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
2 Oct - 4 Oct
In two months
13 Nov - 15 Nov
In three months
11 Dec - 13 Dec
In four months
8 Jan - 10 Jan

Our top choices for Anna Maria Island cottages

Property grounds

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)
"Very nice property! Clean and lovely water view!"
United States
Sadie E.
The price is £421
includes taxes & fees
21 Sept - 22 Sept
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
Exterior

2. The "Grouper"

The "Grouper"
Sunny Shores
9.6 out of 10, Exceptional, (75 reviews)
"We enjoyed our stay, close to shops and beach!"
United States
Savannah S.
The price is £153
includes taxes & fees
26 Sept - 27 Sept
The "Grouper"
Property grounds

3. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (12 reviews)
"Very nice location. "
United States
Daniel o.
The price is £185
includes taxes & fees
21 Sept - 22 Sept
Cozy Private Cottage, Minutes to Anna Maria Island
House (2 Bedrooms) | Interior

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 £251
includes taxes & fees
21 Sept - 22 Sept
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
Exterior

5. Yellow Palm Cottage steps from the beach

Yellow Palm Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (2 reviews)
"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.
The price is £430
includes taxes & fees
24 Sept - 25 Sept
Yellow Palm Cottage steps from the beach
Exterior

6. Steps 2 Beach- Cottage w/king bd +2bikes +parking

Steps 2 Beach- Cottage w/king bd +2bikes +parking
Pass-a-Grille
9.6 out of 10, Exceptional, (52 reviews)
"Clean, quiet and an easy walk to the beach."
United States
Marion W.
The price is £279
includes taxes & fees
21 Sept - 22 Sept
Steps 2 Beach- Cottage w/king bd +2bikes +parking
Property grounds

7. 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, (27 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 £227
includes taxes & fees
27 Sept - 28 Sept
Sunny PaG Island rental w/bikes-just steps2beach
Exterior

8. 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 £184
includes taxes & fees
21 Sept - 22 Sept
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
Exterior

9. 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 £232
includes taxes & fees
22 Sept - 23 Sept
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
Outdoor dining

10. Studio by Lido Beach w heated pool

Studio by Lido Beach w heated pool
Lido Key
The price is £259
includes taxes & fees
1 Oct - 2 Oct
Studio by Lido Beach w heated pool
Hair dryer, towels, soap, shampoo

11. Coastal Studio, Walk to St Armand's or Lido Beach

Coastal Studio, Walk to St Armand's or Lido Beach
Lido Key
The price is £249
includes taxes & fees
21 Sept - 22 Sept
Coastal Studio, Walk to St Armand's or Lido Beach
Property grounds

12. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is £2,264
includes taxes & fees
4 Oct - 5 Oct
3716 7th Ave W
Outdoor banquet area

13. Real Florida Up Close! Family-friendly, Pet-friendly with private pool

Real Florida Up Close! Family-friendly, Pet-friendly with private pool
Sarasota
The price is £226
includes taxes & fees
21 Sept - 22 Sept
Real Florida Up Close! Family-friendly, Pet-friendly with private pool
Property grounds

14. Pink Mango Cottage steps from the beach

Pink Mango Cottage steps from the beach
Siesta Key Village
10.0 out of 10, Exceptional, (1 review)
The price is £431
includes taxes & fees
30 Sept - 1 Oct
Pink Mango Cottage steps from the beach
Exterior

15. 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 £284
includes taxes & fees
21 Sept - 22 Sept
St Pete/gulfport Tiny little small home
Exterior

16. Blue Dolphin Cottage steps from the beach

Blue Dolphin Cottage steps from the beach
Siesta Key Village
The price is £424
includes taxes & fees
24 Sept - 25 Sept
Blue Dolphin Cottage steps from the beach
Exterior

17. Escape near Siesta Key with Hot Tub, BBQ, and Fire pit

Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Sarasota
8.4 out of 10, Very good, (10 reviews)
"The house was truly lovely, and the hosts were exceptionally caring, kind, and attentive in their communication. It was wonderful to be so close to the beach, with stores conveniently nearby, making the stay feel comfortable and welcoming."
United States
Kandra R.
The price is £352
includes taxes & fees
21 Sept - 22 Sept
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
Exterior

18. 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, (191 reviews)
"Right across the beach Less then 5 minutes Good space - rooms nice ad clean "
United States
ASHISH
The price is £302
includes taxes & fees
21 Sept - 22 Sept
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds

19. Downtown Cottage | Walk Everywhere, Park once

Downtown Cottage | Walk Everywhere, Park once
Historic Old Northeast
10.0 out of 10, Exceptional, (11 reviews)
"Lovely accommodation close to everything. So many lovely restaurants and sights right you doorstep while sating in a darling cottage in a very quaint neighborhood. And just a short drive to lovely beaches. Highly recommend."
United States
Jennifer C.
The price is £249
includes taxes & fees
23 Sept - 24 Sept
Downtown Cottage | Walk Everywhere, Park once
Outdoor dining

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

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 £233
includes taxes & fees
28 Sept - 29 Sept
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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

Driftwood at Anna Maria Island Inn

Driftwood at Anna Maria Island Inn

8/10 Good
"The property was clean but the bathroom was very small. The rate was $350 and should have been under $250. We thought it would probably be a resort but was an old motel with a small pool"
Moses 1-night trip
Posted 4 hours ago
Driftwood at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
422
Accommodation
57 Cottages
Lowest Price
£185
Highest Price
£2,264

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 9.6, so you're sure to snag a place that suits your needs. Planning to stay in Bradenton Beach? Queen's Gate Resort is one property loved by guests. This 2.5-star cottage includes handy amenities such as a swimming pool and pool sun loungers. 105b 12th Street South Front 2 Bedroom Apts By Redawning is another highly rated escape where you can relax close to nature. A barbecue grill and a swimming pool are two of the conveniences you can make use of at this 3-star pick in Bradenton Beach.
What are the best cheap cottages in Anna Maria Island?
Save money on your Anna Maria Island trip by choosing cottages from just £185 per night. Planning to discover the sights and sounds of Bradenton Beach? Settle in at Queen's Gate Resort, a cheap option with a barbecue grill and a swimming pool. If you're heading for Holmes Beach, Queen's Gate Resort is a terrific choice. It features pool sun loungers and a garden and provides the perfect opportunity to dial down the pace for a while. If you're exploring Anna Maria Island and want to save money, there are lots of free and popular attractions to put on your to-do list. Anna Maria Island Museum and Historical Park and Island Gallery West 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 Island?
You'll discover some terrific family-friendly cottages in Anna Maria Island. If you're on your way to Bradenton Beach, look up Queen's Gate Resort. With useful amenities like a nearby beach and WiFi, the whole crew will enjoy putting their feet up at this 2.5-star property. 105b 12th Street South Front 2 Bedroom Apts By Redawning is also a great choice for families in Bradenton Beach. This 3-star cottage includes WiFi, a barbecue grill and more. Once you've put your bags down and settled in, it's time to discover the best of Bradenton Beach. Look forward to making memories together at family-friendly attractions such as Florida Maritime Museum at Cortez and Anna Maria Island Museum and Historical Park.
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 traveller 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 accommodation that'll make your hip pocket happy, tailor your search results by budget, amenities and star rating.

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