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Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 119 Rentals Available.

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119 Vacation rentals

Filters applied: Swimming pool

(2)

1 / 27

Madeira Beach Condo

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

$152.00

Excellent (2 reviews)

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from $152.00 / night

(10)

1 / 8

Madeira Beach Cottage

  • 1
  • 2
  • 3 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary

Responds fast! Avg. 35 minutes

“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

$115.00

Very Good (10 reviews)

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from $115.00 / night

(12)

1 / 21

Madeira Beach Cottage

  • 1
  • 4
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 25 minutes

“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

$98.00

Excellent (12 reviews)

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from $98.00 / night

(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

$148.00

Very Good (4 reviews)

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from $148.00 / night

1 / 27

Madeira Beach Condo

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

$164.00

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from $164.00 / night

1 / 19

Madeira Beach Condo

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

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from $258.00 / night

1 / 22

Madeira Beach Condo

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

$152.00

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from $152.00 / night

(24)

1 / 30

Madeira Beach Condo

  • 2
  • 6
  • min stay varies
  • 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

$229.00

Very Good (24 reviews)

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from $229.00 / 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

$118.00

Very Good (9 reviews)

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from $118.00 / night

(1)

1 / 18

Madeira Beach Condo

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

$152.00

Excellent (1 reviews)

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from $152.00 / night

(1)

1 / 13

Madeira Beach Condo

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

Responds fast! Avg. 3 hours 41 minutes

$180.00

Excellent (1 reviews)

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from $180.00 / night

1 / 20

Madeira Beach Condo

  • 1
  • 3
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$138.00

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from $138.00 / night

1 / 14

Madeira Beach Condo

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

$172.00

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from $172.00 / night

1 / 28

Madeira Beach Condo

  • 2
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$201.00

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from $201.00 / night

1 / 42

Madeira Beach Apartment

  • 2
  • 8
  • 3 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$229.00

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from $229.00 / night

1 / 12

Madeira Beach Apartment

  • 2
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 30 minutes

$315.00

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from $315.00 / night

1 / 21

Madeira Beach Condo

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

$264.00

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from $264.00 / night

1 / 15

Madeira Beach Condo

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

$287.00

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from $287.00 / night

1 / 33

Madeira Beach Apartment

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

$93.00

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from $93.00 / night

1 / 19

Madeira Beach Condo

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

$100.00

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from $100.00 / night

(1)

1 / 24

Madeira Beach Apartment

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

$105.00

Excellent (1 reviews)

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from $105.00 / night

1 / 20

Madeira Beach Studio

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

$75.00

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from $75.00 / night

1 / 27

Madeira Beach Apartment

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

$155.00

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from $155.00 / night

Your search has been expanded 19.3 miles to include more rentals

(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 35 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

(5)

1 / 12

Clearwater Condo - 8.6 miles away

  • 2
  • 4
  • 1 night min
  • Nearest beach 16 mi
  • Swimming pool
  • Child friendly
“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 (5 reviews)

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from $189.00 / night

(1)

1 / 36

Indian Rocks Beach House - 6.7 miles away

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$274.00

Very Good (1 reviews)

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from $274.00 / night

(24)

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

$221.00

Very Good (24 reviews)

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from $221.00 / night

(2)

1 / 13

Treasure Island Condo - 4.5 miles away

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

Responds fast! Avg. 3 hours 1 minutes

$104.00

Very Good (2 reviews)

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from $104.00 / night

(2)

1 / 47

Anna Maria House - 19.3 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 9 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

(3)

1 / 38

Redington Beach Manor house - 0.1 miles away

  • 5
  • 12
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This home was amazing. We brought three generations and had plenty of space--both for together times and when we wanted privacy! Three teenage girls enjoyed the privacy of the garage suite. We called it the bachelorette pad! The pool and patio area...”
- Review left on 10/22/2017

$1,145.00

Excellent (3 reviews)

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from $1,145.00 / night

(6)

1 / 36

Clearwater House - 13.9 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“7 girlfriends spent s wwek celebrating our birthdays! We had everything possible at the house from cooking to relaxing. House is beautifully decorated; comfy beds; great pool and close enough to walk to beach. Great restaurants in Clesrwster and...”
- Review left on 11/06/2016

$450.00

Excellent (6 reviews)

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from $450.00 / night

(1)

1 / 21

Clearwater House - 11 miles away

  • 5
  • 15
  • 1 night min
  • Swimming pool
  • Child friendly
“This site was excellent for a family reunion. Sleeping 13 was very comfortable. Site was clean, comfortable, nice pool, and 3 minutes to beach. Would highly recommended for a family gahering...”
- Review left on 08/15/2016

$831.00

Excellent (1 reviews)

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from $831.00 / night

1 / 22

North Redington Beach Condo - 1.9 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children

$155.00

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from $155.00 / night

1 / 33

Clearwater House - 11 miles away

  • 4
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$630.00

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from $630.00 / night

(20)

1 / 79

Clearwater Condo - 10.4 miles away

  • 1
  • 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$144.00

Excellent (20 reviews)

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from $144.00 / night

(10)

1 / 37

Clearwater Villa - 12.9 miles away

  • 10
  • 28
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We absolutely loved this place! It had everything we needed and reasonably priced! Just a few steps to the beach, stores and restaurants close by. My son absolutely loved it and none of us wanted to leave. We plan on coming back in the future....”
- Review left on 06/24/2016

$343.00

Very Good (10 reviews)

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from $343.00 / night

(1)

1 / 31

St. Petersburg Apartment - 8.2 miles away

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

$72.00

Excellent (1 reviews)

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from $72.00 / night

(1)

1 / 36

St. Petersburg Apartment - 8.5 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$72.00

Excellent (1 reviews)

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from $72.00 / night

1 / 46

St. Petersburg Condo - 8.4 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$85.00

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from $85.00 / night

(1)

1 / 38

St. Petersburg Apartment - 8.2 miles away

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

$82.00

Excellent (1 reviews)

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from $82.00 / night