Skip to main content

The 10 Best Holiday Rentals in Anna Maria, USA

Check out our pick of great holiday rentals in Anna Maria

Filter by:


Review score

Superb: 9+ Very good: 8+ Good: 7+ Pleasant: 6+
Our top picks Lowest price first Star rating and price Top reviewed

See the latest prices and deals by choosing your dates.

Offering direct access to a terrace, the air-conditioned holiday home consists of a fully equipped kitchen and a TV. Towels and bed linen are available in the holiday home.

The nearest airport is Sarasota Bradenton International Airport, 28 km from the holiday home.

The location was amazing and the accommodations were very comfortable. The New Years gift was so sweet!

Show more Show less
9.3
Superb
6 reviews
Price from
£261
per night

The spacious holiday home features 2 bedrooms, a flat-screen TV with streaming services and a fully equipped kitchen that provides guests with a dishwasher, an oven, a washing machine, a microwave and a toaster. Featuring air conditioning, this unit has a dressing room and a fireplace. The property has an outdoor dining area.

the central location, so close to the beach, shops and restaurants. The outdoor shower was great.

Show more Show less
9.6
Exceptional
5 reviews
Price from
£316
per night

Located less than 1 km from Anna Maria Island, 32 km from The John and Mable Ringling Museum of Art and 300 metres from Anna Maria City Pier, South Bay Inn provides accommodation set in Anna Maria. Guests can access the apartment via private entrance.

The key pad entry was easy. the location was perfect. close to restaurants and shopping. Unit was clean and nice. We would rent it again.

Show more Show less
8.7
Fabulous
38 reviews
Price from
£282
per night

Boasting a DVD player, the spacious holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room, a dining area, 3 bedrooms, and 3 bathrooms with an a bath or shower. The unit is air conditioned and is comprised of a patio with outdoor furniture as well as a TV with cable channels. For added privacy, the accommodation features a private entrance.

This was a beautiful home! Loved all the windows to enjoy the outside view. Great price for such a fun little getaway! Definitely would recommend this home!!

Show more Show less
8.2
Very good
9 reviews
Price from
£557
per night

Located in Anna Maria, 300 metres from Anna Maria Island and 30 km from The John and Mable Ringling Museum of Art, Sandy's Getaway provides air-conditioned accommodation with a balcony and free WiFi. The Greens of Manatee Golf Club is within 22 km of the holiday home. The property is non-smoking and is set 1.8 km from Anna Maria City Pier.

It was clean and very comfortable. It was also in a great location.

Show more Show less
8.3
Very good
12 reviews
Price from
£326
per night

Located in Anna Maria, Sea's The Day provides accommodation with a private pool. This holiday home features accommodation with a patio. Free WiFi is available throughout the property and Anna Maria Island is 70 metres away.

perfect location for the beach and pine ave. best spot we have had and been coming over ten years

Show more Show less
8.6
Fabulous
12 reviews
Price from
£293
per night

Located in Anna Maria, Florida, this apartment offers access to an outdoor swimming pool and free WiFi. The apartment is just 850 metres from the beach.

Guests can prepare homemade meals in the full kitchen at Sunrise Garden Resort. The apartment will provide a cable TV, ironing facilities, and a balcony with garden views. The private bathroom comes with a hairdryer.

Perfect location! Easy walk to the pier, beach, restaurants and shops. It was clean, comfortable and just as cute as can be! We will stay here again without a doubt. We loved Anna Maria... So beautiful and so much to see and do!

Show more Show less
7.3
Good
193 reviews
Price from
£343
per night

With free WiFi, this 5-bedroom villa features a cable flat-screen TV, a washing machine and a fully equipped kitchen with a fridge.

The John and Mable Ringling Museum of Art is 33 km from the villa, while Anna Maria City Pier is 1.4 km from the property. The nearest airport is Sarasota Bradenton International Airport, 30 km from Bean Point Residence.

Show more Show less
10
Exceptional
1 reviews

The spacious holiday home features 4 bedrooms, a TV with satellite channels, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 4 bathrooms with a bath. For added convenience, the property can provide towels and linens for a supplement.

Show more Show less
9
Superb
1 reviews
Price from
£664
per night

Featuring a DVD player, the holiday home has a fully equipped kitchen with a dishwasher, an oven and a microwave, a living room with a seating area and a dining area, 2 bedrooms, and 1 bathroom with a walk-in shower and an a bath or shower. The unit is air conditioned and includes a patio with an outdoor dining area as well as a TV with cable channels. For added privacy, the accommodation features a private entrance.

I loved the little house, pool and closeness to the beach.

