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Holmes Beach Waterfront Vacation Rentals, House Rentals & More - 213 Rentals Available.

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213 Vacation rentals

Filters applied: Waterfront

1 / 53

Holmes Beach House

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

$599.00

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from $599.00 / 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

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

(7)

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

$287.00

Excellent (7 reviews)

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from $287.00 / 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

1 / 19

Holmes Beach Townhouse

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500.00

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from $500.00 / night

(2)

1 / 19

Holmes Beach House

  • 5
  • 12
  • 4 nights min
  • Nearest beach 0.02 mi
  • Swimming pool
  • Child friendly

$800.00

Excellent (2 reviews)

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from $800.00 / 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

(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

(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 / 19

Holmes Beach House

  • 3
  • 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$600.00

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from $600.00 / 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)

1 / 49

Holmes Beach House

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

$699.00

Excellent (1 reviews)

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from $699.00 / night

Your search has been expanded 19.8 miles to include more rentals

(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 / 12

Ellenton Apartment - 14 miles away

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

$95.00

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from $95.00 / night

(27)

1 / 26

Treasure Island Cottage - 16.7 miles away

  • 1
  • 4
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“This was such a fun cottage to stay in for the week. It was very clean, had everything that we needed, and it was close to so many fun places in Treasure Island and Madeira Beach with John's Pass. Michael and Gitta made sure that we had everything...”
- Review left on 07/13/2016

$90.00

Very Good (27 reviews)

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from $90.00 / night

1 / 12

Bradenton House - 13.5 miles away

  • 5
  • 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$246.00

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from $246.00 / night

(11)

1 / 20

Bradenton House - 4.7 miles away

  • 3
  • 6
  • 7 nights min
  • Ask about children
  • Air conditioning
  • Pet friendly
“The location of this property is a perfect area. Just as described by the owner. House is fully equipped including a hand mixer. We enjoyed watching the water sports on the bay from the patio. Lots of parks and popular beaches within 5 mile radius...”
- Review left on 04/07/2017

$164.00

Very Good (11 reviews)

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from $164.00 / night

(12)

1 / 23

Treasure Island Condo - 17.1 miles away

  • 1
  • 4
  • 7 nights min
  • Nearest beach 0 mi
  • Swimming pool
  • Child friendly
“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

$83.00

Excellent (12 reviews)

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from $83.00 / night

(1)

1 / 31

Anna Maria Island Cottage - 3 miles away

  • 1
  • 3
  • min stay varies
  • Beach/lakeside relaxation

Responds fast! Avg. 3 hours 22 minutes

$224.00

Excellent (1 reviews)

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from $224.00 / night

(15)

1 / 57

Treasure Island Condo - 18.6 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 34 minutes

“We really enjoyed our stay at Whispers very much.The pool was great and it's a short walk to the beach. The owner was very nice and the rental was nicely kept and clean. Lots of amenities and kindness. Thanks so much for a great time...”
- Review left on 03/15/2017

$92.00

Very Good (15 reviews)

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from $92.00 / night

(1)

1 / 33

Anna Maria Island Villa - 3 miles away

  • 2
  • 3
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 22 minutes

$201.00

Excellent (1 reviews)

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from $201.00 / 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

(2)

1 / 47

Anna Maria House - 2.3 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)

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from $383.00 / night

(6)

1 / 17

Sarasota Apartment - 18.2 miles away

  • 1
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Car not necessary

Responds fast! Avg. 2 hours 25 minutes

“This was perfect for a 1 person quick getaway. It would also be great for an extended stay. Very clean and tastefully furnished. Easy walk to dining and shopping. Very easy drive to Sarasota attractions. But, once you're on Siesta, there's really no...”
- Review left on 02/24/2014

$229.00

Very Good (6 reviews)

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from $229.00 / night

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

(2)

1 / 41

Siesta Key Condo - 19.1 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“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

$295.00

Excellent (2 reviews)

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from $295.00 / night

(7)

1 / 15

Siesta Key House - 18.9 miles away

  • 4
  • 14
  • 7 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
“We used this house as a work retreat and a celebration! Overall, the house was perfect. Plenty of space, the views were awesome, the living room was great for a work meeting (5 people). The balconies were great. A good location...away from the town...”
- Review left on 01/23/2017

$982.00

Excellent (7 reviews)

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from $982.00 / night

1 / 49

Siesta Key House - 18.7 miles away

  • 4
  • 10
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$325.00

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from $325.00 / night

(57)

1 / 13

Longboat Key House - 6.9 miles away

  • 4
  • 10
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
“Great family vacation in a spacious and clean home with kids in their own rooms, full kitchen and close to the beach and to restaurants and activities. The January weather was awesome, 75-80 each day without rain.Likely return next year.Resort has...”
- Review left on 01/22/2017

$224.00

Very Good (57 reviews)

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from $224.00 / night

(2)

1 / 11

Cortez Cottage - 2.8 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.25 mi
  • Air conditioning
“This apartment had a beautiful open concept, nicely decorated. The place was supplied with nice quality furniture and cooking apparatus. Quiet and right on the canal, close to everything. Owners were above and beyond for help, and just a click...”
- Review left on 01/02/2015

$134.00

Very Good (2 reviews)

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from $134.00 / night

(1)

1 / 13

St. Petersburg Apartment - 19.8 miles away

  • 1
  • 2
  • 30 nights min
  • Ask about children
  • Air conditioning
“great location,location,location comfortable has everything you need just bring yourself and your swim suit freindly safe neigborhood area all kinds of events at the bay two blocks away this is our third year staying here started with one month now...”
- Review left on 04/06/2016

$39.00

Excellent (1 reviews)

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from $39.00 / night

1 / 63

Siesta Key House - 18.8 miles away

  • 6
  • 16
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$430.00

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from $430.00 / night

1 / 59

Sarasota Condo - 19.1 miles away

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

$155.00

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from $155.00 / 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

(14)

1 / 80

St. Petersburg Condo - 15.9 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 34 minutes

“Great place, Clean, Awesome room, and at a great location. This place is perfect for visiting St. Petersburg and the Gulf Beaches. Nearby Fort de Soto Park is one of our favorites and it has miles of fabulous beaches. Downtown St Pete is very close...”
- Review left on 03/24/2017

$147.00

Very Good (14 reviews)

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from $147.00 / night

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

(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)

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

(1)

1 / 38

St. Petersburg Apartment - 13.9 miles away

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

$85.00

Excellent (1 reviews)

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from $85.00 / night