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Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 18 Rentals Available.

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18 Vacation rentals

Filters applied: Swimming pool

1 / 10

Madeira Beach Condo

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

from $128 / night

(9)

1 / 15

Madeira Beach Townhouse

  • 2
  • 4
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
“I have stayed at Townhouse 343 for several years and have recommended it to several of my friends and co-workers. Neither I, nor any of my friends have ever been disappointed. The owners are hospitable and think of every detail to make your stay...”
- Review left on 10/08/2016

$87

Very Good (9 reviews)

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from $87 / night

(2)

1 / 41

Madeira Beach Condo

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We stayed three nights and had a great time aside from the cool temps on Sunday when we left. The condo was wonderful and being able to get in early after a long night of flying was so nice. We would recommend this condo to anyone. Everything you...”
- Review left on 02/27/2017

$110

Excellent (2 reviews)

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from $110 / night

(7)

1 / 16

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We were so happy to open the door to our unit and find it so nice! It was clean beautifully decorated and had all the basic things you would need. Our balcony was located to the side of the building but we can still see the beach and the Gulf and...”
- Review left on 10/28/2016

$100

Very Good (7 reviews)

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from $100 / night

(5)

1 / 10

Madeira Beach Condo

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We loved our stay at Holiday Villas III. Very clean condo and accommodated our family of 4! There was always chairs available at the pool to use and the beach was not crowded. Room 305 was upgraded, had comfortable beds, reasonably priced, and was...”
- Review left on 07/25/2016

$114

Very Good (5 reviews)

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from $114 / night

(4)

1 / 31

Madeira Beach Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great condo. Screened in large porch is perfect for sitting/eating out bug free. Great beach. Water is warm, calm and beautiful. We found many sandollars, starfish and saw dolphins almost every day. Would go back again...”
- Review left on 08/05/2016

$129

Excellent (4 reviews)

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from $129 / night

(13)

1 / 28

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“I highly recommend this unit, it was well maintained. It was beautifully decorated and the kitchen and bathrooms are unbelievable. No complaints and would stay in this exact unit again!!..views of the Gult are outstanding”
- Review left on 03/01/2017

$129

Very Good (13 reviews)

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from $129 / night

(1)

1 / 10

Madeira Beach Condo

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We enjoyed our stay at this rental. It had everything we needed, the location provided walking distance to almost everything...”
- Review left on 07/01/2016

$107

Excellent (1 reviews)

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from $107 / night

(9)

1 / 8

Madeira Beach Cottage

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Newly renovated with one bedroom queen and two sleepers. One bath and fully equipped kitchen. No dishwasher and on site laundry is very clean. Direct beach access and trolley stopsl Very well maintained private pool. BBQ grill area very clean. We...”
- Review left on 08/30/2016

$95

Very Good (9 reviews)

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from $95 / night

(24)

1 / 16

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Gulf front condo in Madeira Beach; location/view is outstanding and condo was fully equipped. Convenient to restaurants, shopping and attractions. Only two complaints were the carpet in unit was dirty, stained and worn and needed to be cleaned or...”
- Review left on 11/28/2016

$129

Very Good (24 reviews)

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from $129 / night

1 / 21

Madeira Beach Condo

  • 3
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

from $160 / night

(3)

1 / 20

Madeira Beach Cottage

  • 1
  • 4
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“i stayed in this darling cottage for nearly 4 months and it felt like home. cottage is decorated with lots of color and beachy cheer, has a little porch, private yard and cute picket fence, with parking just outside the fence and a friendly coffee...”
- Review left on 01/31/2017

$85

Excellent (3 reviews)

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from $85 / night

(2)

1 / 17

Madeira Beach Condo

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We stayed at Sand Dollar 102 and loved it! It was very spacious, gulf front and we saw beautiful sunsets. The condo was well maintained and had everything we needed. The location is good and we found plenty to do. I definitely would stay here again...”
- Review left on 01/24/2016

$128

Excellent (2 reviews)

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from $128 / night

(2)

1 / 13

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We have stayed here twice and like the unit. Clean up to date, although the bed in the main bedroom is a bit out of date. We like the pool area being open all the time. I do wish the balcony was not screened since it inhibits the airflow. All in all...”
- Review left on 08/19/2016

$125

Very Good (2 reviews)

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from $125 / night

1 / 26

Madeira Beach Apartment

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

from $140 / night

1 / 24

Madeira Beach Apartment

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $108 / night

1 / 33

Madeira Beach Apartment

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $79 / night

1 / 20

Madeira Beach Studio

  • -1
  • 3
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $72 / night

Your search has been expanded 3.9 miles to include more rentals

1 / 39

Redington Beach House - 0.1 miles away

  • 7
  • 23
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1299

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from $1299 / night

(2)

1 / 45

North Redington Beach Condo - 1.9 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We just stayed in #603 for a week with 4 of our children and it was simply amazing! It truly was the PERFECT place to take the kids (ages 9, 9, 12 and 18) for a week to enjoy the beach and pool. The condo has literally every single thing that you can...”
- Review left on 07/14/2015

$136

Excellent (2 reviews)

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from $136 / night

(2)

1 / 25

North Redington Beach Condo - 1.9 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We got a great deal on this property in August. The unit was clean, all appliances, etc in working order. The decor was comfortable and accommodations above expectations. Great view facing the ocean. The beach is nice and pool was clean. Our...”
- Review left on 08/29/2016

$114

Very Good (2 reviews)

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from $114 / night

(23)

