An aerial view of a coastal town with a long pier extending into turquoise waters.

Search Anna Maria Island Cottage Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Anna Maria Island cottages

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Anna Maria
9.6 out of 10, Exceptional, (126 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is ¥63,414
¥124,169 total
includes taxes & fees
Jul 6 - Jul 7
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.8 out of 10, Excellent, (37 reviews)
"House was in great condition and very comfortable. Ideal location! "
United States
Scott B.
The price is ¥75,446
¥183,208 total
includes taxes & fees
Jul 17 - Jul 18
Beautiful Guest House Near the Beach with Private Pool!

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (47 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is ¥68,780
¥176,777 total
includes taxes & fees
Jul 14 - Jul 15
Adorable Cottage with Covered Balconies and Private Pool

Beautiful Condo on Pine Ave, 2 Blocks to Beach

Beautiful Condo on Pine Ave, 2 Blocks to Beach
Anna Maria
8.8 out of 10, Excellent, (27 reviews)
"Nice place, a little noisy in the morning but a good convenient location for a girls trip. It was clean and beds were decent. The water pressure was not great but that being said, I would stay here again!"
United States
Amy H.
The price is ¥100,812
¥222,398 total
includes taxes & fees
Jul 3 - Jul 4
Beautiful Condo on Pine Ave, 2 Blocks to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach
Anna Maria
10.0 out of 10, Exceptional, (3 reviews)
"This was our family’s first time visiting AMI and we will definitely be back. The location of the property was awesome - its steps from the beach. It’s less than a mile to walk to restaurants and shops, but we loved having a golf cart that made it easy to go out for dinners and get groceries from the Publix. I was a little nervous with what I read about the Bean Point beach because of the currents, but my 4, 6, and 8 year olds were totally fine in the water. The beach was clean and is great for...
United States
Tierney L.
The price is ¥127,641
¥222,209 total
includes taxes & fees
Jul 15 - Jul 16
Sea Glass Cottage North End Of Anna Maria• 2bed/2 bath w/ pool Steps to Beach

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (71 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is ¥16,031
¥34,486 total
includes taxes & fees
Jul 19 - Jul 20
The "Grouper"

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (199 reviews)
"This property was everything we wanted...although not on the beach, it was a short walk to the beach and chairs, umbrellas, coolers and wagons were provided to the beach. The pool area was very comfortable and clean. We like that there were only 6 units...each was unique and very clean. We stayed in "The Nook" which was perfect for our getaway."
United States
Michele
The price is ¥64,938
¥82,383 total
includes taxes & fees
Jul 2 - Jul 3
The Inn On Siesta Key

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (9 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
The price is ¥11,561
¥40,649 total
includes taxes & fees
Jul 5 - Jul 6
Coastal Luxury 7mi to Anna Maria Private Cottage

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
3.0 star property
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"Very nice place to stay. Clean and a lot of amenities. We enjoyed all the little touches that went into decorating the house, giving it a beach house feel. We would definitely stay here again. "
United States
Rob
The price is ¥28,455
¥54,630 total
includes taxes & fees
Jul 2 - Jul 3
Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach

St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
10.0 out of 10, Exceptional, (4 reviews)
"Really nice place to stay and host communication was excellent "
United States
Susan D.
The price is ¥23,268
¥60,521 total
includes taxes & fees
Jul 8 - Jul 9
St Pete/gulfport Tiny little small home

Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
"This place was so cute and quaint! It was just a short walk to the village and to the beach. The grounds were beautiful! A little oasis in the backyard. . Would stay here again!!!"
United States
Tami B.
Yellow Palm Cottage steps from the beach

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.2 out of 10, Wonderful, (23 reviews)
The price is ¥27,681
¥60,977 total
includes taxes & fees
Jul 19 - Jul 20
Sunny PaG Island rental w/bikes-just steps2beach

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is ¥16,031
¥56,452 total
includes taxes & fees
Jul 8 - Jul 9
Cozy Lido Key Studio Steps to Beach & Kayaking

Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (49 reviews)
"Yes, the Host went over the top very clean very accommodating great location!!!"
United States
Susan T.
The price is ¥33,717
¥72,626 total
includes taxes & fees
Jul 18 - Jul 19
Steps 2 Beach- Cottage w/king bd +2bikes +parking

Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is ¥16,031
¥56,452 total
includes taxes & fees
Jul 2 - Jul 3
Cozy Lido Key Bungalow by Pool & Beach

Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
Sunny Lido Studio - Modern Touches

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
10.0 out of 10, Exceptional, (27 reviews)
"All as promised…clean, bright…small but perfect for a couple at the beach. "
United States
reva g.
The price is ¥33,092
¥67,905 total
includes taxes & fees
Jul 18 - Jul 19
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (9 reviews)
"The accommodations were great! The host communicated really well and we enjoyed walking everywhere! Highly recommend this quaint location. "
United States
Amy C.
The price is ¥39,336
¥80,113 total
includes taxes & fees
Jul 30 - Jul 31
Downtown Cottage | Walk Everywhere, Park once

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard

4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
3.0 star property
St. Petersburg
The price is ¥29,105
¥99,194 total
includes taxes & fees
Jul 2 - Jul 3
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Anna Maria Island Hotel Reviews

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
627
Accommodation
57 Cottages
Lowest Price
¥34,486
Highest Price
¥222,398

Frequently asked questions

What are the best cottages in Anna Maria Island?
There are multiple cottages in Anna Maria Island with a total average guest review rating of 9.7, so you're sure to snag a place that suits your style. Planning to stay in Bradenton Beach? Queen's Gate Resort is one property favored by travelers. This 2.5-star cottage includes amenities such as a swimming pool and a garden. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated escape where you'll be close to nature. A barbecue grill and a swimming pool are two of the conveniences waiting for you at this 3-star pick in Bradenton Beach.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only ¥34,486 per night, you can afford an extra couple of nights in Anna Maria Island for outdoor fun. If Bradenton Beach is on your travel radar, book a room at Queen's Gate Resort. A garden and a swimming pool help make this option an excellent choice. You'll also find inexpensive cottages in Holmes Beach. Take deep, calming breaths in nature during your stay at Queen's Gate Resort and take advantage of conveniences like pool sun loungers and a garden. If you're exploring Anna Maria Island and want to save money, there are many fabulous free attractions to put on your itinerary. Anna Maria Beach and Coquina Beach are always popular with visitors. This price was available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
Are there any family-friendly cottages in Anna Maria Island?
There are indeed. Whether it's in one of Anna Maria Island's busy cities or way out in nature, the cozy charm of a cottage is perfect for vacationing families. If Bradenton Beach is on your radar, book a stay at Queen's Gate Resort. This 2.5-star option offers a nearby beach and a barbecue grill. Another superb choice is 105b 12th Street South Front 2 Bedroom Apts By Redawning. Also in Bradenton Beach, this family-friendly cottage has a 3-star rating and includes WiFi and a barbecue grill. You'll find plenty of awesome things to do with the family in Bradenton Beach. Anna Maria Beach and Coquina Beach promise a fantastic day out.
Why book your cottage in Anna Maria Island with Expedia?
Reserving a cottage in Anna Maria Island is as simple as entering your travel dates and choosing an ideal place for a getaway in nature. From ritzy retreats to affordable properties and cottages that feature amenities like a kitchenette, Expedia has something for all traveler styles. As for the best offers around? We've got them as well!
How can I find cheap cottages in Anna Maria Island?
With Expedia's helpful filter tool, sourcing cheap cottages in Anna Maria Island has never been simpler. To discover accommodations that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

Explore a world of travel with Expedia