Search 105,200+ Vacation Rentals
✕

Holmes Beach Vacation Rentals & House Rentals with Swimming Pool - 16 Rentals Available.

Payment Protection
To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

16 Vacation rentals

Filters applied: Swimming pool

(3)

1 / 17

Holmes Beach House

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I like to call the Coral Cottage our own little Shangri La, at least for the two weeks we were pleased to be its residents. From the lovely landscaping to the private HEATED pool in the enclosed backyard, to the well equipped kitchen, just about...”
- Review left on 04/01/2016

$159

Excellent (3 reviews)

Inquire

from $159 / night

Inquire

(2)

1 / 25

Holmes Beach Townhouse

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

$225

Excellent (2 reviews)

Inquire

from $225 / night

Inquire

(1)

1 / 19

Holmes Beach Cottage

  • 3
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We couldn't have asked for a better AMI rental. I've stayed at others, but have finally found one I will stay at again (and again!) Don't worry about not being directly on the beach, because you are just a few steps away! It was wonderful to have our...”
- Review left on 04/07/2016

$271

Excellent (1 reviews)

Inquire

from $271 / night

Inquire

(1)

1 / 24

Holmes Beach Townhouse

  • 5
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Slept 13 comfortably. Great location and pool was a lifesaver with smaller children. I would highly recommend this property...”
- Review left on 07/21/2016

$300

Excellent (1 reviews)

Inquire

from $300 / night

Inquire

(21)

1 / 11

Holmes Beach Townhouse

  • 2
  • 6
  • Min stay varies
  • 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

Very Good (21 reviews)

Book

from $150 / night

Book

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 6
  • Min stay varies
  • 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

$199

Excellent (2 reviews)

Inquire

from $199 / night

Inquire
1 / 24

Holmes Beach House

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

$199

Inquire

from $199 / night

Inquire
1 / 19

Holmes Beach House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199

Inquire

from $199 / night

Inquire
1 / 24

Holmes Beach House

  • 4
  • 11
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$400

Inquire

from $400 / night

Inquire

(2)

1 / 18

Holmes Beach House

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful vacation. Absolutely loved this rental home. Everything you need is there. My family loved the pool and having beach chairs & sand toys on hand was an added bonus. Can't wait to book our next vacation in the same home...”
- Review left on 05/04/2016

$199

Excellent (2 reviews)

Inquire

from $199 / night

Inquire
1 / 34

Holmes Beach House

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

$300

Inquire

from $300 / night

Inquire

(1)

1 / 24

Holmes Beach House

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“We found this home clean and comfortable. All especially enjoyed the large open kitchen, dining, and family room areas. The very well-maintained pool and accessories were really appreciated, given red tide prohibited us from enjoying Holmes Beach...”
- Review left on 10/04/2016

$400

Very Good (1 reviews)

Inquire

from $400 / night

Inquire

(6)

1 / 16

Holmes Beach Villa

  • 3
  • 6
  • Min stay varies
  • 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

$329

Excellent (6 reviews)

Book

from $329 / night

Book

(1)

1 / 19

Holmes Beach Townhouse

  • 3
  • 6
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$199

Excellent (1 reviews)

Inquire

from $199 / night

Inquire
1 / 53

Holmes Beach House

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

$350

Inquire

from $350 / night

Inquire

(1)

1 / 47

Holmes Beach House

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“As beautiful as it looks in the photos, I actually think it's better in person. I literally want to live there. The house is so spacious, features a great open floor plan for family time, and offers 4 master bedrooms, spread out on 2 floors to...”
- Review left on 04/26/2016

$555

Excellent (1 reviews)

Inquire

from $555 / night

Inquire

Your search has been expanded 13.5 miles to include more rentals

(17)

1 / 77

Anna Maria Island Cottage - 0.1 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and I spent a week in the cottage and surrounding Anna Maria Island.We had a very relaxing vacation by the sea and enjoyed every ammentity the cottage offered.The comforts were those of our own home. Sheila was a perfect host indeed for any...”
- Review left on 08/18/2016

