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Holmes Beach Vacation Rentals & House Rentals with Swimming Pool - 83 Rentals Available.

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83 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

$229.00

Very Good (7 reviews)

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from $229.00 / night

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(21)

1 / 11

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

$172.00

Very Good (21 reviews)

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from $172.00 / night

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Your search has been expanded 19.8 miles to include more rentals

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

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(6)

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 (6 reviews)

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from $682.00 / night

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(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

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1 / 32

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

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(3)

1 / 16

Bradenton House - 15.4 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 58 minutes

“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

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(7)

1 / 12

St. Petersburg Condo - 14.6 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

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Excellent (7 reviews)

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(2)

1 / 16

Sarasota Condo - 10.7 miles away

  • 2
  • 8
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool

Responds fast! Avg. 3 hours 21 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 (2 reviews)

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from $114.00 / night

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(62)

1 / 28

Treasure Island Condo - 17.1 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

$145.00

Excellent (62 reviews)

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from $145.00 / night

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(20)

1 / 28

St. Pete Beach Condo - 14.7 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 2 hours 53 minutes

“Donna was so easy to work with and their condo was very nice. The king master bed was so comfortable and their bedroom dresser was big enough for all our clothes. Great TV and comfortable sofa and side chairs. Kitchen was nicely equipped with...”
- Review left on 02/17/2019

$190.00

Excellent (20 reviews)

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from $190.00 / night

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(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

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(22)

1 / 15

Bradenton Condo - 13.5 miles away

  • 2
  • 6
  • 6 nights min
  • Nearest beach 8 mi
  • Swimming pool
  • Child friendly
“Anita and Joe were great hosts and wonderful people! The condo is in a secure location close to lots of entertainment, attractions, and shopping. The neighborhood was quiet and friendly with lots of exercise walkers and dog walkers. We spent most...”
- Review left on 02/02/2017

$144.00

Very Good (22 reviews)

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from $144.00 / night

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1 / 42

Madeira Beach Apartment - 19.8 miles away

  • 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

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1 / 34

St. Petersburg Condo - 13.9 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

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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

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(5)

1 / 41

Siesta Key Condo - 18.4 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 0.1 mi
  • Swimming pool
  • Child friendly

$175.00

Excellent (5 reviews)

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from $175.00 / night

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(25)

1 / 24

Sarasota Condo - 19.3 miles away

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

Responds fast! Avg. 2 hours 47 minutes

“Not only is the location perfect, but the condo is more then perfect! Everything we needed for a week at the beach including beach chairs... towels etc! Couldn't have been a better vacation! Can't wait to book again... THANKYOU STEVE...”
- Review left on 10/17/2017

$218.00

Excellent (25 reviews)

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from $218.00 / night

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1 / 45

Anna Maria Island Condo - 0.1 miles away

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

Responds fast! Avg. 2 hours 25 minutes

$344.00

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(7)

1 / 28

Treasure Island Condo - 18.3 miles away

  • 2
  • 5
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 12 minutes

“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

$148.00

Very Good (7 reviews)

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from $148.00 / night

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1 / 16

Lakewood Ranch Villa - 19.5 miles away

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

$153.00

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from $153.00 / night

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(23)

1 / 49

Anna Maria House - 1.5 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 43 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$287.00

Very Good (23 reviews)

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from $287.00 / night

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1 / 26

Bradenton Beach Villa - 1.7 miles away

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

Responds fast! Avg. 1 hour 35 minutes

$262.00

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from $262.00 / night

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(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

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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

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(31)

1 / 10

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

$148.00

Excellent (31 reviews)

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from $148.00 / night

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(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

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(1)

1 / 31

St. Petersburg Apartment - 14.1 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

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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

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1 / 59

Sarasota Condo - 19.1 miles away

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

Responds fast! Avg. 2 hours 35 minutes

$212.00

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from $212.00 / night

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(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

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(1)

1 / 36

St. Petersburg Apartment - 14 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

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(20)

1 / 108

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

$229.00

Excellent (20 reviews)

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from $229.00 / night

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(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

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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

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(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

$180.00

Excellent (4 reviews)

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from $180.00 / night

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(2)

1 / 47

Anna Maria House - 2.3 miles away

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

Responds fast! Avg. 1 hour 36 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

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1 / 20

Bradenton Beach Condo - 2.9 miles away

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

$655.00

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from $655.00 / night

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(25)

1 / 24

Bradenton House - 12.9 miles away

  • 4
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 15 mi
  • Swimming pool

Responds fast! Avg. 1 hour 48 minutes

“The location of this house is really outstanding. We enjoyed being on the river, watching the beautiful sunsets daily, watching birds come and go into the inlets. It is a private place within a lovely subdivision with lakes and riverfront. We also...”
- Review left on 02/02/2017

$150.00

Excellent (25 reviews)

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from $150.00 / night

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(27)

1 / 11

Bradenton House - 15.5 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 7 minutes

“The home was a great place for our group to stay. It was clean and well maintained. The location was ideal, close to golf courses and shopping and many good restaurants. We would definitely stay there again. The owner, Larry was very good to work...”
- Review left on 02/01/2017

$241.00

Excellent (27 reviews)

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from $241.00 / night

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