Search Cottages in Anna Maria Island

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Feb - 22 Feb
In two months
3 Apr - 5 Apr
In three months
1 May - 3 May
In four months
29 May - 31 May

Our top choices for Anna Maria Island cottages

Exterior

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.6 out of 10, Exceptional, (41 reviews)
"The house was fantastic, clean and a great location. It had Everything and more than you needed. Will definitely return for a longer trip x"
United Kingdom
Danielle E.
Adorable Cottage with Covered Balconies and Private Pool
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, (122 reviews)
"Great location"
United States
Steve H.
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, (32 reviews)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
Beautiful Guest House Near the Beach with Private Pool!
Exterior

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Anna Maria
10.0 out of 10, Exceptional, (1 review)
"Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at...
United States
Devon F.
The price is €1,909
includes taxes & fees
6 Mar - 7 Mar
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Exterior

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
10.0 out of 10, Exceptional, (1 review)
"Perfect vacation get away. Host are very good to work with. Everything was exactly as we wanted it! "
United States
Kara F.
The price is €356
includes taxes & fees
5 Mar - 6 Mar
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (194 reviews)
"Very charming place! Great location for the beach and restaurants. Would definitely stay again."
United States
Blaine
The price is €383
includes taxes & fees
10 Feb - 11 Feb
The Inn On Siesta Key
Property grounds

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
10.0 out of 10, Exceptional, (3 reviews)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
7mi to Anna Maria Newly Renovated Private Cottage
Interior

Family Fun: Ping Pong, Bbq, Walk to Park Nearby

Family Fun: Ping Pong, Bbq, Walk to Park Nearby
3.0 star property
Fruitville
Family Fun: Ping Pong, Bbq, Walk to Park Nearby
House (3 Bedrooms) | Interior

3 Mi to Downtown Bradenton: Family Home w/ Yard!

3 Mi to Downtown Bradenton: Family Home w/ Yard!
3.0 star property
Bradenton
The price is €401
includes taxes & fees
8 Feb - 9 Feb
3 Mi to Downtown Bradenton: Family Home w/ Yard!
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (45 reviews)
"We really enjoyed our stay here. So close to AMI "
United States
Taylor B.
The price is €185
includes taxes & fees
8 Feb - 9 Feb
The "Grouper"
Exterior

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

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (20 reviews)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
The price is €312
includes taxes & fees
10 Feb - 11 Feb
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Exterior

St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
10.0 out of 10, Exceptional, (3 reviews)
"The house was decorated nicely, it was clean, and inside/outside was well kept. The hosts were lovely and responded quickly to questions with precise information. If I need a place to stay in Gulfport again, I would not hesitate to stay!"
United States
Karen J.
The price is €354
includes taxes & fees
1 Mar - 2 Mar
St Pete/gulfport Tiny little small home
Exterior

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.

1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
Bayou Oaks
The price is €85
includes taxes & fees
6 Feb - 7 Feb
1-bedroom cottage in a park like setting! Close to Spring Training and Beaches.
Property grounds

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (18 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is €288
includes taxes & fees
10 Feb - 11 Feb
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Sarasota
9.2 out of 10, Wonderful, (178 reviews)
"Wonderful property with an excellent location! Beach access was across the street and the trolley pick-up was at the end of the block. The village was within walking distance as well. The property was very clean and the beds were comfortable. The washer and dryer is located right outside of the unit and beach chairs and a cooler were provided. We look forward to booking this property again in the future! "
United States
Alison B.
The price is €427
includes taxes & fees
9 Feb - 10 Feb
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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.
The price is €686
includes taxes & fees
6 Feb - 7 Feb
Yellow Palm Cottage steps from the beach
Property grounds

Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (6 reviews)
"The location is great. in a few minutes you are in North Shore Park walking along Tampa Bay. The cottage was clean and cozy. We just might rent it again next time we visit family in the area."
United States
Cynthia S.
The price is €389
includes taxes & fees
9 Feb - 10 Feb
Downtown Cottage | Walk Everywhere, Park once
Interior

Stylish Retro Vibes Private BBQ & Beach Access

Stylish Retro Vibes Private BBQ & Beach Access
3.0 star property
Sarasota
Stylish Retro Vibes Private BBQ & Beach Access
Exterior

Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is €805
includes taxes & fees
24 Feb - 25 Feb
Blue Dolphin Cottage steps from the beach
Exterior

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

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.8 out of 10, Exceptional, (44 reviews)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
United States
James C.
The price is €508
includes taxes & fees
1 Mar - 2 Mar
Steps 2 Beach- Cottage w/king bd +2bikes +parking
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

10/10 Excellent
"Very clean room. Helpful staff. "
Marcene 7-night trip
Posted 3 days ago
Bali Hai Beachfront Resort and Spa

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
570
Accommodation
61 Cottages
Lowest Price
€185
Highest Price
€1,909

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 9.6, 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 favoured by travellers. 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 €185 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 cosy charm of a cottage is perfect for holidaying 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 traveller 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 accommodation that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

Explore a world of travel with Expedia