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Holmes Beach Vacation Rentals & House Rentals with Swimming Pool - 99 Rentals Available.

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99 Vacation rentals

Filters applied: Swimming pool

(7)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Five of us and two dogs spent last week of July here, Great location, 8 iron golf shot to the beach from front yard, fantastic pool in back yard complete with all the toys you need for the beach or pool in garage, also refrigerator in garage to save...”
- Review left on 08/27/2015

$230.00

Very Good (7 reviews)

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from $230.00 / night

(21)

1 / 17

Holmes Beach Townhouse

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$184.00

Very Good (21 reviews)

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from $184.00 / night

Your search has been expanded 19.8 miles to include more rentals

1 / 37

St. Petersburg Apartment - 14.1 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

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from $72.00 / night

(6)

1 / 40

Bradenton House - 16.1 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 25 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 24 minutes

“As soon as I unlocked the door to this property and looked in, I turned to my wife and said, "you're definitely going to be impressed" and needless to say she was!The home was by far the best we ever rented and I would have even rated it higher than...”
- Review left on 06/17/2016

$111.00

Excellent (6 reviews)

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from $111.00 / night

(3)

1 / 16

Bradenton House - 15.4 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly
“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$144.00

Excellent (3 reviews)

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from $144.00 / night

1 / 81

Anna Maria Island Condo - 2.4 miles away

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

$396.00

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from $396.00 / night

1 / 26

Bradenton House - 5.2 miles away

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

$165.00

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from $165.00 / night

(2)

1 / 25

Siesta Key Condo - 19.1 miles away

  • 2
  • 5
  • 7 nights min
  • Nearest beach 0.09 mi
  • Swimming pool
  • Ask about children
“Our stay at Siesta Palms was great. The condo was very clean and up to date. We enjoyed the beautiful pool and proximity to the beach. The owners couldn't have been kinder or more accommodating. I highly recommend this condo...”
- Review left on 04/15/2016

$304.00

Excellent (2 reviews)

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from $304.00 / night

(34)

1 / 16

Sarasota Guest house - 15.5 miles away

  • 1
  • 2
  • 7 nights min
  • Swimming pool
  • Car not necessary
  • Air conditioning
“My husband and I stayed in Joyce and Jeff's beautiful guest apartment for two weeks. Everything was perfect inside and out. The property was immaculate and the owners included extra touches that went above and beyond. While we spent most of our time...”
- Review left on 08/09/2017

$131.00

Excellent (34 reviews)

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from $131.00 / night

(1)

1 / 30

St. Petersburg Condo - 13.9 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)

1 / 38

St. Petersburg Apartment - 14.1 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

1 / 46

St. Petersburg Condo - 13.9 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

(7)

1 / 23

Siesta Key House - 19 miles away

  • 4
  • 12
  • 7 nights min
  • Nearest beach 0.2 mi
  • Swimming pool
  • Child friendly

$682.00

Excellent (7 reviews)

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from $682.00 / night

(12)

1 / 40

Siesta Key Condo - 19.4 miles away

  • 2
  • 6
  • 14 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“Great place! Everything was wonderful,beach was a short walk away. Love all the new addition to public beach. Pool was heated,we went swimming every day. Unit was very clean and comfortable,couldn't ask for a better place. Took the free taxi to...”
- Review left on 01/06/2017

$90.00

Excellent (12 reviews)

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from $90.00 / night

(9)

1 / 17

Sarasota Condo - 19.1 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We had such a wonderful trip to Siesta Key! The condo was very nice. Beautifully decorated, very clean, and great location! Everything from booking it to checking out was very easy. Everything we needed was available to us, and more! Everybody...”
- Review left on 08/02/2016

$152.00

Excellent (9 reviews)

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from $152.00 / night

1 / 16

Bradenton House - 8.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$189.00

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from $189.00 / night

(1)

1 / 33

St. Petersburg Apartment - 14.1 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

(3)

1 / 11

Sarasota Condo - 14.9 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Ask about children
“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$104.00

Excellent (3 reviews)

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from $104.00 / night

(4)

1 / 32

St. Petersburg Apartment - 13.9 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$85.00

Excellent (4 reviews)

