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

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sep - 27 Sep
In four months
23 Oct - 25 Oct

Our top choices for Anna Maria Island cottages

Property grounds

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 AED 1,451
AED 2,829 total
includes taxes & fees
9 Jul - 10 Jul
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Exterior

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.
Beautiful Guest House Near the Beach with Private Pool!
Balcony view

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 AED 1,111
AED 1,459 total
includes taxes & fees
12 Jul - 13 Jul
The Inn On Siesta Key
Property grounds

Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (10 reviews)
"Place was clean, cozy and cute! Host communication was friendly, clear and concise. Would absolutely recommend!"
United States
Tracee Candace L.
Coastal Luxury 7mi to Anna Maria Private Cottage
Exterior

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 AED 364
AED 775 total
includes taxes & fees
30 Jul - 31 Jul
The "Grouper"
Exterior

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
House (2 Bedrooms) | Interior

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 AED 643
AED 1,234 total
includes taxes & fees
6 Jul - 7 Jul
Pet-friendly Bradenton Home ~ 3 Mi to Cortez Beach
Exterior

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 AED 526
AED 1,363 total
includes taxes & fees
7 Jul - 8 Jul
St Pete/gulfport Tiny little small home
Property grounds

Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
Pink Mango Cottage steps from the beach
Property grounds

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)
"Great location! "
United States
Quinton W.
The price is AED 588
AED 1,339 total
includes taxes & fees
9 Jul - 10 Jul
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

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 AED 724
AED 1,591 total
includes taxes & fees
18 Jul - 19 Jul
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Outdoor dining

Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is AED 485
AED 1,436 total
includes taxes & fees
5 Aug - 6 Aug
Cozy Lido Key Studio Steps to Beach & Kayaking
Exterior

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
South Village
9.6 out of 10, Exceptional, (89 reviews)
"Great location and very clean. The host was responsive and easy to communicate with throughout our stay. The property had everything we needed and more, and all amenities were well-maintained. Would definitely stay here again."
United States
Jaiden W.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Exterior

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.
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Outdoor dining

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
9.6 out of 10, Exceptional, (8 reviews)
"The most well maintained property I've ever stayed."
United States
Russ H.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Property grounds

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 AED 705
AED 1,580 total
includes taxes & fees
3 Aug - 4 Aug
Downtown Cottage | Walk Everywhere, Park once
House (4 Bedrooms) | Interior

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 AED 657
AED 2,241 total
includes taxes & fees
15 Jul - 16 Jul
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool
Property grounds

Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool
Siesta Key
9.8 out of 10, Exceptional, (7 reviews)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
The price is AED 1,265
AED 2,542 total
includes taxes & fees
12 Jul - 13 Jul
Haven cottage Across street from beach and Heated Pool
Dining

Entire Island Paradise Cottages – Heated Pool, Tiki Hut, Walk to Beach, 8 Units, Sleeps 30

Entire Island Paradise Cottages – Heated Pool, Tiki Hut, Walk to Beach, 8 Units, Sleeps 30
Madeira Beach
10.0 out of 10, Exceptional, (3 reviews)
"Great family resort!!"
United States
Patrick B.
Entire Island Paradise Cottages – Heated Pool, Tiki Hut, Walk to Beach, 8 Units, Sleeps 30
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.
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Top Anna Maria Island Hotel Reviews

Tropic Isle at Anna Maria Island Inn

Tropic Isle at Anna Maria Island Inn

10/10 Excellent
"From what we could see, the Tropic Isle rooms were very nice. However, our room had some maintenance / construction work done the day prior, and the staff thought it was too dusty for anyone to stay, so they upgraded us to a REALLY nice room on the Sea Breeze property. The room was beautiful, very clean, with a comfortable bed and a very large flat screen TV. Best of all, our window had a panoramic view of the ocean. Step off the back patio, and you were literally on the beach. The view from our room was almost surreal. Thanks so much to the staff for such a spectacular upgrade, with no need for us to complain about the first room. They took the initiative and went the extra mile for us. Very much appreciated!"
Thomas 1-night trip
Posted 2 hours ago
Tropic Isle at Anna Maria Island Inn

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.
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.