$186

Excellent (17 reviews)

Inquire

from $186 / night

Inquire

(1)

1 / 44

Anna Maria Island Condo - 0.1 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This was our first time renting, we usually stay at a hotel. The unit was exactly like the photos and clean as well. I had some trouble with the garbage disposal so I called the property management and they were very professional and offer to put...”
- Review left on 07/05/2016

$150

Excellent (1 reviews)

Book

from $150 / night

Book

(7)

1 / 84

Anna Maria Island Condo - 0.1 miles away

  • 2
  • 6
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Car not necessary
“Impeccable beach house! All the amenities one would want. Great Weber gas grill, (almost) private pool, brand new kitchen, brand new front loader washer/dryer (free). Cross the street and you're on the public beach, or drive 10 min north or south...”
- Review left on 11/23/2016

$250

Excellent (7 reviews)

Book

from $250 / night

Book

(1)

1 / 78

Anna Maria Island Condo - 0.1 miles away

  • 1
  • 3
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“As this was my first time to Anna Maria I was pleasantly surprised how very nice it is. My accommodations were above what I expected. The location is perfect for going to the beach, shopping, dining, or just relaxing by the pool. I enjoyed my stay so...”
- Review left on 03/10/2015

$120

Excellent (1 reviews)

Book

from $120 / night

Book
1 / 32

Anna Maria Island House - 0.1 miles away

  • 3
  • 10
  • 2 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$291

Inquire

from $291 / night

Inquire

(3)

1 / 25

Anna Maria Island Condo - 0.1 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“We had a wonderful week at the tropical sunset condo I count the days to go back with my husband and two little kids (4.5 & 1.5) We loved everything in this condo and the beach was so beautiful! We saw Manatees at the road and reel Pier and Dolphins...”
- Review left on 05/24/2016

$143

Excellent (3 reviews)

Inquire

from $143 / night

Inquire

(19)

1 / 27

Anna Maria House - 1.5 miles away

  • 4
  • 10
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool
“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

$175

Very Good (19 reviews)

Book

from $175 / night

Book

(7)

1 / 29

Anna Maria Island House - 2 miles away

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Gorgeous, beautiful home away from home. This home has everything you and your family will need. The granite kitchen is fully equipped and beautiful. I was able to make a full Thanksgiving dinner with everything that was supplied in the home! Our...”
- Review left on 11/30/2016

$400

Excellent (7 reviews)

Book

from $400 / night

Book

(68)

1 / 67

Bradenton Beach Cottage - 2 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We were suppose to go to West Palm Beach and the hurricane at that time changed our plans and we decided to look around at a place I had been to before--Anna Maria Island. We found this ad on the Sugar Shack and we were lucky it was not rented the...”
- Review left on 02/22/2017

$214

Excellent (68 reviews)

Inquire

from $214 / night

Inquire

(9)

1 / 22

Bradenton Beach Cottage - 2.2 miles away

  • 1
  • 4
  • 1 night min
  • Swimming pool
  • Ask about children
  • Air conditioning
“Good location. Clean, well supplied, good daily maid service. Not much area for being pet friendly for bathroom and for walking dog. Parking lot flooded with minimal rain. No overhang on porch at door or over chairs to get out of rain to even enjoy...”
- Review left on 08/08/2016

$155

Very Good (9 reviews)

Inquire

from $155 / night

Inquire
1 / 38

Bradenton Beach House - 2.2 miles away

  • 6
  • 16
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$500

Inquire

from $500 / night

Inquire

(2)

1 / 11

Bradenton Apartment - 2.3 miles away

  • 2
  • 4
  • 30 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Swimming pool

$74

Excellent (2 reviews)

Book

from $74 / night

Book

(1)

1 / 47

Anna Maria House - 2.3 miles away

  • 2
  • 4
  • 1 night min
  • Swimming pool
  • Air conditioning
  • Private garden

$335

Excellent (1 reviews)

