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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 / 22

Madeira Beach Condo

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

$129

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from $129 / night

(2)

1 / 17

Madeira Beach Condo

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

(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

(6)

1 / 21

Madeira Beach Cottage

  • 1
  • 4
  • 3 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
“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 (6 reviews)

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from $85 / 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

(5)

1 / 10

Madeira Beach Condo

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

$285

Very Good (5 reviews)

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from $285 / 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

1 / 10

Madeira Beach Condo

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

from $250 / 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

(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

$114

Very Good (4 reviews)

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from $114 / night

1 / 27

Madeira Beach Condo

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

$136

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from $136 / night

1 / 22

Madeira Beach Condo

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

$129

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from $129 / 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

$100

Very Good (9 reviews)

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from $100 / night

1 / 18

Madeira Beach Condo

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

$129

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from $129 / night

(1)

1 / 24

Madeira Beach Apartment

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

$108

Excellent (1 reviews)

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from $108 / night

1 / 33

Madeira Beach Apartment

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

from $83 / night

1 / 20

Madeira Beach Studio

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

from $63 / night

1 / 26

Madeira Beach Apartment

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

from $143 / night

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(9)

1 / 18

Treasure Island Condo - 1.4 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Condo was beautiful, clean, comfortable and more spacious than similar priced options. Our favorite amenities were the beach chairs/mats and the washer/dryer. The location of the resort is outstanding with a walking score of 10! We enjoyed frequent...”
- Review left on 01/09/2017

$129

Excellent (9 reviews)

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from $129 / night

(24)

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 (24 reviews)

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from $119 / 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

(1)

1 / 30

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

(2)

1 / 16

Redington Shores House - 2.9 miles away

  • 5
  • 13
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“This house is an absolute beach paradise! The backyard with the heated pool and hot tub right beside the beach couldn't get any better. They were both clean and there were lots of toys and towels available. The house was very clean and well...”
- Review left on 02/26/2014

$715

Excellent (2 reviews)

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from $715 / night

(19)

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 (19 reviews)

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from $95 / night

(8)

1 / 26

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

$94

Very Good (8 reviews)

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from $94 / night

1 / 17

Indian Shores Condo - 3.2 miles away

  • 2
  • 4
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$136

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from $136 / night

(5)

1 / 16

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

$143

Excellent (5 reviews)

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from $143 / night

(43)

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 (43 reviews)

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from $128 / night

(15)

1 / 20

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

(5)

1 / 11

Indian Shores Condo - 3.4 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 (5 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
  • 4 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$125

Excellent (1 reviews)

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from $125 / night

(6)

1 / 16

Treasure Island Condo - 3.5 miles away

  • 1
  • 4
  • 4 nights min
  • 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

$125

Very Good (6 reviews)

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from $125 / night

1 / 15

Indian Shores House - 3.5 miles away

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

$129

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from $129 / night

1 / 23

Indian Shores Apartment - 3.5 miles away

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

from $160 / 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

$215

Excellent (20 reviews)

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from $215 / night

(4)

1 / 24

Indian Shores Condo - 4 miles away

  • 3
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We stayed here for the March break with our extended family. The pictures actually do not do it justice, it is very beautiful ! We are so happy to have lucked in to such a wonderful condo on the beach! The views are breath taking and the beach is...”
- Review left on 04/02/2016

$143

Excellent (4 reviews)

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from $143 / night

(21)

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

$168

Very Good (21 reviews)

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from $168 / night

(20)

1 / 19

Indian Shores Condo - 4.1 miles away

  • 2
  • 4
  • Min stay varies
  • 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

$93

Excellent (20 reviews)

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from $93 / night

1 / 84

Indian Shores House - 4.3 miles away

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

$800

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from $800 / night

(50)

1 / 43

Indian Shores Condo - 4.4 miles away

  • 2
  • 5
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“We rented this unit site unseen, very nervous about what we were walking into....As soon as we entered the condo we felt right at home. This unit is perfect, it was very clean and spacious. The owners were so helpful and answered all our questions...”
- Review left on 03/31/2016

$93

Very Good (50 reviews)

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from $93 / night

(3)

1 / 24

St. Pete Beach Condo - 4.4 miles away

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

$110

Excellent (3 reviews)

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from $110 / night

1 / 9

St. Pete Beach Condo - 4.4 miles away

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

$110

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from $110 / night

(11)

1 / 26

Treasure Island Condo - 4.4 miles away

  • 1
  • 3
  • Min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Car not necessary
“My wife and I stayed in Sunset Cove for 9 nights in December. It was the perfect home away from home with a VERY clean, neat condo just a 1 minute walk from the gorgeous Sunset Beach on Treasure Island. The location was perfect and the complex was...”
- Review left on 12/13/2016

$70

Excellent (11 reviews)

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from $70 / night

1 / 22

St. Pete Beach Condo - 4.5 miles away

  • 2
  • 6
  • Min stay varies
  • Nearest beach 0.04 mi
  • Swimming pool
  • Ask about children

$115

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from $115 / night

(13)

1 / 46

Treasure Island Condo - 4.5 miles away

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

$87

Excellent (13 reviews)

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from $87 / night

(8)

1 / 20

Treasure Island Condo - 4.6 miles away

  • 1
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Swedish cousins entrusted me to locate accommodations for their three week Florida vacation, and fortunately I found Lois's condo. Though I did not stay in the condo with them, I did visit three times, and this review is based on my observations and...”
- Review left on 04/30/2017

$139

Excellent (8 reviews)

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from $139 / night

(49)

1 / 21

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

$142

Excellent (49 reviews)

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from $142 / night

(14)

1 / 23

Treasure Island Condo - 4.6 miles away

  • 1
  • 4
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“My husband and I booked Florida last minute. Kevin was quick to respond to our emails and booking was easy. The day before we left I asked if we could have an early check in and it was no issue at all. We traveled to Florida from April 29-May 6/2016...”
- Review left on 05/14/2016

$87

Excellent (14 reviews)

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from $87 / night

1 / 13

Seminole Condo - 4.6 miles away

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

from $60 / night

(3)

1 / 32

Indian Shores Condo - 4.8 miles away

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

$95

Very Good (3 reviews)

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from $95 / night

(27)

1 / 14

Indian Shores Condo - 4.8 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“Right on the water with great view especially from the balcony. Lots of wildlife to view, even saw dolphins. House was well stocked with just about anything you would need. We stayed on the second floor and there is no elevator so you need to be...”
- Review left on 02/02/2017

$87

Very Good (27 reviews)

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from $87 / night

(10)

1 / 12

Indian Shores Townhouse - 4.8 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Beautiful condo, very well stocked, comfortable and cozy! We all loved it and would definitely consider renting it again if we come back to Florida! Thank you Rob...”
- Review left on 07/21/2015

$90

Excellent (10 reviews)

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from $90 / night

(6)

1 / 15

Indian Shores Condo - 5 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This condo is perfect for families with boats. The location is perfect to explore both Clearwater barrier islands and Treasure Island, Johns pass ect. We caught bait fish off the back dock and threw a crab trap off the dock and caught over a dozen...”
- Review left on 08/02/2016

$114

Excellent (6 reviews)

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from $114 / night

(10)

1 / 12

Indian Shores Condo - 5.1 miles away

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Let me begin by saying that I have never used a rent-by-owner program before. After this experience, I most definitely will, and hopefully to return to this lovely place. Jeannie was easy to communicate with, and everything was as expected when we...”
- Review left on 06/10/2015

$114

Excellent (10 reviews)

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from $114 / night