The 10 best cottages in Anna Maria, US | Booking.com
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Cottages in Anna Maria

Find the cottages that appeal to you the most

The best cottages in Anna Maria

Check out our selection of great cottages in Anna Maria

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Blissful Bay at Bayside Bungalow

Anna Maria

Blissful Bay at Bayside Bungalow is located in Anna Maria, just a 13-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

M
Maderod25
From
United States
Everything was very clean and comfortable. The only bad thing was that I couldn't find where to turn on the pool lights.
Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 7 reviews
Price from
$370.25
1 night, 2 adults

Bay Breezes at Bayside Bungalow

Anna Maria

Bay Breezes at Bayside Bungalow offers accommodations in Anna Maria, a 13-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

L
Laurie
From
United States
Location was great. Right next to restaurant, pier, and within walking distance to shops.
Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 6 reviews
Price from
$654.25
1 night, 2 adults

Barefoot by the Bay at Bayside Bungalow

Anna Maria

Barefoot by the Bay at Bayside Bungalow offers accommodations in Anna Maria, a 13-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

T
Tiago
From
United States
Very clean, new and comfortable, it is just across the street to an amazing beach. Ideal to go with kids as the beach have no waves and a shallow water. Nice restaurant across the street.
Scored out of 10, guest rating 8.4
Very Good - What previous guests thought, 6 reviews
Price from
$233.56
1 night, 2 adults

Anna Maria's Finest

Anna Maria

A 5-minute walk from Anna Maria Island in Anna Maria, Anna Maria's Finest provides accommodations with access to spa facilities. This vacation home features air-conditioned accommodations with a...

B
Branden
From
United States
Place was immaculate. Very clean and plenty of space.
Scored out of 10, guest rating 8.2
Very Good - What previous guests thought, 23 reviews
Price from
$558
1 night, 2 adults

Bayside Cutie at Bayside Bungalow

Anna Maria

Bayside Cutie at Bayside Bungalow is located in Anna Maria, just a 13-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

P
Paige
From
United States
Location was perfect for our stay!
Scored out of 10, guest rating 6.2
Pleasant - What previous guests thought, 6 reviews
Price from
$613.13
1 night, 2 adults

Bradenton Escape with Private Heated Pool

Bradenton (Near Anna Maria)

Bradenton Escape with Private Heated Pool is located in Bradenton, just 14 miles from The John and Mable Ringling Museum of Art and 31 miles from Tropicana Field.

J
Johnathan
From
United States
Loved the kitchen, games for my kids to play, the outside patio!
Scored out of 10, guest rating 9.8
Exceptional - What previous guests thought, 21 reviews
Price from
$247.86
1 night, 2 adults

Bayview Pointe

Cortez (Near Anna Maria)

Bayview Pointe is located in Cortez, just a 18-minute walk from Cortez Beach and 13 miles from The John and Mable Ringling Museum of Art.

C
Charlotte
From
United States
Was very clean and in a good neighborhood. Property manager was very friendly and helpful. Amazing quick responses to our inquiries.
Scored out of 10, guest rating 9.9
Exceptional - What previous guests thought, 20 reviews
Price from
$546.98
1 night, 2 adults

Sea Gem One bed one bath charmer steps to beach

Bradenton Beach (Near Anna Maria)

Sea Gem One bed one bath charmer steps to beach is located in Bradenton Beach, just a 11-minute walk from Cortez Beach and 14 miles from The John and Mable Ringling Museum of Art.

D
Dave
From
United States
Loved the location and it was a cute cottage
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 15 reviews
Price from
$344
1 night, 2 adults

Pool home on the Bay, large private yard near AMI

Bradenton (Near Anna Maria)

Pool home on the Bay, large private yard near AMI is a recently renovated vacation home in Bradenton where guests can make the most of its outdoor swimming pool, private beach area, and garden.

K
Kirk
From
United States
Very comfortable great location.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 15 reviews
Price from
$330
1 night, 2 adults

Best Fall Rates! Heated Pool, Hot Tub, Family Fun Games, near Anna Maria Island & IMG

Bradenton (Near Anna Maria)

1.8 miles from Palma Sola Causeway Park in Bradenton, Best Fall Rates! Heated Pool, Hot Tub, Family Fun Games, near Anna Maria Island & IMG provides accommodations with access to a hot tub.

L
Layne
From
United States
Very comfortable & close to everything.
Scored out of 10, guest rating 10.0
Exceptional - What previous guests thought, 9 reviews
Price from
$311.75
1 night, 2 adults
All cottages in Anna Maria

Looking for a cottage?

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.

Most booked cottages in Anna Maria and surrounding area in the past month

See all

These cottages in Anna Maria and nearby have options with free cancellation

  • Bayview Pointe

    Cortez
    Free cancellation options available
    Scored out of 10, guest rating 9.9
    Exceptional - What previous guests thought, 20 reviews

    Bayview Pointe is located in Cortez, just a 18-minute walk from Cortez Beach and 13 miles from The John and Mable Ringling Museum of Art.