Book

from $335 / night

Book

(5)

1 / 92

Anna Maria Island Condo - 2.4 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“The unit was well equipped with a good kitchen and lots of seating. TV's where great. We have two kids so we needed a place that could work for at home cooking as well. The location was perfect for us. The balcony was a perfect place for having a...”
- Review left on 01/05/2016

$250

Very Good (5 reviews)

Book

from $250 / night

Book

(2)

1 / 22

Anna Maria House - 2.4 miles away

  • 8
  • 16
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This house is simply amazing. There is nothing that could be improved upon. The house is gorgeous, clean, and very welcoming. The pool was the bomb as was the hot tub in the evenings! The best part of the pool is that it has all day sun which...”
- Review left on 04/22/2016

$599

Excellent (2 reviews)

Inquire

from $599 / night

Inquire
1 / 81

Anna Maria Island Condo - 2.4 miles away

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

$200

Book

from $200 / night

Book

(28)

1 / 97

Bradenton Beach Condo - 2.6 miles away

  • 2
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“It was a great experience. The condo was close to perfect. It was a great spot close to the beach and many restuarants and shops. The Island was perfect with free trolly service and very clean roads and ammenities. The Ocean views and the white...”
- Review left on 06/05/2016

$250

Very Good (28 reviews)

Book

from $250 / night

Book

(6)

1 / 41

Bradenton Beach Condo - 2.6 miles away

  • 2
  • 5
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning
“Mark, the owner, is very responsive in communications. He told us to just bring yourselves and everything is there, beach towel, beach chairs, towels, etc. Sure enough everything is there and in great condition. This condo complex has private...”
- Review left on 01/25/2016

$150

Excellent (6 reviews)

Inquire

from $150 / night

Inquire

(5)

1 / 93

Anna Maria Island House - 2.6 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“We enjoyed our stay at this property. The home is well decorated and all rooms are very spacious. The master bedroom is enormous with jacuzzi and large walk-in shower. The other bedrooms are very spacious too. Our manager resolved a few minor...”
- Review left on 08/10/2016

$350

Excellent (5 reviews)

Book

from $350 / night

Book

(2)

1 / 24

Bradenton Beach House - 2.8 miles away

  • 6
  • 12
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“My family and friends and I rented this property to celebrate my bachelorette weekend and we picked the most perfect house possible! The layout of the house was ideal for accommodating a large number of guests in addition to providing comfortable...”
- Review left on 09/06/2016

$400

Excellent (2 reviews)

Inquire

from $400 / night

Inquire
1 / 24

Bradenton Beach House - 2.8 miles away

  • 6
  • 14
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500

Inquire

from $500 / night

Inquire
1 / 58

Anna Maria House - 2.8 miles away

  • 4
  • 10
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$400

Inquire

from $400 / night

Inquire

(4)

1 / 60

Bradenton Villa - 3.3 miles away

  • 3
  • 6
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“We just returned from our stay in the Bayfront Villa. My husband, two teenagers and my 92-yr old Mother in law found this location to be perfect for us. My two kids thoroughly enjoyed fishing off of the dock, swimming in the pool and swimming off...”
- Review left on 06/23/2015

$213

Excellent (4 reviews)

Inquire

from $213 / night

Inquire

(1)

1 / 16

Bradenton Condo - 4.6 miles away

  • 3
  • 6
  • 90 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Ask about children
“We vacationed at this villa during February and March 2011. It is spacious and quite nicely furnished. We especially enjoyed the setting - the view from every window is of trees and shrubs with no other dwellings visible. One minor drawback of its...”
- Review left on 04/28/2011

$60

Very Good (1 reviews)

Inquire

from $60 / night

Inquire
1 / 11

Sarasota House - 4.9 miles away

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

$240

Inquire

from $240 / night

Inquire
1 / 26

Bradenton House - 5.2 miles away

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

$158

Inquire

from $158 / night

Inquire

(4)

1 / 29

Bradenton Condo - 7.2 miles away

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

$110

Excellent (4 reviews)

