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Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 66 Rentals Available.

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66 Vacation rentals

Filters applied: Swimming pool

(3)

1 / 27

Madeira Beach Condo

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

$180.00

Excellent (3 reviews)

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from $180.00 / night

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(4)

1 / 14

Madeira Beach Condo

  • 2
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Enjoyed the vacation. Rented 2 condos for family of10 for the week of July 4. Nice rooms, great beach, and amazing 4th of July fireworks on the beach from 8:30 until nearly 11:00. never seen fireworks like that before...”
- Review left on 07/18/2015

$201.00

Very Good (4 reviews)

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from $201.00 / night

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(1)

1 / 27

Madeira Beach Condo

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

$156.00

Excellent (1 reviews)

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from $156.00 / night

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1 / 19

Madeira Beach Condo

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$148.00

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from $148.00 / night

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1 / 22

Madeira Beach Condo

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

$148.00

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from $148.00 / night

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(24)

1 / 33

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$180.00

Very Good (24 reviews)

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from $180.00 / night

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(1)

1 / 25

Madeira Beach Condo

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

$238.00

Excellent (1 reviews)

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from $238.00 / night

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(10)

1 / 15

Madeira Beach Townhouse

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 30 mi
  • Swimming pool

Responds fast! Avg. 2 hours 51 minutes

“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

$140.00

Very Good (10 reviews)

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from $140.00 / night

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(2)

1 / 13

Madeira Beach Condo

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 1 hour 4 minutes

$164.00

Excellent (2 reviews)

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from $164.00 / night

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1 / 25

Madeira Beach Condo

  • 1
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

$107.00

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from $107.00 / night

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1 / 23

Madeira Beach Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$172.00

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from $172.00 / night

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1 / 29

Madeira Beach Apartment

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

$98.00

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from $98.00 / night

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1 / 26

Madeira Beach Condo

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

$98.00

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from $98.00 / night

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1 / 26

Madeira Beach Apartment

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

$150.00

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from $150.00 / night

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(1)

1 / 35

Madeira Beach Condo

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$133.00

Excellent (1 reviews)

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from $133.00 / night

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1 / 37

Madeira Beach Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$130.00

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from $130.00 / night

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1 / 41

Madeira Beach Condo

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

$113.00

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from $113.00 / night

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1 / 29

Madeira Beach Studio

  • -1
  • 2
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$105.00

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from $105.00 / night

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Your search has been expanded 19.3 miles to include more rentals

(6)

1 / 12

Clearwater Condo - 8.6 miles away

  • 2
  • 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 16 mi
  • Swimming pool
“My brother and I stayed here for one week, it was in the middle of everything, clean and quiet. Three heated swimming pools and laundry on site which was convenient for us too. All in all very nice...”
- Review left on 03/06/2017

$189.00

Excellent (6 reviews)

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from $189.00 / night

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(21)

1 / 79

Clearwater Condo - 10.4 miles away

  • 1
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This condo was perfect. Close to everything, restaurants, grocery store and the Clearwater Ferry is about 2 miles away with free parking. It takes you right to the Clearwater Harbor which is right at Clearwater Beach. Nice 10 min. boat ride. The...”
- Review left on 08/13/2017

$171.00

Very Good (21 reviews)

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from $171.00 / night

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(20)

1 / 120

St. Petersburg Condo - 8.7 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Swimming pool

Responds fast! Avg. 1 hour 57 minutes

“We had stayed all around Florida , but Never had a view like this, water everywhere, from all the windows. When you see the pictures they are gorgeous but in real life Wow. I think this is one of the best condo's we have stayed in. The owners are...”
- Review left on 05/30/2017

$229.00

Excellent (20 reviews)

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from $229.00 / night

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(5)

1 / 24

Indian Shores Condo - 3.1 miles away

  • 2
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This condo is very large, having a breakfast nook with plenty of lighting, a living room, dining room, two bathrooms, two bedrooms and a large enough to eat on balcony overlooking the Gulf. We enjoy the weekly appetizer parties where we watch the...”
- Review left on 03/09/2016

$148.00

Excellent (5 reviews)

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from $148.00 / night

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(1)

