$499
avg per night
Madeira Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.*Stunning Renovated Beachfront Condo | 3 Bed, 2 Bath | Gulf Views | Madeira BeachWelcome to your dream vacation getaway! This beautifully updated 3-bedroom, 2-bath condo is in the heart of Madeira Beach. Our condo building has just undergone...

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$473
avg per night
Madeira Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.*Wake up to the sound of the waves and end your day with spectacular Gulf sunsets at Seaview 204, a spacious 3-bedroom, 2-bath beachfront condo in the heart of beautiful Madeira Beach, Florida. Perfect for families or groups, this bright and...

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$474
avg per night

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Madeira Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
17 reviews

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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Featured review

"We're Back!"

So excited to be here this week and see all the New Touches at Collwood. New Resident Managers, New Pool and Pool furniture, New Barbeque grills, New landscaping, and a whole New Attitude that compliments...

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$332
avg per night
Madeira Beach Condo
Sleeps 9, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.**Welcome to your perfect beach escape in Madeira Beach! Located on the 5th floor of a quiet, exclusive 25-unit beachfront building, this beautifully maintained 3-bedroom, 2-bath condo offers unmatched panoramic views of the Gulf of Mexico...

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$458
avg per night
Madeira Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

️ Spacious | Updated Comfort | Perfect for Families, Snowbirds & Group GetawaysWelcome to Seaview Unit 302, your fully equipped Madeira Beach vacation rental where the sand is just steps away and the views are unforgettable. This 3-bedroom, 2-bathroom beachfront condo rental offers the perfect...

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$466
avg per night
Madeira Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.* Seaview #104 | Spacious 3BR Condo w/ Gulf Views, Heated Pool & Hot Tub ️ 1st Floor (Second Level) | Oversized Balcony | King Beds | Walk to EverythingWelcome to Seaview Unit #104, your home away from home in beautiful Madeira...

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$487
avg per night
Madeira Beach Condo
Sleeps 4, 1 bedroom, 1 bathroom

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

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Experience the ultimate coastal escape in our elegant ground-floor 1-bedroom Executive Waterfront Penthouse, perfectly situated in beautiful Madeira Beach. Designed for couples seeking a luxurious and romantic getaway, this exquisite retreat offers easy access—no stairs to navigate with luggage...

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$185
avg per night
Madeira Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
5 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.** Seaview 504 – Top-Floor 2BR Oceanfront Condo with Gulf Views + Pool & Hot TubFully renovated, oceanfront, and perfectly located — Seaview 504 is the ultimate beach retreat. This top-floor 2-bedroom, 2-bath condo sits...

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Featured review

"Beautiful View"

We enjoyed our stay at Seaview Condos. Great view of the Gulf! Step right out to the beach, had all the amenities. The pool and hot tub were a bonus. We will book again if possible!

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$453
avg per night
Madeira Beach Condo
Sleeps 7, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.**Seaview 305...PARADISE… On a beautiful stretch of private, white sandy beach in the western Gulf of Mexico, this is simply a fabulous vacation getaway!Our 3rd floor 2 bedroom / 2 bath oceanfront corner unit will welcome you...

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Featured review

"Wonderful! Felt like home!"

Very cozy spot, great view and nice furnishings. This isn't a cheap furnished rental, its got nice towels, coffee maker, bedding and more. I stay at a lot of STR and this is one of the nicer furnished homes....

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$442
avg per night
Madeira Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.**Seaview 404: Beachfront Getaway on the 4th Floor in Madeira Beach, FLWelcome to Seaview 404, a spacious 3-bedroom, 2-bath beachfront condo on the 4th floor, offering stunning views of the Gulf of Mexico! This comfortable retreat is...

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Featured review

"Beautiful view!"

This condo was perfect for our family vacation. Kitchen was fully stocked with all that we needed. The balcony was very large and had a stunning view. Perfect location and nice pool area. Would recommend...

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$467
avg per night
Madeira Beach Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

️ Fully Renovated | Oceanfront Balcony | Sleeps 5 Comfortably Welcome to Seaview #301, a stunning 2-bedroom, 2-bathroom beachfront condo rental in the heart of Madeira Beach, Florida. Beautifully furnished and thoughtfully designed, this third-floor retreat combines modern style with the unbeatable...

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Featured review

"Holiday on the beach"

Apartment was really good, overlooking the beach, It will be better when the new office is nearer to pick up and drop off for the key, apartment was clean and had everything you needed in it except no...

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$473
avg per night
Madeira Beach Condo
Sleeps 7, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

**Our building is open and all amenities are fully functional.**Step into Seaview 105, a beautifully remodeled 2-bedroom, 2-bath condo where modern elegance meets beachfront bliss. This first floor/second level retreat offers easy access to the beach and a huge private balcony, giving you the ultimate...

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$472
avg per night
Madeira Beach Condo
Sleeps 8, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

I take terrible pictures, condo looks even better in person! Master bedroom and Living room have an ocean front balcony directly overlooking the Gulf of Mexico. There are 3 bedrooms and 2 full baths, a full kitchen and large living room. Our Spacious (1470 sq/ft), fully air-conditioned unit sleeps...

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Featured review

"Rental review"

The apartment was amazing. It had everything you could ask for or want for golf. Front views were spectacular. The bedding was comfortable, but definitely stay here again.

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$390
avg per night
Madeira Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

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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$217
avg per night
Special Offer
Madeira Beach Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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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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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$451
avg per night
Madeira Beach House
Sleeps 4, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 500 feet to Madeira Beach

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 a queen size bed. Two full...

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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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$245
avg per night
Madeira Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
24 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

HURRICAINE UPDATE: After a long couple of months, our pool and elevator are finally back up and running!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...

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$542
avg per night
Madeira Beach Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
11 reviews

Key Amenities

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

About this property

$200 per weekl 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...

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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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$186
avg per night
Madeira Beach Condo
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Paradise awaits you at this Direct Gulf Front 3 bedroom 2 bath condo in Las Brisas. During your stay, you’ll awake to the beautiful white sands of the Gulf of Mexico and enjoy memorable sunsets every evening with views from your balconies off the Living area and the Master Bedroom! This unit has...

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$576
avg per night
Madeira Beach Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
40 reviews

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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$549
avg per night
Madeira Beach Condo
Sleeps 3, 1 bedroom, 1.5 bathrooms

Key Amenities

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

About this property

This is a lovely, one bedroom with king-size bed, 2nd floor condo with waterfront view located in the highly desired Madeira Beach Yacht Club. It is just across the road to the beautiful white sand beach. The condo is close to many amenities including the Winn-Dixie Liquor Store, CVS Drug Store, the post...

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$92
avg per night
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