Search Anna Maria Cottage Rentals from CA $111

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Our top choices for Anna Maria cottages

1. 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, (129 reviews)
"Has a beautiful view of the bay right behind the houseNeighbors were very friendly,has a new house being built next door but it still was quaint beach was in walking distance. Definitely a must do again."
United States
Terrence H.
The price is CA $369
CA $858 total
includes taxes & fees
Nov 15 - Nov 16
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay

2. The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (79 reviews)
"Perfect spot"
United States
Canyon L.
The price is CA $140
CA $292 total
includes taxes & fees
Nov 19 - Nov 20
The "Grouper"

3. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
9.8 out of 10, Exceptional, (14 reviews)
"Clean and nice place"
United States
Ismael
The price is CA $111
CA $349 total
includes taxes & fees
Nov 15 - Nov 16
Cozy Private Cottage, Minutes to Anna Maria Island

4. Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

Pet-friendly Bradenton Home 1.5 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 CA $248
CA $477 total
includes taxes & fees
Nov 18 - Nov 19
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach

5. Bridge Street Pier Beach House + Dog-friendly

Bridge Street Pier Beach House + Dog-friendly
Bridge Street
9.6 out of 10, Exceptional, (38 reviews)
"Great place! Perfect location to the beach and shops "
United States
Michelle R.
The price is CA $427
CA $657 total
includes taxes & fees
Nov 23 - Nov 24
Bridge Street Pier Beach House + Dog-friendly

6. Beach Getaway Near Rays, Bikes & Gear

Beach Getaway Near Rays, Bikes & Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (34 reviews)
"We love staying at this nice cozy beach house! It's so close to the beach.And such a nice quiet location!"
United States
Cathy P.
The price is CA $188
CA $461 total
includes taxes & fees
Nov 15 - Nov 16
Beach Getaway Near Rays, Bikes & Gear

7. Sunny Island Rental, Bikes, Steps2Beach

Sunny Island Rental, Bikes, Steps2Beach
Pass-a-Grille
9.4 out of 10, Exceptional, (29 reviews)
"Wonderful place to stay. Great location to the beach, restaurants and shopping. If you want a peaceful getaway highly recommend."
United States
Janise W.
The price is CA $249
CA $536 total
includes taxes & fees
Nov 22 - Nov 23
Sunny Island Rental, Bikes, Steps2Beach

8. Steps 2 Beach Cottage, King Bed, Bikes

Steps 2 Beach Cottage, King Bed, Bikes
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Excellent location, property and adorable place!"
United States
Meredith S.
The price is CA $262
CA $587 total
includes taxes & fees
Dec 6 - Dec 7
Steps 2 Beach Cottage, King Bed, Bikes

9. Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Desoto Lakes
The price is CA $133
CA $343 total
includes taxes & fees
Dec 2 - Dec 3
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.

10. 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 $203
CA $505 total
includes taxes & fees
Nov 15 - Nov 16
St Pete/gulfport Tiny little small home

11. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is CA $3,348
CA $4,378 total
includes taxes & fees
Nov 14 - Nov 15
3716 7th Ave W

12. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is CA $240
CA $688 total
includes taxes & fees
Nov 15 - Nov 16
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

13. Lido Beach Studio with Heated Pool

Lido Beach Studio with Heated Pool
Lido Key
10.0 out of 10, Exceptional, (1 review)
"Wonderful place!!"
United States
Lorraine B.
The price is CA $222
CA $549 total
includes taxes & fees
Dec 6 - Dec 7
Lido Beach Studio with Heated Pool

14. Lido Key Casita w Pool Steps to the Beach

Lido Key Casita w Pool Steps to the Beach
Lido Key
10.0 out of 10, Exceptional, (2 reviews)
"Alex was very quick to reply to my questions. Room was exactly as pictured!"
United States
Felecia P.
The price is CA $222
CA $573 total
includes taxes & fees
Nov 18 - Nov 19
Lido Key Casita w Pool Steps to the Beach

15. Downtown | Walk Everywhere, Park Once

Downtown | Walk Everywhere, Park Once
Historic Old Northeast
10.0 out of 10, Exceptional, (13 reviews)
"Nice place. Nice location."
United States
Betsy D.
The price is CA $220
CA $536 total
includes taxes & fees
Nov 16 - Nov 17
Downtown | Walk Everywhere, Park Once

16. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is CA $222
CA $573 total
includes taxes & fees
Nov 29 - Nov 30
Cozy Lido Studio by Beach & St Armand's

17. 🌅 Ocean View 2 Bedroom Cottage | Unit 6

🌅 Ocean View 2 Bedroom Cottage | Unit 6
Sunset Beach
The price is CA $367
CA $758 total
includes taxes & fees
Nov 16 - Nov 17
🌅 Ocean View 2 Bedroom Cottage | Unit 6

18. ⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7

⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7
Sunset Beach
The price is CA $424
CA $826 total
includes taxes & fees
Nov 23 - Nov 24
⭐ Sea Side 2 Bedroom 2 Bath Cottage | Unit 7

19. 🏖️ Beach Suite Collection I Pet Friendly

🏖️ Beach Suite Collection I Pet Friendly
Sunset Beach
The price is CA $480
CA $1,204 total
includes taxes & fees
Dec 2 - Dec 3
🏖️ Beach Suite Collection I Pet Friendly

20. 🌴 Beach Escape Collection | Sleeps Up to 8

🌴 Beach Escape Collection | Sleeps Up to 8
Sunset Beach
The price is CA $522
CA $1,272 total
includes taxes & fees
Nov 23 - Nov 24
🌴 Beach Escape Collection | Sleeps Up to 8
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.

Learn more about Anna Maria

This laid-back island paradise offers white-sand beaches where dolphins often swim close to shore during sunset walks. Rent a bike to explore the Pine Avenue shops, then grab fresh grouper sandwiches at Rod and Reel Pier.

A coastal town with a long pier extending into the turquoise sea, a sandy beach, and residential buildings along the shore.

Frequently Asked Questions

How much do cottages in Anna Maria cost?

Cottages in Anna Maria range between CA $111 and CA $3,348 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 9.6. 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 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 $111 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.

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