Search 105,200+ Vacation Rentals

Anna Maria Island Vacation Rentals & Beach Rentals with Swimming Pool - 149 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

149 Vacation rentals

Filters applied: Swimming pool

(23)

1 / 29

Anna Maria House

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

Responds fast! Avg. 1 hour 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

$225.00

Very Good (23 reviews)

Book

from $225.00 / night

1 / 24

Holmes Beach House

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

$700.00

Inquire

from $700.00 / night

(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

$250.00

Excellent (6 reviews)

Book

from $250.00 / night

(14)

1 / 26

Anna Maria Island House

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

Responds fast! Avg. 1 hour 9 minutes

“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

$200.00

Excellent (14 reviews)

Book

from $200.00 / night

(2)

1 / 20

Holmes Beach Townhouse

  • 3
  • 8
  • 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

$225.00

Excellent (2 reviews)

Inquire

from $225.00 / night

(5)

1 / 93

Anna Maria Island House

  • 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

$360.00

Excellent (5 reviews)

Book

from $360.00 / night

1 / 19

Holmes Beach Townhouse

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

$199.00

Inquire

from $199.00 / night

(9)

1 / 100

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Hidden Oasis is a lovely property - nicely decorated, very clean, very well-kept, and equipped with pretty much everything you might need or want. It also has a fantastic view of the gulf and the beach; and this view is visible from the living room...”
- Review left on 03/16/2017

$200.00

Excellent (9 reviews)

Book

from $200.00 / night

1 / 22

Anna Maria House

  • 8
  • 16
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$799.00

Inquire

from $799.00 / 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)

Inquire

from $500.00 / night

1 / 24

Holmes Beach House

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

$750.00

Inquire

from $750.00 / night

(3)

1 / 25

Anna Maria Island Condo

  • 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

$143.00

Excellent (3 reviews)

Inquire

from $143.00 / night

1 / 45

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$172.00

Book

from $172.00 / night

1 / 19

Holmes Beach House

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

$259.00

Inquire

from $259.00 / night

(5)

1 / 92

Anna Maria Island Condo

  • 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

$157.00

Very Good (5 reviews)

Book

from $157.00 / night

1 / 58

Anna Maria House

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

$499.00

Inquire

from $499.00 / night

(1)

1 / 8

Anna Maria Island Condo

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$150.00

Excellent (1 reviews)

Book

from $150.00 / night

(29)

1 / 87

Bradenton Beach Condo

  • 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

$175.00

Very Good (29 reviews)

Book

from $175.00 / night

(8)

1 / 84

Anna Maria Island Condo

  • 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

$157.00

Excellent (8 reviews)

Book

from $157.00 / night

1 / 20

Bradenton Beach Condo

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

$300.00

Book

from $300.00 / night

(1)

1 / 78

Anna Maria Island Condo

  • 1
  • 3
  • 6 nights min
  • 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

$120.00

Excellent (1 reviews)

Book

from $120.00 / night

1 / 34

Holmes Beach House

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

$715.00

Inquire

from $715.00 / night

1 / 33

Bradenton Beach House

  • 6
  • 14
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$399.00

Inquire

from $399.00 / night

1 / 26

Bradenton Beach Villa

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

Responds fast! Avg. 2 hours 59 minutes

$229.00

Book

from $229.00 / 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)

Book

from $150.00 / night

1 / 81

Anna Maria Island Condo

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

$165.00

Book

from $165.00 / night

1 / 53

Holmes Beach House

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

$449.00

Inquire

from $449.00 / night

(2)

1 / 25

Holmes Beach Townhouse

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

$259.00

Excellent (2 reviews)

Inquire

from $259.00 / night

1 / 48

Anna Maria Island House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$130.00

Book

from $130.00 / 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)

Inquire

from $599.00 / night

1 / 24

Bradenton Beach Condo

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

$200.00

Book

from $200.00 / night

1 / 18

Holmes Beach House

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

$259.00

Inquire

from $259.00 / night

(2)

1 / 47

Anna Maria House

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

Responds fast! Avg. 3 hours 23 minutes

$334.00

Excellent (2 reviews)

Book

from $334.00 / night

1 / 35

Anna Maria House

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

$186.00

Inquire

from $186.00 / night

1 / 16

Anna Maria House

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

$190.00

Inquire

from $190.00 / night

1 / 21

Holmes Beach House

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

$129.00

Inquire

from $129.00 / night

1 / 33

Holmes Beach House

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

$200.00

Inquire

from $200.00 / night

(1)

1 / 29

Anna Maria House

  • 2
  • 6
  • min stay varies
  • Swimming pool
  • Ask about children
  • Air conditioning

$215.00

Excellent (1 reviews)

Inquire

from $215.00 / night

(2)

1 / 27

Holmes Beach House

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

$165.00

Excellent (2 reviews)

Inquire

from $165.00 / night

(1)

1 / 26

Anna Maria House

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

$315.00

Excellent (1 reviews)

Inquire

from $315.00 / night