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Check prices for these dates

In two weeks
Jun 12 - Jun 14
In two months
Jul 24 - Jul 26
In three months
Aug 21 - Aug 23
In four months
Sep 18 - Sep 20

Our top choices for Anna Maria Island cottages

Property grounds

Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach
Bradenton Beach
8.6 out of 10, Excellent, (4 reviews)
"It was nice to be so close to the beach, and walking distance to places to eat. I enjoyed driving around the island and seeing the little villages. The cottage was comfortable and had many conveniences. "
United States
Valerie T.
The price is ￥27,857
￥92,164 total
includes taxes & fees
May 26 - May 27
Romantic Island Getaway! Just Steps from the Beach
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, (125 reviews)
"Was very enjoyable! Great place for our family to stay and visit!"
United States
john V.
The price is ￥47,595
￥102,961 total
includes taxes & fees
May 26 - May 27
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)
"Everything was fantastic!"
United States
Kevin O.
The price is ￥87,390
￥199,122 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 ￥83,092
￥207,044 total
includes taxes & fees
Jun 14 - Jun 15
Adorable Cottage with Covered Balconies and 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 ￥58,462
￥74,876 total
includes taxes & fees
May 30 - May 31
The Inn On Siesta Key
Exterior

The "Grouper"

The "Grouper"
Sunny Shores
9.4 out of 10, Exceptional, (66 reviews)
"Perfect location to Anna Maria Island-real “old Florida” feel."
United States
Mary W.
The price is ￥15,759
￥33,742 total
includes taxes & fees
May 28 - May 29
The "Grouper"
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 ￥12,894
￥41,892 total
includes taxes & fees
May 26 - May 27
Coastal Luxury 7mi to Anna Maria Private Cottage
Outdoor dining

Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Tropical Treehouse · 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.
The price is ￥26,106
￥58,260 total
includes taxes & fees
Jun 10 - Jun 11
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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 ￥17,510
￥79,178 total
includes taxes & fees
May 31 - Jun 1
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
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 ￥13,244
￥36,136 total
includes taxes & fees
May 27 - May 28
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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, (25 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 ￥28,321
￥61,394 total
includes taxes & fees
May 26 - May 27
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
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, (20 reviews)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is ￥25,469
￥57,853 total
includes taxes & fees
May 29 - May 30
Sunny PaG Island rental w/bikes-just steps2beach
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 ￥22,779
￥58,771 total
includes taxes & fees
May 29 - May 30
St Pete/gulfport Tiny little small home
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, (87 reviews)
"Great stay - flexible early check-in!"
United States
Jill P.
The price is ￥15,759
￥47,925 total
includes taxes & fees
Jun 10 - Jun 11
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Beach nearby

New Listing Sunset Tropical Beach Bungallow

New Listing Sunset Tropical Beach Bungallow
Sunset Beach
9.8 out of 10, Exceptional, (39 reviews)
"Great location! We'll definitely book again!"
United States
Carolyn J.
The price is ￥24,235
￥59,380 total
includes taxes & fees
May 28 - May 29
New Listing Sunset Tropical Beach Bungallow
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
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, (48 reviews)
"Yes, the Host went over the top very clean very accommodating great location!!!"
United States
Susan T.
The price is ￥39,731
￥79,491 total
includes taxes & fees
Jun 9 - Jun 10
Steps 2 Beach- Cottage w/king bd +2bikes +parking
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, (182 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is ￥53,962
￥90,521 total
includes taxes & fees
Jun 15 - Jun 16
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
House (3 Bedrooms) | Interior

Unwind Poolside + Walk to Beach! Sarasota Retreat

Unwind Poolside + Walk to Beach! Sarasota Retreat
3.0 star property
South Village
8.0 out of 10, Very Good, (1 review)
"The location of the property was excellent. The home was clean and had everything we needed to prepare breakfast in the morning. The 3 bedrooms and 3 bathrooms made it easy for the six of us wash up and get ready for dinner after a fun fill day at the walkable beach. Beach was great. Having a pool at the property was great for the 2 youngsters. We also made use of the wagon that was available to carry items to the beach., The property is nothing fancy but a great value for the money. "
United States
Eleuterio
The price is ￥29,130
￥85,707 total
includes taxes & fees
Jun 11 - Jun 12
Unwind Poolside + Walk to Beach! Sarasota Retreat
Property grounds

Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (8 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 ￥30,563
￥68,016 total
includes taxes & fees
May 26 - May 27
Downtown Cottage | Walk Everywhere, Park once
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

4/10 Poor
"Bad experience- came back to the room from dinner in the evening and key/ wristband wouldn’t work, Went to the front desk 3 times, new bands were given to us but still couldn’t get into our room, We stood outside the room for almost 2 hours before maintenance could get us in. Front desk didn’t apologize once and were very nonchalant about the entire situation. We then had to pack up and move to another room, by this time it was almost midnight. And to top it off, we pulled down the sheets to go to bed and a baby roach ran across the bed. When I spoke to the manager the next morning, she never apologized and didn’t flinch at all when I told her about the roach in the sheets. They gave me a small discount on one night, which I felt was really pathetic. Poor customer service, I will NOT be returning."
Stephanie 2-night trip
Posted 8 hours ago
Tropic Isle at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
871
Accommodation
53 Cottages
Lowest Price
￥33,742
Highest Price
￥207,044

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 9.5, 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 ￥33,742 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.

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