Search Anna Maria Cottage Rentals from CA $297

  • 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
Jun 26 - Jun 28
In two months
Aug 7 - Aug 9
In three months
Sep 4 - Sep 6
In four months
Oct 2 - Oct 4

Our top choices for Anna Maria 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 CA $641
CA $1,197 total
includes taxes & fees
Jun 14 - Jun 15
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.
The price is CA $654
CA $1,615 total
includes taxes & fees
Jun 13 - Jun 14
Beautiful Guest House Near the Beach with Private Pool!
Exterior

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 CA $493
CA $1,485 total
includes taxes & fees
Jun 14 - Jun 15
Adorable Cottage with Covered Balconies and Private Pool
Property grounds

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, (26 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 CA $705
CA $1,687 total
includes taxes & fees
Jun 27 - Jun 28
Beautiful Condo on Pine Ave, 2 Blocks to Beach
Property grounds

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Palmetto
10.0 out of 10, Exceptional, (2 reviews)
"The accommodations were very comfortable and clean. Quiet neighborhood. Host was extremely helpful and pleasant. The screened porch off of the kitchen was a great place to relax with the dogs. We didn't get an opportunity to enjoy the pool and hot tub because of our other obligations but definitely will plan on staying again the next time I need to visit the area. It was like a home away from home."
United States
Douglas T.
The price is CA $139
CA $351 total
includes taxes & fees
Jul 1 - Jul 2
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (68 reviews)
"Place was great, the bed was very comfortable and we loved the new screened in porch."
United States
ken h.
The price is CA $138
CA $297 total
includes taxes & fees
Jun 26 - Jun 27
The "Grouper"
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 CA $199
CA $520 total
includes taxes & fees
Jun 9 - Jun 10
St Pete/gulfport Tiny little small home
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, (7 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 CA $153
CA $418 total
includes taxes & fees
Jun 16 - Jun 17
Coastal Luxury 7mi to Anna Maria Private Cottage
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, (22 reviews)
"Great location! "
United States
Quinton W.
The price is CA $232
CA $522 total
includes taxes & fees
Jun 15 - Jun 16
Sunny PaG Island rental w/bikes-just steps2beach
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is CA $135
CA $571 total
includes taxes & fees
Jun 21 - Jun 22
Lido Key Getaway - Bikes & Beach Gear
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, (26 reviews)
"All as promised…clean, bright…small but perfect for a couple at the beach. "
United States
reva g.
The price is CA $259
CA $557 total
includes taxes & fees
Jun 16 - Jun 17
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
1 bedroom, iron/ironing board, free WiFi, bed sheets

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
Indian Beach Sapphire Shores
9.8 out of 10, Exceptional, (39 reviews)
"Fun stay, great location"
United States
Theresa H.
The price is CA $188
CA $326 total
includes taxes & fees
Jun 22 - Jun 23
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum
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 CA $268
CA $602 total
includes taxes & fees
Jun 9 - Jun 10
Downtown Cottage | Walk Everywhere, Park once
1 bedroom, iron/ironing board, free WiFi, bed sheets

Happy Hour ACROSS THE STREET FROM THE BEACH

Happy Hour ACROSS THE STREET FROM THE BEACH
Sunshine Beach
10.0 out of 10, Exceptional, (11 reviews)
"Super accommodating, clean, and perfect location from the beach. The Happy Hour is the perfect home away from home."
United States
Morgan M.
The price is CA $213
CA $449 total
includes taxes & fees
Jun 14 - Jun 15
Happy Hour ACROSS THE STREET FROM THE BEACH
Exterior

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, (2 reviews)
"Great family resort!!"
United States
Patrick B.
The price is CA $1,734
CA $4,235 total
includes taxes & fees
Jun 9 - Jun 10
Entire Island Paradise Cottages – Heated Pool, Tiki Hut, Walk to Beach, 8 Units, Sleeps 30
Property grounds

3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is CA $3,289
CA $4,300 total
includes taxes & fees
Jun 14 - Jun 15
3716 7th Ave W
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 Hotel Reviews

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

10/10 Excellent
"We had the most amazing family vacation. The location was perfect with a short walk to the beach. They had anything you could need for the beach available from chairs, toys, paddle boards, sun shades, beach cart, cooler, beach bags and beach towels. The golf cart was such a bonus with going around the island for ice cream, shopping and dinner. We are so happy we chose to stay at this cottage."
Amy S. 7-night trip
Posted 18 hours ago
Castaway Cottage + Beach + Heated Private Pool & Spa + GOLF CART INCLUDED!

Find out more about Anna Maria

Anna Maria Cottages information

Number of reviews
426
Accommodation
27 Cottages
Lowest Price
CA $297
Highest Price
CA $4,300

Frequently asked questions

How much do cottages in Anna Maria cost?
Cottages in Anna Maria range between CA $297 and CA $4,300 per night. These stays offer a chance to reconnect with nature — at a price you can afford. These prices were 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.
What are the best cottages in Anna Maria?
There are multiple cottages in Anna Maria with a total average guest review rating of 9.7. Queen's Gate Resort is a superb place to rest and unwind between adventures. This 2.5-star cottage also features a garden and pool sun loungers. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another popular pick with travellers in this area. It has a 3-star rating and amenities including a barbecue grill and a swimming pool.
How many cottages are there in Anna Maria?
You can choose from 27 cottages in Anna Maria. No matter if you're traveling with the family or planning a retreat with close friends, Expedia will help you find the perfect property to enjoy nature's beauty.
What are the best cheap cottages in Anna Maria?
With cottages starting from just CA $297 per night, you can afford to stay a little longer in Anna Maria! One escape that's easy on the pocket is Queen's Gate Resort. Amenities here include a swimming pool and a barbecue grill. Another cost-effective pick where you can get back in touch with nature is Pool Party North - 2 Bedroom Cottage. A barbecue grill and clothes washing facilities are two of the conveniences here. If you're sightseeing in Anna Maria and want to stay within your budget, there are loads of fun and free attractions to put on your to-do list. Anna Maria Beach and Coquina Beach are favourites. 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?
Get cozy at Queen's Gate Resort, a 2.5-star cottage just a short drive from downtown. Conveniences here include a nearby beach and beach umbrellas. Another family-friendly option where you can swap the concrete jungle for wide open spaces is 105b 12th Street South Front 2 Bedroom Apts By Redawning. A barbecue grill and WiFi help make this 3-star cottage a hit with guests. Once you've checked in and unpacked your things, there are tons of family-friendly attractions to visit in and around Anna Maria. Anna Maria Beach and Coquina Beach are two popular options.
Why book your cottage in Anna Maria with Expedia?
Expedia has some great cottages in Anna Maria, so get ready for a memorable stay close to nature. If you're sticking to a budget, select how much you'd like to spend and the star rating of your property. Or, try out our filters to search for cottages with a kitchen or a pool. We'll help you find the right place whatever your trip looks like.
How can I find cheap cottages in Anna Maria?
With Expedia's helpful filter tool, getting your hands on cheap cottages in Anna Maria has never been simpler. To discover accommodations that'll make your wallet smile, narrow your search by star rating, amenities and budget.
What is there to do in Anna Maria near my cottage?
Anna Maria has enough sights and experiences to keep you entertained for weeks, starting with Anna Maria Island Museum and Historical Park. Bean Point Beach, Palmetto Avenue Beach and Island Players are other popular attractions. If you're in town a while, Bayfront Park and Historic Green Village will cap off your itinerary nicely.

Explore a world of travel with Expedia