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from $85.00 / night

1 / 32

St. Petersburg Apartment - 14 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 3 mi
  • Swimming pool
  • Child friendly

$72.00

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from $72.00 / night

1 / 16

Lakewood Ranch Villa - 19.5 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 19 mi
  • Swimming pool
  • Ask about children

Responds fast! Avg. 3 hours 47 minutes

$153.00

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from $153.00 / night

(1)

1 / 13

Lakewood Ranch House - 17.1 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

Average (1 reviews)

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from $279.00 / night

(2)

1 / 41

Treasure Island Condo - 19.2 miles away

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

$287.00

Excellent (2 reviews)

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from $287.00 / night

(5)

1 / 19

Siesta Key Condo - 19.1 miles away

  • 1
  • 4
  • min stay varies
  • Nearest beach 0.09 mi
  • Swimming pool
  • Child friendly
“Thank you for a wonderful week! The room was beautiful and Mary Ann and staff were all so accommodating to anything that you may need! We would highly recommend Siesta Palms to everyone! We are looking forward to coming back as soon as possible,...”
- Review left on 07/13/2016

$258.00

Excellent (5 reviews)

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from $258.00 / night

(1)

1 / 13

St. Pete Beach Condo - 16.2 miles away

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

$202.00

Very Good (1 reviews)

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from $202.00 / night

(12)

1 / 23

Bradenton House - 15.4 miles away

  • 3
  • 6
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“My stay was from July 2- July 16 and I absolutely loved it. The rooms and bathrooms were super clean. Kitchen has all the appliances you needed it, home came with shower towels and amazing air conditioning through the vents. The neighborhood was...”
- Review left on 07/17/2016

$279.00

Excellent (12 reviews)

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from $279.00 / night

1 / 36

St. Petersburg Apartment - 14.2 miles away

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

$82.00

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from $82.00 / night

1 / 42

Madeira Beach Apartment - 19.8 miles away

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

$252.00

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from $252.00 / night

(3)

1 / 16

Sarasota Condo - 10.7 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Responds fast! Avg. 2 hours 33 minutes

“We rented this two bedroom listed as a Condo, it is really two adjoining hotel rooms with kitchenettes. Nice accommodations, however the shower heads could be a little higher not convenient for taller people. Great view, right on Marina, close to the...”
- Review left on 01/23/2015

$114.00

Very Good (3 reviews)

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from $114.00 / night

(2)

1 / 10

Siesta Key Condo - 19.4 miles away

  • 1
  • 4
  • 14 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“FIVE STARS!!!!! Terry the owner is a great guy that insured our stay in his condo went well. The condo has a great location just a couple of blocks from the Siesta Key Beach. The condo has everything you need for a great beach experience. The...”
- Review left on 01/24/2017

$87.00

Excellent (2 reviews)

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from $87.00 / night

1 / 37

St. Petersburg Condo - 14.1 miles away

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

$82.00

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from $82.00 / night

1 / 15

Bradenton House - 7.7 miles away

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 57 minutes

$343.00

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from $343.00 / night

(1)

1 / 33

St. Petersburg Apartment - 14 miles away

  • 2
  • 6
  • 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 / 26

Bradenton Beach Villa - 1.7 miles away

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

$262.00

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from $262.00 / night

(1)

1 / 34

St. Petersburg Condo - 14.1 miles away

  • 2
  • 5
  • 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)

1 / 25

St. Petersburg Apartment - 14 miles away

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

$114.00

Excellent (1 reviews)

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from $114.00 / night

(20)

1 / 117

St. Petersburg Condo - 14 miles away

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

1 / 8

Sarasota Condo - 10.7 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

Responds fast! Avg. 2 hours 33 minutes

$57.00

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from $57.00 / night

(3)

1 / 34

Bradenton Condo - 15.3 miles away

  • 2
  • 6
  • 3 nights min
  • Nearest beach 12 mi
  • Swimming pool
  • Child friendly

$144.00

Excellent (3 reviews)

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from $144.00 / night

(4)

1 / 19

Bradenton Villa - 16.1 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“House was a great location for our Needs. Very Clean and spacious. Heated Pool was a great asset.. Would have liked a bigger more useable grill...”
- Review left on 02/23/2017

$207.00

Excellent (4 reviews)

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from $207.00 / night