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Holmes Beach Vacation Rentals & House Rentals with Swimming Pool - 193 Rentals Available.

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193 Vacation rentals

Filters applied: Swimming pool

1 / 53

Holmes Beach House

  • 6
  • 14
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$499.00

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from $499.00 / night

(2)

1 / 25

Holmes Beach Townhouse

  • 4
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$299.00

Excellent (2 reviews)

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from $299.00 / night

(6)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • 3 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

$250.00

Excellent (6 reviews)

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from $250.00 / night

1 / 34

Holmes Beach House

  • 5
  • 10
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

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from $399.00 / night

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199.00

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from $199.00 / night

1 / 24

Holmes Beach House

  • 4
  • 10
  • 4 nights min
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$750.00

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from $750.00 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“We enjoyed this house. It was just a short walk to the beach. It was the perfect size for our family of four. The decorations were very pretty and beachy! The pool and outside landscaping was gorgeous! It came supplied with a beach wagon which was a...”
- Review left on 04/21/2016

$500.00

Excellent (2 reviews)

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from $500.00 / night

1 / 24

Holmes Beach House

  • 4
  • 8
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$700.00

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from $700.00 / night

(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

$150.00

Very Good (21 reviews)

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from $150.00 / night

(2)

1 / 19

Holmes Beach House

  • 5
  • 12
  • min stay varies
  • Nearest beach 0.02 mi
  • Swimming pool
  • Child friendly

$500.00

Excellent (2 reviews)

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from $500.00 / night

1 / 19

Holmes Beach House

  • 3
  • 8
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$259.00

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from $259.00 / night

(1)

1 / 49

Holmes Beach House

  • 6
  • 12
  • min stay varies
  • Nearest beach 0.01 mi
  • Swimming pool
  • Child friendly

$599.00

Excellent (1 reviews)

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from $599.00 / night

1 / 18

Holmes Beach House

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

$259.00

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from $259.00 / night

1 / 33

Holmes Beach House

  • 3
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$200.00

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from $200.00 / night

(3)

1 / 27

Holmes Beach House

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

$166.00

Excellent (3 reviews)

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from $166.00 / night

1 / 21

Holmes Beach House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$129.00

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from $129.00 / night

1 / 33

Holmes Beach House

  • 1
  • 2
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$125.00

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from $125.00 / night

Your search has been expanded 19.1 miles to include more rentals

1 / 13

Lakewood Ranch House - 17.1 miles away

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

$243.00

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from $243.00 / night

(12)

1 / 26

Treasure Island Condo - 17.3 miles away

  • 1
  • 3
  • min stay varies
  • Nearest beach 0 mi
  • Swimming pool
  • Car not necessary

Responds fast! Avg. 2 hours 56 minutes

“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

$75.00

Excellent (12 reviews)

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from $75.00 / night

(2)

1 / 16

Sarasota Condo - 10.7 miles away

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

$99.00

Very Good (2 reviews)

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from $99.00 / 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

(3)

1 / 41

Siesta Key Condo - 18.4 miles away

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

$143.00

Excellent (3 reviews)

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from $143.00 / night

(2)

1 / 47

Anna Maria House - 2.3 miles away

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

$334.00

Excellent (2 reviews)

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from $334.00 / night

(27)

1 / 11

Bradenton House - 15.5 miles away

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

$210.00

Excellent (27 reviews)

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from $210.00 / night

1 / 43

Sarasota House - 17.1 miles away

  • 5
  • 12
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 2 hours 58 minutes

$325.00

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from $325.00 / night

(1)

1 / 8

Sarasota Condo - 10.7 miles away

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

$55.00

Very Good (1 reviews)

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from $55.00 / night

1 / 40

Siesta Key House - 18.4 miles away

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

Responds fast! Avg. 2 hours 58 minutes

$381.00

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from $381.00 / night

(6)

1 / 12

St. Petersburg Condo - 14.6 miles away

  • 2
  • 4
  • 30 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

$100.00

Excellent (6 reviews)

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from $100.00 / night

(6)

1 / 40

Bradenton House - 16.1 miles away

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

$125.00

Excellent (6 reviews)

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from $125.00 / 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

$100.00

Excellent (3 reviews)

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from $100.00 / night

1 / 20

Palma Sola House - 5 miles away

  • 6
  • 19
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$293.00

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from $293.00 / night

(12)

1 / 47

Treasure Island Condo - 18.6 miles away

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

Responds fast! Avg. 3 hours 39 minutes

“We enjoyed everything about Whispers. It was very clean,beautifully decorated as were all the condos each with its own theme. Ours was the Artist theme.It was very quiet, private and the heated pool and the dock were wonderful - we spent a lot of...”
- Review left on 05/05/2017

$115.00

Very Good (12 reviews)

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from $115.00 / night

(1)

1 / 31

St. Petersburg Apartment - 14.1 miles away

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

$70.00

Excellent (1 reviews)

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from $70.00 / night

(1)

1 / 33

St. Petersburg Apartment - 14 miles away

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

$70.00

Excellent (1 reviews)

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from $70.00 / night

1 / 46

St. Petersburg Condo - 13.9 miles away

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

$84.00

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from $84.00 / night

(1)

1 / 35

St. Petersburg Apartment - 14.1 miles away

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

$80.00

Excellent (1 reviews)

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from $80.00 / night

(1)

1 / 37

St. Petersburg Apartment - 14.1 miles away

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

$70.00

Excellent (1 reviews)

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from $70.00 / night

1 / 37

St. Petersburg Condo - 14.1 miles away

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

$80.00

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from $80.00 / night

1 / 12

Sarasota Apartment - 18.1 miles away

  • 2
  • 1
  • 89 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$107.00

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from $107.00 / night

1 / 12

Sarasota Apartment - 14.9 miles away

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

$104.00

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from $104.00 / night