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Cottages in Anna Maria

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The 10 Best Cottages in Anna Maria, USA

Check out our selection of great cottages in Anna Maria

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Wonderful: 9+ Very Good: 8+ Good: 7+ Pleasant: 6+
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Casa Posada - So Close You Can Hear the Waves Historic Beach Cottage w Beach Gear, cottage in Anna Maria

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 km from Anna Maria City Pier. Spa facilities is available for guests. The property is non-smoking and is situated 80 metres from Anna Maria Island.

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

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9.3
Wonderful
6 reviews
Price from
$278.33
per night
Check availability
Escape to an island adventure! Free bikes & beach items, cottage in Anna Maria

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.

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9.6
Exceptional
5 reviews
Price from
$320
per night
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Coconut Tree, cottage in Anna Maria

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.

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!!

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8.2
Very Good
9 reviews
Price from
$491.33
per night
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Sandy's Getaway, cottage in Anna Maria

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.

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8.3
Very Good
12 reviews
Price from
$287.33
per night
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Sea's The Day, cottage in Anna Maria

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

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8.6
Excellent
12 reviews
Price from
$265
per night
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Sunrise Garden Resort, cottage in Anna Maria

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!

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7.3
Good
195 reviews
Price from
$278
per night
Check availability
Canal Front with Dock, 9 beds, 8,5 baths on Anna Maria Island!, cottage in Anna Maria

Situated in Anna Maria, 300 metres from Anna Maria Island and 30 km from The John and Mable Ringling Museum of Art, Canal Front with Dock, 9 beds, 8,5 baths on Anna Maria Island! offers an outdoor swimming pool and air conditioning. A hot tub is available for guests. There is a sun terrace and guests can make use of free WiFi and free private parking.

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Price from
$2,152.50
per night
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From Dusk 'Til Dune, Gorgeous 5 beds, 5,5 Baths Home on the Canal and steps away from the beach!, cottage in Anna Maria

Set in Anna Maria, 200 metres from Anna Maria Island and 31 km from The John and Mable Ringling Museum of Art, From Dusk 'Til Dune, Gorgeous 5 beds, 5,5 Baths Home on the Canal and steps away from the beach! offers a private beach area and air conditioning. This holiday home is less than 1 km from Anna Maria City Pier. The holiday home features an outdoor swimming pool with a pool bar, as well as a hot tub and a lift.

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Compass Rose, 9 bed, 8,5 bath with amazing views!, cottage in Anna Maria

Set in Anna Maria, 200 metres from Anna Maria Island and 30 km from The John and Mable Ringling Museum of Art, Compass Rose, 9 bed, 8,5 bath with amazing views! offers air conditioning. This holiday home is 1.3 km from Anna Maria City Pier. The holiday home features an outdoor swimming pool with a pool bar, along with hot tub and free WiFi.

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Anna Maria Beach House, 5 beds 6,5 baths, roof-top deck and pet-friendly!, cottage in Anna Maria

Boasting air-conditioned accommodation with a private pool, Anna Maria Beach House, 5 beds 6,5 baths, roof-top deck and pet-friendly! is set in Anna Maria. The property is around 300 metres from Anna Maria Island, 30 km from The John and Mable Ringling Museum of Art and less than 1 km from Anna Maria City Pier. In addition to free WiFi, the property also offers a sun terrace as well as a hot tub.

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Price from
$1,353
per night
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All cottages in Anna Maria

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Cottages are perfect for travelers who enjoy feeling cozy and independent in the countryside. Usually small, traditionally built houses, cottages are spread across one or two floors – making them great for families or vacations with a little more privacy.
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Most booked cottages 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
    Wonderful
    Rated wonderful
     · 6 reviews

    A few steps from Anna Maria Island in Anna Maria, Casa Posada - So Close You Can Hear the Waves Historic Beach Cottage w Beach Gear features accommodations with access to spa facilities.

