Search 105,200+ Vacation Rentals
✕

Madeira Beach Cabin Rentals & Beach Rentals with Swimming Pool - 123 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

123 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)

Book

from $152.00 / night

Book

(10)

1 / 8

Madeira Beach Cottage

  • 1
  • 2
  • min stay varies
  • 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)

Book

from $115.00 / night

Book

(12)

1 / 21

Madeira Beach Cottage

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

Responds fast! Avg. 2 hours 19 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)

Book

from $98.00 / night

Book

(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)

Book

from $148.00 / night

Book
1 / 27

Madeira Beach Condo

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

$164.00

Book

from $164.00 / night

Book
1 / 19

Madeira Beach Condo

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

$258.00

Book

from $258.00 / night

Book
1 / 22

Madeira Beach Condo

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

$152.00

Book

from $152.00 / night

Book

(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)

Book

from $118.00 / night

Book

(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)

Book

from $229.00 / night

Book
1 / 18

Madeira Beach Condo

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

$152.00

Book

from $152.00 / night

Book

(1)

1 / 13

Madeira Beach Condo

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

$180.00

Excellent (1 reviews)

Book

from $180.00 / night

Book
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

Book

from $229.00 / night

Book
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

Book

from $315.00 / night

Book
1 / 21

Madeira Beach Condo

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

$264.00

Book

from $264.00 / night

Book
1 / 15

Madeira Beach Condo

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

$287.00

Book

from $287.00 / night

Book
1 / 19

Madeira Beach Condo

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

$93.00

Inquire

from $93.00 / night

Inquire
1 / 33

Madeira Beach Apartment

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

$93.00

Inquire

from $93.00 / night

Inquire

(1)

1 / 24

Madeira Beach Apartment

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

$98.00

Excellent (1 reviews)

Inquire

from $98.00 / night

Inquire
1 / 20

Madeira Beach Studio

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

$75.00

Inquire

from $75.00 / night

Inquire
1 / 27

Madeira Beach Apartment

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

$155.00

Inquire

from $155.00 / night

Inquire

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. 3 hours 14 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)

Book

from $199.00 / night

Book

(1)

1 / 36

Indian Rocks Beach House - 6.7 miles away

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

$205.00

Very Good (1 reviews)

Book

from $205.00 / night

Book

(1)

1 / 40

Indian Rocks Beach House - 6.8 miles away

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

$171.00

Excellent (1 reviews)

Book

from $171.00 / night

Book

(23)

Certificate of Excellence

1 / 19

Clearwater House - 14.1 miles away

  • 5
  • 6
  • 1 night min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 27 minutes

Certificate of Excellence

“Ellen was wonderful, her home beautiful, accommodations were comfortable and just what we needed! Ellen was helpful with suggestions for beaches and offered discounts for area attractions...”
- Review left on 04/20/2016

$98.00

Excellent (23 reviews)

Book

from $98.00 / night

Book

(1)

1 / 41

Indian Rocks Beach House - 6.2 miles away

  • 4
  • 12
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$228.00

Excellent (1 reviews)

Book

from $228.00 / night

Book

(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 22 minutes

$383.00

Excellent (2 reviews)

Book

from $383.00 / night

Book

(21)

1 / 14

Indian Shores Condo - 4.1 miles away

  • 2
  • 4
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“We just returned from two glorious weeks at this property. The weather was fantastic, the location was just a short walk across the road to the beach. It was very clean and well taken care of, the beds were comfortable. The condo was a short...”
- Review left on 10/25/2016

$100.00

Excellent (21 reviews)

Inquire

from $100.00 / night

Inquire

(6)

1 / 30

Treasure Island Condo - 2.8 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Lovely place to stay! Everything you could want. We have spent several yrs. in Treasure Island and this is the beast place to stay...”
- Review left on 03/16/2017

$225.00

Excellent (6 reviews)

Inquire

from $225.00 / night

Inquire

(9)

1 / 35

Clearwater House - 13.3 miles away

  • 3
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We loved the property. Very clean and well maintained. The house is located in a well kept subdivision on the North Shore of Clearwater beach. It was a short walk to the beach, short distance to tourist attractions and still private enough to enjoy...”
- Review left on 07/19/2016

$217.00

Very Good (9 reviews)

Book

from $217.00 / night

Book

(3)

1 / 20

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)

Book

from $1,145.00 / night

Book

(36)

1 / 24

Clearwater Condo - 11.5 miles away

  • 3
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 1 hour 13 minutes

“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

$259.00

Excellent (36 reviews)

Book

from $259.00 / night

Book

(6)

1 / 12

St. Petersburg Condo - 8.3 miles away

  • 2
  • 4
  • min stay varies
  • 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

Inquire for Rates

Excellent (6 reviews)

Inquire

Pricing unknown

Inquire
1 / 33

Clearwater House - 11 miles away

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

$573.00

Book

from $573.00 / night

Book

(16)

1 / 19

Indian Rocks Beach Condo - 7 miles away

  • 3
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“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

$225.00

Very Good (16 reviews)

Inquire

from $225.00 / night

Inquire

(5)

1 / 22

Clearwater Condo - 12.6 miles away

  • 1
  • 4
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The Camelot is not like any place I've ever stayed. It is very comfortable and feels a lot like home. The staff was very friendly and helpful, and made us feel like old friends even tho we had never met before. It is clean and well maintained, you...”
- Review left on 05/08/2016

$137.00

Average (5 reviews)

Book

from $137.00 / night

Book

(2)

1 / 12

Indian Rocks Beach Condo - 5.2 miles away

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My family had a blast when we stayed at this condo. It was well stocked with everything we needed. We were a simple walk to the beach plus the pool was clean. The drive to johns pass for dinner was easy plus there were restaurants close by. We will...”
- Review left on 07/20/2016

$287.00

Very Good (2 reviews)

Book

from $287.00 / night

Book

(1)

1 / 13

St. Pete Beach Condo - 5.6 miles away

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

$202.00

Very Good (1 reviews)

Book

from $202.00 / night

Book
1 / 36

St. Petersburg Apartment - 8.2 miles away

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

$82.00

Inquire

from $82.00 / night

Inquire

(1)

1 / 30

St. Petersburg Condo - 8.6 miles away

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

$72.00

Excellent (1 reviews)

Inquire

from $72.00 / night

Inquire
1 / 46

St. Petersburg Condo - 8.4 miles away

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

$86.00

Inquire

from $86.00 / night

Inquire