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Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 82 Rentals Available.

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82 Vacation rentals

Filters applied: Swimming pool

(3)

1 / 27

Madeira Beach Condo

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

$152.00

Excellent (3 reviews)

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from $152.00 / 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

$172.00

Very Good (4 reviews)

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from $172.00 / night

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(1)

1 / 27

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

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1 / 19

Madeira Beach Condo

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

$161.00

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from $161.00 / night

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1 / 22

Madeira Beach Condo

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

$152.00

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from $152.00 / 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

$152.00

Very Good (24 reviews)

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from $152.00 / night

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(1)

1 / 25

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

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(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

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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. 2 hours 34 minutes

$213.00

Excellent (2 reviews)

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from $213.00 / night

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1 / 20

Madeira Beach Condo

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

$149.00

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from $149.00 / night

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1 / 25

Madeira Beach Condo

  • 1
  • 4
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

$95.00

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from $95.00 / night

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1 / 14

Madeira Beach Condo

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

$229.00

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from $229.00 / night

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1 / 21

Madeira Beach Condo

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$258.00

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from $258.00 / night

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1 / 24

Madeira Beach Apartment

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

$90.00

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from $90.00 / night

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1 / 22

Madeira Beach Condo

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

$90.00

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from $90.00 / night

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1 / 23

Madeira Beach Apartment

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

$151.00

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from $151.00 / night

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1 / 35

Madeira Beach Condo

  • 3
  • 7
  • 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
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$120.00

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from $120.00 / night

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1 / 29

Madeira Beach Studio

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

$106.00

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from $106.00 / night

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Your search has been expanded 19.2 miles to include more rentals

(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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(6)

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 (6 reviews)

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from $189.00 / night

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(5)

1 / 10

Clearwater House - 13.5 miles away

  • 3
  • 10
  • 1 night min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 1 hour 13 minutes

“Loved vacationing at the Margaritaville Pool home. The inside is soooo cute and decorated with beachy accents throughout. The kitchen is fully stocked with everything you need to cook with. We loved the screened porch and ate most of our meals there....”
- Review left on 10/03/2015

$487.00

Excellent (5 reviews)

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from $487.00 / 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. 51 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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(21)

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

Very Good (21 reviews)

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from $144.00 / night

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(1)

1 / 84

Indian Shores House - 4.3 miles away

  • 6
  • 22
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$801.00

Excellent (1 reviews)

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from $801.00 / night

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1 / 24

St. Petersburg Manor house - 10.2 miles away

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$1,145.00

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from $1,145.00 / 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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(40)

1 / 27

Clearwater Condo - 11.5 miles away

  • 3
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.1 mi
  • Swimming pool
“Just back from a week stay with our family of 4. Stunning views we saw dolphins most days in the bay . Beautifully spacious apartment that was a welcome relief to come back to its air conditioned rooms after a hot day out at the beach...”
- Review left on 08/05/2016

$315.00

Excellent (40 reviews)

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from $315.00 / night

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(20)

1 / 50

Treasure Island Condo - 4.5 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 39 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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(3)

1 / 43

Redington Beach Manor house - 0.1 miles away

  • 5
  • 13
  • 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

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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

$320.00

Excellent (36 reviews)

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from $320.00 / night

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(20)

1 / 23

Indian Rocks Beach Condo - 7 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 50 minutes

“A very enjoyable 3 weeks in a most comfortable condo right on the beach. The 4th floor unit had a wonderful view of the beach and Gulf. The unit was updated and very well done. Within walking distance of some nice restaurants and watering holes...”
- Review left on 10/03/2016

$150.00

Very Good (20 reviews)

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from $150.00 / night

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(8)

1 / 17

St. Petersburg Condo - 8.3 miles away

  • 2
  • 4
  • 2 nights min
  • Swimming pool
  • Air conditioning
  • Pet friendly
“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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1 / 42

Clearwater Apartment - 11.5 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 16 minutes

$164.00

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from $164.00 / 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. 2 hours 14 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

$228.00

Excellent (20 reviews)

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from $228.00 / night

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(2)

1 / 15

Indian Shores House - 3.5 miles away

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

$144.00

Average (2 reviews)

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from $144.00 / night

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(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

$225.00

Very Good (24 reviews)

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from $225.00 / night

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(17)

1 / 16

Indian Rocks Beach Condo - 5.2 miles away

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

Responds fast! Avg. 2 hours 34 minutes

“Absolutely loved this place! Great week with four adults and 2 babies. Great accommodations! Clean, well stocked, wonderful views! Nice beach, not crowded, nice pool! Usually stay in SC. This was way better. Ocean calm, no jellyfish, white sand....”
- Review left on 08/22/2016

$213.00

Very Good (17 reviews)

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from $213.00 / night

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(3)

1 / 24

Clearwater Apartment - 11.5 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

Responds fast! Avg. 2 hours 52 minutes

$180.00

Excellent (3 reviews)

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from $180.00 / night

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(1)

1 / 43

Clearwater Condo - 11.5 miles away

  • 3
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 8 minutes

$258.00

Excellent (1 reviews)

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from $258.00 / night

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