Show more Show less
5.4
Review score
5 reviews
Price from
£381
per night

Most booked holiday rentals in Anna Maria this month

Enjoy breakfast in Anna Maria!

  • Casa Posada - So Close You Can Hear the Waves Historic Beach Cottage w Beach Gear
    9.3
    Scored 9.3
    Superb
    Rated superb
     · 6 reviews

    Offering a garden and garden view, Casa Posada - So Close You Can Hear the Waves Historic Beach Cottage w Beach Gear is set in Anna Maria, 31 km from The John and Mable Ringling Museum of Art and 1.7...

  • Escape to an island adventure! Free bikes & beach items
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 5 reviews

    Set in Anna Maria in the Florida region, Escape to an island adventure! Free bikes & beach items has a patio. This property offers access to a balcony, free private parking and free WiFi.

    C'était parfait et bien situé. Tout était incroyable!

  • South Bay Inn
    Breakfast options
    8.7
    Scored 8.7
    Fabulous
    Rated fabulous
     · 38 reviews

    Located less than 1 km from Anna Maria Island, 32 km from The John and Mable Ringling Museum of Art and 300 metres from Anna Maria City Pier, South Bay Inn provides accommodation set in Anna Maria.

    Very nice, clean place and convenient to everything.

  • Coconut Tree
    Breakfast options
    8.2
    Scored 8.2
    Very good
    Rated very good
     · 9 reviews

    Situated in Anna Maria, Coconut Tree features accommodation with a private pool. Free WiFi is available throughout the property and Anna Maria Island is 300 metres away.

  • Sandy's Getaway
    Breakfast options
    8.3
    Scored 8.3
    Very good
    Rated very good
     · 12 reviews

    Located in Anna Maria, 300 metres from Anna Maria Island and 30 km from The John and Mable Ringling Museum of Art, Sandy's Getaway provides air-conditioned accommodation with a balcony and free WiFi.

    die Lage zum Strand ist super Die Einrichtung ist ok

  • Sea's The Day
    Breakfast options
    8.6
    Scored 8.6
    Fabulous
    Rated fabulous
     · 12 reviews

    Located in Anna Maria, Sea's The Day provides accommodation with a private pool. This holiday home features accommodation with a patio.

    Pool was great, beach really close, which was perfect. Beautiful island.

  • Sunrise Garden Resort
    7.3
    Scored 7.3
    Good
    Rated good
     · 195 reviews

    Located in Anna Maria, Florida, this apartment offers access to an outdoor swimming pool and free WiFi. The apartment is just 850 metres from the beach.

    Beautifully decorated and clean. Location was nice.

  • Bean Point Residence
    10.0
    Scored 10.0
    Exceptional
    Rated exceptional
     · 1 review

    Boasting air-conditioned accommodation with a private pool, garden view and a terrace, Bean Point Residence is situated in Anna Maria.

These holiday rentals in Anna Maria have options with FREE cancellation

  • Beach A La Mode - 211
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Beach A La Mode - 211 is located in Anna Maria. This property offers access to a balcony, free private parking and free WiFi.

  • Salty Sister - 302
    Free cancellation options available
    9.0
    Scored 9.0
    Superb
    Rated superb
     · 1 review

    Featuring a private pool and sea views, Salty Sister - 302 is set in Anna Maria. This beachfront property offers access to a balcony, free private parking and free WiFi.

  • The Wee Cottage
    Free cancellation options available
    5.4
    Scored 5.4
    Average
    Rated passable
     · 5 reviews

    Located in Anna Maria, The Wee Cottage provides a private pool. It is situated 32 km from The John and Mable Ringling Museum of Art and features an ATM.

  • Gulf View Estate
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Gulf View Estate is located in Anna Maria. This beachfront property offers access to a patio and free WiFi.

  • Once Upon A Time managed by Beach Retreats
    Free cancellation options available

    Boasting air-conditioned accommodation with a private pool, Once Upon A Time managed by Beach Retreats is situated in Anna Maria.

  • Gulf Shore Retreat managed by Beach Retreats

    Boasting air-conditioned accommodation with a private pool, Gulf Shore Retreat managed by Beach Retreats is situated in Anna Maria.

  • Casa Amiga managed by Beach Retreats
    Free cancellation options available

    Featuring air-conditioned accommodation with a private pool, Casa Amiga managed by Beach Retreats is set in Anna Maria. This property offers access to a balcony, free private parking and free WiFi.

  • The TipSea Turtle managed by Beach Retreats

    Featuring air-conditioned accommodation with a private pool, The TipSea Turtle managed by Beach Retreats is located in Anna Maria.

Highly rated holiday rentals in Anna Maria

FAQ about holiday rentals in Anna Maria