    From $912.54 per night
  • Scored out of 10, guest rating 7.7
    Good - What previous guests thought, 3 reviews

    Serendipity steps to beach & fishing dock offers accommodations in Bradenton Beach, a 11-minute walk from Cortez Beach and 14 miles from The John and Mable Ringling Museum of Art.

    From $293.85 per night
  • Scored out of 10, guest rating 1.0
    Bad - What previous guests thought, 1 review

    Reel Paradise steps to bay beach fishing dock offers accommodations in Bradenton Beach, a 11-minute walk from Cortez Beach and 14 miles from The John and Mable Ringling Museum of Art.

    From $293.85 per night
  • Bradenton Escape with Private Heated Pool

    Bradenton
    Free cancellation options available
    Scored out of 10, guest rating 9.8
    Exceptional - What previous guests thought, 21 reviews

    Bradenton Escape with Private Heated Pool is located in Bradenton, just 14 miles from The John and Mable Ringling Museum of Art and 31 miles from Tropicana Field.

    From $397.83 per night
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 9 reviews

    1.8 miles from Palma Sola Causeway Park in Bradenton, Best Fall Rates! Heated Pool, Hot Tub, Family Fun Games, near Anna Maria Island & IMG provides accommodations with access to a hot tub.

    From $793.46 per night
  • Oar House

    Anna Maria
    Free cancellation options available

    Oar House 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.

  • Kays Landing - 423

    Anna Maria
    Free cancellation options available

    Kays Landing - 423 is located in Anna Maria, just a 8-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art.

  • Shady Mango home

    Anna Maria
    Free cancellation options available
    Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Shady Mango home offers accommodations in Anna Maria, 19 miles from John and Mable Ringling Museum of Art and 19 miles from The John and Mable Ringling Museum of Art.

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

  • Scored out of 10, guest rating 8.9
    Excellent - What previous guests thought, 61 reviews

    An Island Getaway at Palm Tree Villas in Holmes Beach provides accommodations with an outdoor swimming pool, a garden, and barbecue facilities.

  • Spring Haven offers accommodations in Anna Maria, a 10-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • A 7-minute walk from Anna Maria Island in Anna Maria, Luxury Waterfront Home With A Heated Pool And Spa! features accommodations with access to a spa center.

  • Lighthouse Lagoon offers accommodations in Anna Maria, a 11-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Paradise on Pine offers accommodations in Anna Maria, a 7-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Scored out of 10, guest rating 9.7
    Exceptional - What previous guests thought, 4 reviews

    The Cottage on Pine - Luxury Boho Beach Cottage wPvt Heated Pool On Pine Ave is located in Anna Maria, just 20 miles from The John and Mable Ringling Museum of Art and a 5-minute walk from Anna Maria...

  • Jersey Gal home is located in Anna Maria, just a 9-minute walk from Anna Maria Island and 19 miles from Sarasota International Convention Center.

  • Jersey Girl home is located in Anna Maria, just a 9-minute walk from Anna Maria Island and 19 miles from Sarasota International Convention Center.

Enjoy breakfast in Anna Maria and nearby

  • Covey Cottage

    Anna Maria
    Breakfast options

    Covey Cottage is located in Anna Maria, just a 9-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Daiquiri Deck

    Anna Maria
    Breakfast options

    Daiquiri Deck offers accommodations in Anna Maria, a 9-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Island Sea-Cret

    Anna Maria
    Breakfast options
    Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 1 review

    Island Sea-Cret offers accommodations in Anna Maria, a 11-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art.

  • AMI Breeze

    Anna Maria
    Breakfast options
    Scored out of 10, guest rating 5.0
    Fair - What previous guests thought, 2 reviews

    AMI Breeze is located in Anna Maria, just a 11-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Whispering Whale Retreat is located in Anna Maria, just a 10-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • 29 Palms

    Anna Maria
    Breakfast options
    Scored out of 10, guest rating 7.0
    Good - What previous guests thought, 1 review

    29 Palms is located in Anna Maria, just a 8-minute walk from Anna Maria Island and 19 miles from The John and Mable Ringling Museum of Art. The vacation home has access to a restaurant.

  • Flip Flops and Fish Tales is located in Anna Maria, just a 10-minute walk from Anna Maria Island and 20 miles from The John and Mable Ringling Museum of Art.

  • Blue Pearl

    Anna Maria
    Breakfast options
    Scored out of 10, guest rating 7.5
    Good - What previous guests thought, 2 reviews

    Blue Pearl is located in Anna Maria, just a 8-minute walk from Anna Maria Island and 19 miles from Sarasota International Convention Center.

FAQ about cottages in Anna Maria

Cottages That Guests Love in Anna Maria

See all
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 8 reviews
    Location was quiet and nice. I love the cottage style feel of the house. Much better than the new large homes going in everywhere. The backyard had plenty of room
    Guest review by
    Chloe
    Solo traveler
  • Scored out of 10, guest rating 9.0
    Wonderful - What previous guests thought, 8 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
    Guest review by
    hazel
    Solo traveler
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review
    It had everything you could ask for in a single family vacation cottage rental.
    Guest review by
    Chloe
    Family with young children
  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 2 reviews
    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.
    Guest review by
    Shaw
    Solo traveler
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