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

    Just a 5-minute walk from Anna Maria Island and 700 yards from Anna Maria City Pier, Escape to an island adventure! Free bikes & beach items features accommodations in Anna Maria with a terrace.

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

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

    Coconut Tree offers accommodations in Anna Maria, 19 miles from The John and Mable Ringling Museum of Art and 1.1 miles from Anna Maria City Pier.

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

    Sandy's Getaway is located in Anna Maria, just a 3-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art.

    die Lage zum Strand ist super Die Einrichtung ist ok

  • Sea's The Day
    Breakfast options
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 12 reviews

    Sea's The Day is located in Anna Maria, just 20 miles from The John and Mable Ringling Museum of Art and a 14-minute walk from Anna Maria City Pier. Guests can go for a swim in the private pool.

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

  • Canal Front with Dock, 9 beds, 8,5 baths on Anna Maria Island!

    Canal Front with Dock, 9 beds, 8,5 baths on Anna Maria Island! is located in Anna Maria, just a 3-minute walk from Anna Maria Island and 18 miles from The John and Mable Ringling Museum of Art.

  • From Dusk 'Til Dune, Gorgeous 5 beds, 5,5 Baths Home on the Canal and steps away from the beach!

    From Dusk 'Til Dune, Gorgeous 5 beds, 5,5 Baths Home on the Canal and steps away from the beach!

  • Compass Rose, 9 bed, 8,5 bath with amazing views!

    Compass Rose, 9 bed, 8,5 bath with amazing views! offers accommodations in Anna Maria, 19 miles from The John and Mable Ringling Museum of Art and a 15-minute walk from Anna Maria City Pier.

These cottages in Anna Maria have options with FREE cancellation

  • Anna Maria Beach House, 5 beds 6,5 baths, roof-top deck and pet-friendly!

    Offering an outdoor swimming pool, Anna Maria Beach House, 5 beds 6,5 baths, roof-top deck and pet-friendly! provides accommodations in Anna Maria.

  • Surrounded By Sea Breezes - Anna Maria, FL
    Free cancellation options available

    Just a 5-minute walk from Anna Maria Island and 1.1 miles from Anna Maria City Pier, Surrounded By Sea Breezes - Anna Maria, FL features accommodations in Anna Maria with a garden.

  • Tropical Gulf View Estate - Anna Maria, FL
    Free cancellation options available

    Just a 16-minute walk from Anna Maria Island and 400 yards from Anna Maria City Pier, Tropical Gulf View Estate - Anna Maria, FL features accommodations in Anna Maria, with an outdoor swimming pool...

  • Bodacious Oasis, three bedrooms and two and half bathrooms plus den in Anna Maria

    Just a 12-minute walk from Anna Maria Island and 400 yards from Anna Maria City Pier, Bodacious Oasis, three bedrooms and two and half bathrooms plus den in Anna Maria features accommodations in Anna...

  • Dolphins Run home
    Free cancellation options available

    Dolphins Run home offers accommodations in Anna Maria, a 8-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • 29 Palms
    Free cancellation options available

    29 Palms offers accommodations in Anna Maria, 19 miles from The John and Mable Ringling Museum of Art and a 5-minute walk from Anna Maria City Pier.

  • The Bea's Knees home
    Free cancellation options available

    The Bea's Knees home offers accommodations in Anna Maria, a 5-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art.

  • Luxe Island Escape
    Free cancellation options available

    Luxe Island Escape is located in Anna Maria, just a 6-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

Traveling by car? These cottages in Anna Maria offer free parking!