1 / 20

Treasure Island Condo - 2.4 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.05 mi
  • Swimming pool
“We stayed at Sunset Vista, and it was great. The condo was exactly as shown in pictures. We really enjoyed it. It had everything you would need to make a vacation fantastic...”
- Review left on 02/21/2017

$119

Excellent (23 reviews)

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from $119 / night

(1)

1 / 29

Treasure Island Condo - 2.4 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$171

Excellent (1 reviews)

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from $171 / night

(12)

1 / 24

Treasure Island Condo - 2.4 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The condo at Sunset Vistas was beautiful! We stayed in room 401. Kathy was really helpful in getting us booked. The view of the ocean was spectacular, breathtaking sunsets every evening. The property was immaculate & the staff was super friendly....”
- Review left on 03/19/2017

$159

Excellent (12 reviews)

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from $159 / night

(4)

1 / 12

Redington Shores Condo - 2.9 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Quiet beachfront location with excellent view of beautiful sunsets. Great beach, clean condo with all kitchen tools needed. Appreciated the starter set of soap and paper supplies, even coffee. Master bath small and living room could use another...”
- Review left on 10/30/2016

$157

Very Good (4 reviews)

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from $157 / night

(3)

1 / 15

Treasure Island Condo - 2.9 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is beautiful! We want our all for ourselves! The location is prime and the view is amazing. We will book again...”
- Review left on 11/26/2016

$104

Very Good (3 reviews)

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from $104 / night

(17)

1 / 37

Redington Shores Condo - 3 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Loved this condo. Clean accommodations with a great beach view with easy access and great location to restaurants. The owner was professional and courteous. Loved my vacation...”
- Review left on 06/01/2016

$95

Excellent (17 reviews)

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from $95 / night

(8)

1 / 28

Indian Shores Condo - 3.1 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Everything was as advertised and promised. The condition of the unit was tip top. Loved the abundance of dishes, tableware, and cookware in the new kitchen. The maintenance of the public areas and pool was very good. Two small downers--light...”
- Review left on 11/27/2015

$105

Very Good (8 reviews)

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from $105 / night

(5)

1 / 15

Indian Shores Condo - 3.2 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My wife and I stayed the week of labor day 2016. The condo was very clean and well maintained. It was also conveniently located so you could get across the inter costal on to the main land. Shopping for food was a 10 minute drive if that. The owners...”
- Review left on 09/12/2016

$158

Excellent (5 reviews)

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from $158 / night

(44)

1 / 35

Indian Shores Condo - 3.2 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We loved this place! So wonderful to have lots of room with a heated pool and hot tub so close to the Bay...”
- Review left on 12/09/2016

$128

Very Good (44 reviews)

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from $128 / night

(15)

1 / 16

Treasure Island Condo - 3.3 miles away

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Thoroughly enjoyed our month at this clean, convenient and comfortable condo! It is within easy walking distance of the beach and many restaurants as well as the Publix and Walgreens. The view of Boca Ciega Bay from the 2nd floor balcony is beautiful...”
- Review left on 02/04/2017

$114

Excellent (15 reviews)

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from $114 / night

(2)

1 / 12

Indian Rocks Beach Condo - 3.3 miles away

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The complex is right on the beach. Most everything was described accurately. We are a family of 8 and finding a place for all of us to stay is sometimes a challenge. My one complaint may be my own ignorance, considering this was my first experience...”
- Review left on 04/21/2016

$114

Very Good (2 reviews)

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from $114 / night

(7)

1 / 9

Indian Rocks Beach Condo - 3.3 miles away

  • 2
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The condo was great....very modern and nicely decorated....it was very clean and we didn't even turn the air on with temps in the low to muddle 80's we just opened the windows and let the breeze blow thru. I absolutely loved the balcony sitting out...”
- Review left on 05/09/2016

$104

Very Good (7 reviews)

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from $104 / night

(4)

1 / 10

Indian Shores Condo - 3.3 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We recently stayed two weeks at this condo and had a wonderful time. The condo was clean, well-equipped and the view was incredible! Our air conditioning quit working on a Saturday and the owners were very responsive and had a repair person...”
- Review left on 03/19/2017

$115

Excellent (4 reviews)

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from $115 / night

(7)

1 / 28

Treasure Island Condo - 3.4 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The location is perfect! Your backyard is the bay. Morning Views are breathtaking!!!! My husband fished there every morning and every night. (condo has 3 fishing poles, a few beach chairs and towels) The beach is a short walk away. Publix is right...”
- Review left on 01/03/2017

$129

Very Good (7 reviews)

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from $129 / night

(1)

1 / 22

Treasure Island Condo - 3.5 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$114

Excellent (1 reviews)

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from $114 / night

(6)

1 / 16

Treasure Island Condo - 3.5 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“I saw this Appartment online and decided it would be suitable for my wife and I to stay while visiting Treasure Island. It was a great choice . The Appartment was clean and everything we needed. We stayed for 2 weeks and just walking out the door...”
- Review left on 05/29/2016

$114

Very Good (6 reviews)

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from $114 / night

1 / 23

Indian Shores Apartment - 3.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

from $150 / night

1 / 20

Treasure Island Studio - 3.9 miles away

  • -1
  • 3
  • 3 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$105

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from $105 / night

(20)

1 / 15

Treasure Island House - 3.9 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We had such a great time. Beautiful home, quiet, saw Dolphins, our son and husband fished and we enjoyed the pool and hottub.also close to everything. We definitely would recommend and will be back. It was a great vacation...”
- Review left on 08/17/2016

$227

Excellent (20 reviews)

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from $227 / night