An aerial view of a coastal town with a long pier extending into turquoise waters.

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Check prices for these dates

In two weeks
18 Sep - 20 Sep
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Anna Maria Island cottages

Exterior

1. 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 AED 924
AED 3,144 total
includes taxes & fees
11 Sep - 12 Sep
Beautiful Guest House Near the Beach with Private Pool!
Exterior

2. Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
9.8 out of 10, Exceptional, (51 reviews)
"Pleasantly surprised how great this place was - awesome backyard setup and incredible location "
United States
Cyrus M.
The price is AED 932
AED 3,404 total
includes taxes & fees
17 Sep - 18 Sep
Adorable Cottage with Covered Balconies and Private Pool
Property grounds

3. 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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is AED 1,098
AED 2,401 total
includes taxes & fees
7 Sep - 8 Sep
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Property grounds

4. 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, (29 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.
Beautiful Condo on Pine Ave, 2 Blocks to Beach
House (2 Bedrooms) | Interior

5. 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 AED 643
AED 1,234 total
includes taxes & fees
2 Sep - 3 Sep
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
Property grounds

6. Coastal Luxury 7mi to Anna Maria Private Cottage

Coastal Luxury 7mi to Anna Maria Private Cottage
Bradenton
10.0 out of 10, Exceptional, (11 reviews)
"Very nice location. "
United States
Daniel o.
The price is AED 248
AED 914 total
includes taxes & fees
2 Sep - 3 Sep
Coastal Luxury 7mi to Anna Maria Private Cottage
Exterior

7. Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear

Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Pass-a-Grille
9.8 out of 10, Exceptional, (31 reviews)
"Such a great place to stay at a beautiful location! Will be back for sure!"
United States
Erin W.
The price is AED 353
AED 1,010 total
includes taxes & fees
2 Sep - 3 Sep
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Property grounds

8. 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, (26 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 AED 375
AED 1,039 total
includes taxes & fees
16 Sep - 17 Sep
Sunny PaG Island rental w/bikes-just steps2beach
Balcony view

9. The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (206 reviews)
"The property was perfect. Walk to down town and the beach. Loved the provisions for the beach which made it so convenient. Room was super clean and overall the property was well maintained."
United States
Stephen
The price is AED 716
AED 1,013 total
includes taxes & fees
2 Sep - 3 Sep
The Inn On Siesta Key
Exterior

10. 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, (51 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is AED 555
AED 1,355 total
includes taxes & fees
14 Sep - 15 Sep
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Property grounds

11. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is AED 8,668
AED 11,333 total
includes taxes & fees
3 Sep - 4 Sep
3716 7th Ave W
1 bedroom, iron/ironing board, WiFi, bed sheets

12. Lido Bungalow Walk to Beach & St. Armand's Circle

Lido Bungalow Walk to Beach & St. Armand's Circle
Lido Key
The price is AED 323
AED 1,224 total
includes taxes & fees
2 Sep - 3 Sep
Lido Bungalow Walk to Beach & St. Armand's Circle
1 bedroom, iron/ironing board, WiFi, bed sheets

13. Cozy Lido Key Bungalow by Pool & Beach

Cozy Lido Key Bungalow by Pool & Beach
Lido Key
The price is AED 323
AED 1,224 total
includes taxes & fees
3 Sep - 4 Sep
Cozy Lido Key Bungalow by Pool & Beach
Exterior

14. 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 1,367 total
includes taxes & fees
2 Sep - 3 Sep
St Pete/gulfport Tiny little small home
Hair dryer, towels, soap, shampoo

15. Sunny Lido Studio - Modern Touches

Sunny Lido Studio - Modern Touches
Lido Key
The price is AED 364
AED 1,277 total
includes taxes & fees
2 Sep - 3 Sep
Sunny Lido Studio - Modern Touches
House (4 Bedrooms) | Interior

16. 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 507
AED 1,842 total
includes taxes & fees
7 Sep - 8 Sep
4 Mi to Dtwn St Pete! Pet-friendly Home w/ Yard
Exterior

17. 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, (90 reviews)
"Would definitely stay here again. Great location and great house! Owner was quick and helpful with communication."
United States
Clarissa S.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining

18. Cozy Lido Key Studio Steps to Beach & Kayaking

Cozy Lido Key Studio Steps to Beach & Kayaking
Lido Key
The price is AED 343
AED 1,250 total
includes taxes & fees
2 Sep - 3 Sep
Cozy Lido Key Studio Steps to Beach & Kayaking
Exterior

19. 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, (190 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is AED 795
AED 1,566 total
includes taxes & fees
2 Sep - 3 Sep
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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

Seaside at Anna Maria Island Inn

Seaside at Anna Maria Island Inn

10/10 Excellent
"Todo fue perfecto"
Marco 1-night trip
Posted 7 hours ago
Seaside 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 10.0, 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.

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