FAQ about cottages in Anna Maria

Cottages That Guests Love in Anna Maria

  • Sundance Cottage

    Sundance Cottage

    Cottage in Anna Maria
    9.7
    Scored 9.7
    Exceptional
    Rated exceptional
     · 3 reviews
    Space was really cute. The bed in the second bedroom was VERY uncomfortable. Lots of cabinets in the kitchen but very disorganized. Loved the covered porches and grill. Pool was nice. Beach access was really close. Shutters and windows were great for letting in natural light, Would stay there again!! Looking forward to the North Shore of AMI again.Great
    hazel
    Solo traveler
  • Bean Point Residence

    Bean Point Residence

    Cottage in Anna Maria
    10
    Scored 10
    Exceptional
    Rated exceptional
     · 1 review
    Beautiful home. Two separate units, both self contained but as there was 7 of us we used both the upstairs and downstairs units. Beautifully appointed, airy, large accommodation. The beach is literally minutes walk away and is stunning. Pool/garden has a salt water pool & hot tub, lovely relaxing area. This home is airy and light and the furnishings appear new. Hope to return soon.
    Vicky
    Family with young children
  • Sunrise Garden Resort

    Sunrise Garden Resort

    Cottage in Anna Maria
    Avg. price/night: $470.95
    7.3
    Scored 7.3
    Good
    Rated good
     · 195 reviews
    The bed was so comfortable! Very good location, easy access to beach, restaurants, shops on foot. Lovely little bungalow type room right next to the pool & easy parking. Free washing machines and dryers too! Big bathroom & well equipped kitchen. Nice and quiet too.
    cferrant
    Family with young children
  • Shady Mango home

    Shady Mango home

    Cottage in Anna Maria
    10
    Scored 10
    Exceptional
    Rated exceptional
     · 1 review
    It had everything you could ask for in a single family vacation cottage rental.
    Chloe
    Family with young children
  • Coconut Lagoon - Lovely Historic Renovated Cottage wHuge Heated Pool Backyard OasisCabanaBar

    Coconut Lagoon - Lovely Historic Renovated Cottage wHuge Heated Pool Backyard OasisCabanaBar

    Cottage in Anna Maria
    10
    Scored 10
    Exceptional
    Rated exceptional
     · 1 review
    Location was perfect- walkable to both the beach and the bay and shops. The cottage is adorable and provided all we needed and we appreciated and used the owner's notebook with restaurant and activity suggestions. The back yard and pool area was a godsend as it was too cold and windy to be on the beach.
    Shaw
    Solo traveler
  • Escape to an island adventure! Free bikes & beach items

    Escape to an island adventure! Free bikes & beach items

    Cottage in Anna Maria
    9.6
    Scored 9.6
    Exceptional
    Rated exceptional
     · 5 reviews
    Perfect beach home, charming, cosy and quaint. Generously equipped with an unbeatable location - beaches at both ends of the street and one street over from the restaurants and shops! Felt a million miles away from the soulless orlando housing estates. Just beautiful, don't hesitate - book!
    william
    Solo traveler
  • Sunrise Garden Resort

    Sunrise Garden Resort

    Cottage in Anna Maria
    Avg. price/night: $470.95
    7.3
    Scored 7.3
    Good
    Rated good
     · 195 reviews
    quaint cottages, clean, great location
    Holly
    Young couple
  • Sunrise Garden Resort

    Sunrise Garden Resort

    Cottage in Anna Maria
    Avg. price/night: $470.95
    7.3
    Scored 7.3
    Good
    Rated good
     · 195 reviews
    great location. cute cottages. nice pool. outlet for charging my Tesla 120v
    Ronald
    Young couple
  • Sea's The Day

    Sea's The Day

    Cottage in Anna Maria
    8.6
    Scored 8.6
    Excellent
    Rated excellent
     · 12 reviews
    Adorable Bungalow steps from the beach and local eateries. No need to drive if you don’t want to.
    Kim
    Family with young children
  • The Seashell Cottage

    The Seashell Cottage

    Cottage in Anna Maria
    8.4
    Scored 8.4
    Very Good
    Rated very good
     · 14 reviews
    The cottage was very clean. Loved the sense of humor of the vacasa employee I messaged with. Very near the beach. The backyard was quite private and fully fenced so our pooch was happy. A/C worked very well. We felt very safe.
    Myrna
    Young couple

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