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Cottages in Anna Maria Island

Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9

2.0 star property
8.0 out of 10, Very Good, (1)
"We have stayed at this property at least 20 times before but always booked through the hotel. The property and location are terrific for what we want from Anna Maria Island. However booking through this agency was more expensive and while it worked out OK, the idea that at this price you can only have one trash bag, two roles of toilet paper, and two dishwasher pods seems a bit extreme and showed a lack of good will we thought."
The price is ¥25,375
¥73,619 total
includes taxes & fees
Jul 6 - Jul 7
Charming Anna Maria Island condo close to Bridge Street - Tradewinds #9

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

9.6 out of 10, Exceptional, (75)
"We loved everything about this rental! There are so many fun restaurants and bars within walking distance! There's also the convenience of the trolley stop right across the street for trips into the Village. The pool was nice and the beach was very close. We'd definitely recommend this location and we hope to be back next year!"
The price is ¥14,355
¥43,365 total
includes taxes & fees
Jul 6 - Jul 7
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

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

10.0 out of 10, Exceptional, (4)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
The price is ¥18,125
¥44,080 total
includes taxes & fees
Jun 22 - Jun 23
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Pool Beach Supplies Outdoor Shower PingPong Table

10.0 out of 10, Exceptional, (7)
"This was a super cute house, the property was just as great. Everything was super clean and nice. We had a wonderful stay!"
The price is ¥45,675
¥91,279 total
includes taxes & fees
Jun 29 - Jun 30
Pool Beach Supplies Outdoor Shower PingPong Table

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

9.0 out of 10, Wonderful, (174)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
The price is ¥21,605
¥72,996 total
includes taxes & fees
Jun 22 - Jun 23
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Lookout Cottage Across street from Beach and Heated Pool

10.0 out of 10, Exceptional, (1)
"The place was beautiful, tastefully furnished and decorated, and so clean! Plenty of towels and nice sheets. Loved the amenities like the pool and the beach chairs. The best part is the location - right across the street from a fantastic beach, close enough to walk to the main business district but not so close that you have to deal with all the people of you don’t want to. Perfect place for a couple looking for some R&R!"
The price is ¥33,610
¥59,687 total
includes taxes & fees
Jun 22 - Jun 23
Lookout Cottage Across street from Beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
The price is ¥38,136
¥65,380 total
includes taxes & fees
Jun 22 - Jun 23
Nook Cottage Across street from beach and Heated Pool

The Inn On Siesta Key

3.5 star property
10.0 out of 10, Exceptional, (179)
"A very accommodating property. Very clean and well maintained. The staff are extremely helpful and friendly. Great location."
The price is ¥29,903
¥39,197 total
includes taxes & fees
Jun 22 - Jun 23
The Inn On Siesta Key

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

9.8 out of 10, Exceptional, (30)
"Fun stay, great location"
The price is ¥21,750
¥35,670 total
includes taxes & fees
Jun 23 - Jun 24
Light filled walk to bay 1 King BR,1 BA private cottage by the Ringling Museum

Stylish 2BR Retreat| Walk 2 Downtown |Patio+Bikes

10.0 out of 10, Exceptional, (3)
"The property was so well appointed with a cute decor. Everything was clean and well stocked with necessities. Enjoyed our visit, highly recommend!"
The price is ¥22,446
¥52,770 total
includes taxes & fees
Jun 23 - Jun 24
Stylish 2BR Retreat| Walk 2 Downtown |Patio+Bikes

The "Grouper"

9.6 out of 10, Exceptional, (29)
"My stay was absolutely wonderful! The location is great, very convenient. The place itself is extremely comfortable, cozy, and it had everything we needed. The hosts were kind and attentive. It was truly worth every minute."
The price is ¥14,355
¥30,591 total
includes taxes & fees
Jun 22 - Jun 23
The "Grouper"

Steps to Beach+bikes VaCay getaway on PaG island

10.0 out of 10, Exceptional, (10)
"Clean and convenient to all of Pass A Grill beach, Dt Pete’s beach and surrounding area. Freebee picks you up and takes you back which is a great option for dinning. Host had all information needed for a great stay. Only small thing was 1 of the bikes seat was loose and kickstand doesn’t stay up so it was unbridle but all was great other then that."
Steps to Beach+bikes VaCay getaway on PaG island

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

9.8 out of 10, Exceptional, (37)
"Super cute little getaway for a couple. Great location- just a few steps to the beach! "
The price is ¥38,976
¥67,969 total
includes taxes & fees
Jul 3 - Jul 4
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Sunny PaG Island rental w/bikes-just steps2beach

9.0 out of 10, Wonderful, (17)
"Cute little beach house a short walk to the beach, property shared with several other rentals but felt peaceful and quiet. Parking is on street nearby. Convenient location to explore the St. Petersburg area."
The price is ¥22,620
¥43,251 total
includes taxes & fees
Jul 14 - Jul 15
Sunny PaG Island rental w/bikes-just steps2beach
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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Frequently asked questions

What are the best cheap cottages in Anna Maria Island?
Save cash on your next Anna Maria Island break by choosing cottages from just per night. Planning to uncover the sights and attractions of Bradenton Beach? Get comfortable at Queen's Gate Resort, a wallet-friendly option with pool sun loungers and a swimming pool. If you're traveling to Holmes Beach, Queen's Gate Resort is an excellent choice. It features a swimming pool and a garden and offers a superb opportunity to dial down the pace. Taking advantage of free attractions in Anna Maria Island will stretch your vacation dollars even further. Coquina Beach and Anna Maria Beach are visitor favorites. With the dollars you save, explore some more! 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.
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.