1 / 24

St. Petersburg Manor house - 10.2 miles away

  • 5
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$1,718.00

Excellent (1 reviews)

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from $1,718.00 / night

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(25)

1 / 28

Indian Shores Condo - 4.1 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Great location and great place! Would only recommend 6 people, however, because the last bed is in the family room...”
- Review left on 01/07/2017

$291.00

Very Good (25 reviews)

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from $291.00 / night

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(1)

1 / 27

Tampa House - 19.2 miles away

  • 4
  • 10
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$315.00

Excellent (1 reviews)

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from $315.00 / night

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(5)

1 / 13

Treasure Island Condo - 4.5 miles away

  • 1
  • 4
  • 5 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 1 hour 28 minutes

$109.00

Excellent (5 reviews)

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from $109.00 / night

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(8)

1 / 17

St. Petersburg Condo - 8.3 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning
“We thoroughly enjoyed our stay in this beautiful condo overlooking Boca Ciega Bay.. Very clean, comfortable home, what a nice view of the bay with dolphins regularly swimming by! The owner, Ken, was stellar to deal with, all our needs were totally...”
- Review left on 05/21/2016

$86.00

Excellent (8 reviews)

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from $86.00 / night

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(2)

1 / 36

Dunedin House - 17.2 miles away

  • 1
  • 2
  • 30 nights min
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 28 minutes

$69.00

Very Good (2 reviews)

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from $69.00 / night

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(36)

1 / 26

Clearwater Condo - 11.5 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The condo is a beautiful and an impeccable place at a prime and convenient location. My husband, 3 children, and my parents stayed here and have such high regards and compliments for this fabulous vacation spot! The owners were wonderful in...”
- Review left on 08/16/2017

$526.00

Excellent (36 reviews)

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from $526.00 / night

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(3)

1 / 24

Clearwater Condo - 10.2 miles away

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

$344.00

Excellent (3 reviews)

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from $344.00 / night

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(25)

1 / 28

St. Pete Beach Condo - 7.3 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 1 hour 59 minutes

“Donna was so easy to work with and their condo was very nice. The king master bed was so comfortable and their bedroom dresser was big enough for all our clothes. Great TV and comfortable sofa and side chairs. Kitchen was nicely equipped with...”
- Review left on 02/17/2019

$250.00

Excellent (25 reviews)

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from $250.00 / night

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(7)

1 / 28

Treasure Island Condo - 3.4 miles away

  • 2
  • 5
  • 7 nights min
  • 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

$205.00

Very Good (7 reviews)

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from $205.00 / night

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(20)

1 / 50

Treasure Island Condo - 4.5 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 15 minutes

“We absolutely loved our stay at sunset cove. The condo is very clean and has everything you could possibly need. Plenty of room for 2 adults and 2 teen girls. The location is great very close to restaurants and activities. We will definitely be...”
- Review left on 01/09/2017

$115.00

Excellent (20 reviews)

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from $115.00 / night

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(2)

1 / 36

Indian Shores House - 3.5 miles away

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

$172.00

Average (2 reviews)

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from $172.00 / night

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(79)

1 / 26

Treasure Island Condo - 4.6 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“First and foremost, Nick was easily the most wonderful owner we have ever dealt with. He was quick to get back with us on any email and very pleasant. The condo is perfectly located on the beach, minutes from everything and walking distance to Caddy'...”
- Review left on 04/05/2017

$169.00

Excellent (79 reviews)

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from $169.00 / night

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(1)

1 / 13

St. Pete Beach Condo - 5.6 miles away

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

$210.00

Very Good (1 reviews)

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from $210.00 / night

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1 / 30

Clearwater Condo - 10.2 miles away

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$350.00

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from $350.00 / night

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(44)

1 / 43

Indian Shores Condo - 3.2 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 2 hours 22 minutes

“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

$199.00

Very Good (44 reviews)

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from $199.00 / night

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(8)

1 / 37

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

$167.00

Very Good (8 reviews)

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from $167.00 / night

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(2)

1 / 72

Anna Maria House - 19.3 miles away

  • 2
  • 6
  • 2 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Air conditioning

$418.00

Excellent (2 reviews)

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from $418.00 / night

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