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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Anna Maria Island 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 AED 1,341
AED 2,679 total
includes taxes & fees
8 Jun - 9 Jun
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.
Beautiful Guest House Near the Beach with 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 AED 1,862
AED 4,334 total
includes taxes & fees
27 Jun - 28 Jun
Beautiful Condo on Pine Ave, 2 Blocks to Beach
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 AED 1,480
AED 4,119 total
includes taxes & fees
14 Jun - 15 Jun
Adorable Cottage with Covered Balconies and Private Pool
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 AED 364
AED 775 total
includes taxes & fees
29 Jun - 30 Jun
The "Grouper"
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 AED 551
AED 2,222 total
includes taxes & fees
8 Jun - 9 Jun
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 AED 367
AED 915 total
includes taxes & fees
18 Jun - 19 Jun
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
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 AED 526
AED 1,356 total
includes taxes & fees
8 Jun - 9 Jun
St Pete/gulfport Tiny little small home
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 AED 602
AED 1,355 total
includes taxes & fees
9 Jun - 10 Jun
Tropical Treehouse · Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Marina

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!

Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
Southgate
9.6 out of 10, Exceptional, (15 reviews)
"Place had everything needed. Host was very communicative and helpful. "
United States
Chris R.
The price is AED 331
AED 1,547 total
includes taxes & fees
30 Jun - 1 Jul
Entire Village! La Mia Casa out of Siesta Dr. Beach resort vibe!
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 AED 588
AED 1,339 total
includes taxes & fees
8 Jun - 9 Jun
Sunny PaG Island rental w/bikes-just steps2beach
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 AED 404
AED 1,094 total
includes taxes & fees
16 Jun - 17 Jun
Coastal Luxury 7mi to Anna Maria Private Cottage
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.
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
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 AED 364
AED 1,113 total
includes taxes & fees
10 Jun - 11 Jun
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Fridge, microwave, stovetop, dishwasher

Lido Key Getaway - Bikes & Beach Gear

Lido Key Getaway - Bikes & Beach Gear
Lido Key
The price is AED 356
AED 1,491 total
includes taxes & fees
21 Jun - 22 Jun
Lido Key Getaway - Bikes & Beach 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 AED 533
AED 909 total
includes taxes & fees
20 Jun - 21 Jun
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, (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 AED 705
AED 1,569 total
includes taxes & fees
8 Jun - 9 Jun
Downtown Cottage | Walk Everywhere, Park once
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, (184 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is AED 1,264
AED 2,168 total
includes taxes & fees
12 Jun - 13 Jun
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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 AED 562
AED 1,153 total
includes taxes & fees
8 Jun - 9 Jun
Happy Hour ACROSS THE STREET FROM THE BEACH
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 AED 672
AED 1,978 total
includes taxes & fees
11 Jun - 12 Jun
Unwind Poolside + Walk to Beach! Sarasota Retreat
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

The Retreat at Anna Maria Island Inn

The Retreat at Anna Maria Island Inn

8/10 Good
"Super clean, friendly cleaning staff super cozy. This is where we plan to stay when we come back."
Kimberly 4-night trip
Posted 1 hour ago
The Retreat at Anna Maria Island Inn

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.
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.