Book

from $110 / night

Book
1 / 23

Bradenton Villa - 7.2 miles away

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

$100

Book

from $100 / night

Book
1 / 15

Bradenton Villa - 7.3 miles away

  • 2
  • 7
  • Min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$100

Book

from $100 / night

Book

(21)

1 / 32

Palmetto House - 7.4 miles away

  • 3
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 10 mi
  • Swimming pool
“Two days after we arrived, we booked for 2018! Capt Julie and Pamela have made an enchanted, whimsical oasis where you can find a mermaid sitting on a bench in the garden, a charming metal tortoise lounging by the pool and an open, flowing old...”
- Review left on 02/20/2017

$300

Excellent (21 reviews)

Inquire

from $300 / night

Inquire
1 / 16

Bradenton House - 8.2 miles away

  • 3
  • 5
  • Min stay varies
  • Nearest beach 15 mi
  • Swimming pool
  • Child friendly

$170

Book

from $170 / night

Book

(14)

1 / 13

Longboat Key Condo - 8.3 miles away

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“Saubere, sehr gut ausgestattete und geschmackvoll eingerichtete Wohnung mit allem was man benötigt und noch vielem mehr. Im 2. Stock (= 3rd Floor in USA) gelegen, über eine Außentreppe direkt neben dem zur Wohnung gehörenden Parkplatz oder per...”
- Review left on 10/06/2016

$180

Very Good (14 reviews)

Inquire

from $180 / night

Inquire

(1)

1 / 25

Longboat Key Apartment - 9.6 miles away

  • 2
  • 4
  • 30 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning
“The condo is much larger and much more upscale then the pictures actually show. The location on the resort site makes for an excellent vacation, no noise, close to pool and fitness Center. The direction left by the owner re everything was exact and...”
- Review left on 01/04/2015

$59

Excellent (1 reviews)

Inquire

from $59 / night

Inquire

(20)

1 / 108

St. Petersburg Condo - 13 miles away

  • 2
  • 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 2 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

$135

Excellent (20 reviews)

Book

from $135 / night

Book

(6)

1 / 11

Bradenton House - 13 miles away

  • 4
  • 8
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“The house was clean and comfy. Wish that there was a central bath and the master bath was on main floor. Have bad knee and couldn't do the stairs so stayed downstairs. Pool was our sanctuary. Weather perfect. Close enough to all anemities. All in all...”
- Review left on 03/03/2017

$172

Very Good (6 reviews)

Inquire

from $172 / night

Inquire

(5)

1 / 15

Bradenton Villa - 13.1 miles away

  • 3
  • 6
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“This villa was everything you could want and more , had everything you could need down to beach chairs provided to take on the beach , it was in a peaceful surroundings overlooking a lake at the back and very comfortable inside would recommend this...”
- Review left on 09/29/2015

$133

Very Good (5 reviews)

Inquire

from $133 / night

Inquire

(11)

1 / 22

Bradenton House - 13.2 miles away

  • 4
  • 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Ask about children
“The house was lovely ~ spacious, clean, comfortable, & convenient to everything. The pool was great. Neighborhood was quiet ~ loved looking out over the lake. Great view from the living room. This was perfect for me and my family and we had...”
- Review left on 05/31/2016

$130

Very Good (11 reviews)

Inquire

from $130 / night

Inquire

(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

$100

Very Good (22 reviews)

Inquire

from $100 / night

Inquire
1 / 12

Bradenton House - 13.5 miles away

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

$236

Book

from $236 / night

Book

(5)

1 / 22

Bradenton Townhouse - 13.5 miles away

  • 2
  • 4
  • Min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning
“I enjoyed my stay in the Bradenton area. There are many good restaurants and shopping. I especially liked the owners, Mary Ann and Paul. They are so kind and very helpful. If my husband and I return to this area we could definitely want to stay...”
- Review left on 02/14/2017

$110

Very Good (5 reviews)

Inquire

from $110 / night

Inquire