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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Anna Maria Island cottages

A balcony with wicker furniture, a grill, and a view of a marina with boats and greenery.

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)
"Place is great and clean. Love how smooth everything was. Jenny is easy to communicate as well"
United States
Natalia D.
The price is NZ$1,042
includes taxes & fees
6 Oct - 7 Oct
Newly Renovated Sea Breeze Cottage with Private Dock, Easy Access to Bimini Bay
A small, single-story mobile home with a front porch, a small attached garage, and a clock tower.

2. Bridge Street Beach House | Wi-Fi | Center of All

Bridge Street Beach House | Wi-Fi | Center of All
Bridge Street
10.0 out of 10, Exceptional, (5 reviews)
"Great location, clean accommodations, good communication with host. ..."
United States
leslie m.
The price is NZ$735
includes taxes & fees
26 Oct - 27 Oct
Bridge Street Beach House | Wi-Fi | Center of All
A two-story house with a green exterior, a blue door, and orange trim.

3. 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 NZ$377
includes taxes & fees
8 Oct - 9 Oct
The "Grouper"
A small, single-story house with a white exterior, a brick planter with palm trees, and a white picket fence.

4. Cozy Private Cottage, Minutes to Anna Maria Island

Cozy Private Cottage, Minutes to Anna Maria Island
Bradenton
10.0 out of 10, Exceptional, (13 reviews)
"Clean and nice place"
United States
Ismael
The price is NZ$407
includes taxes & fees
6 Oct - 7 Oct
Cozy Private Cottage, Minutes to Anna Maria Island
A patio with two blue lounge chairs, a potted plant, and a gravel area.

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 NZ$598
includes taxes & fees
6 Oct - 7 Oct
Pet-friendly Bradenton Home 1.5 Mi to Cortez Beach
A balcony with two wooden chairs and a small round table, surrounded by white railings and palm trees.

6. Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.4 out of 10, Exceptional, (28 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 NZ$609
includes taxes & fees
7 Oct - 8 Oct
Sunny PaG Island rental w/bikes-just steps2beach
A pair of stacked front-loading washing machines in a commercial setting.

7. Beach View 100ft To Beach and SPA

Beach View 100ft To Beach and SPA
2.0 star property
Siesta Key Village
The price is NZ$635
includes taxes & fees
8 Oct - 9 Oct
Beach View 100ft To Beach and SPA
A yellow building with a blue door and a white staircase.

8. 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, (33 reviews)
"Such a great place to stay at a beautiful location! Will be back for sure!"
United States
Erin W.
The price is NZ$638
includes taxes & fees
6 Oct - 7 Oct
Pass-a-Grille Beach Getaway| Walkable| Bikes +Gear
A white house with a covered porch, surrounded by a gravel driveway and various tropical plants.

9. 3716 7th Ave W

3716 7th Ave W
3.0 star property
Bradenton
The price is NZ$4,925
includes taxes & fees
5 Nov - 6 Nov
3716 7th Ave W
A single-story house with a blue exterior, a front door, and a small porch area.

10. 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 NZ$471
includes taxes & fees
12 Oct - 13 Oct
Coastal Breeze Cottage in Sunny Sarasota. Pet friendly. King size bed.
A bedroom with a bed, a ceiling fan, a window with curtains, a wooden wardrobe, and a framed picture on the wall.

11. Cozy Lido Studio by Beach & St Armand's

Cozy Lido Studio by Beach & St Armand's
Lido Key
The price is NZ$861
includes taxes & fees
31 Oct - 1 Nov
Cozy Lido Studio by Beach & St Armand's
A small, light blue single-story house with a front door, a garage door, and a small porch area.

12. 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 NZ$650
includes taxes & fees
6 Oct - 7 Oct
St Pete/gulfport Tiny little small home
Shared sunbathing deck by the pool, at the resort.

13. 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 NZ$610
includes taxes & fees
6 Oct - 7 Oct
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
A residential house with a white fence, a palm tree, and a parked car.

14. 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.
The price is NZ$541
includes taxes & fees
6 Oct - 7 Oct
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
A beach with tall grasses in the foreground and a sunset over the ocean.

15. An oasis ACROSS THE STREET FROM THE BEACH :)

An oasis ACROSS THE STREET FROM THE BEACH :)
Sunshine Beach
10.0 out of 10, Exceptional, (16 reviews)
"Perfect location, quiet, and close to the beach. Looking forward to coming back again. "
Canada
Richard
The price is NZ$563
includes taxes & fees
6 Oct - 7 Oct
An oasis ACROSS THE STREET FROM THE BEACH :)
A rustic building with a sign reading "The Hut Grill" and a covered outdoor seating area.

16. Order up relaxation ACROSS The STREET FROM The BEACH :)

Order up relaxation ACROSS The STREET FROM The BEACH :)
Sunshine Beach
10.0 out of 10, Exceptional, (34 reviews)
"Perfect location, perfect accommodations! Will be staying here again."
United States
Billy H.
The price is NZ$563
includes taxes & fees
6 Oct - 7 Oct
Order up relaxation ACROSS The STREET FROM The BEACH :)
A building with a tiled roof, a door, and two windows with shutters. There are two white chairs outside.

17. 🐾 1 BR Beach Cottage | Pet Friendly I Unit 8

🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
Sunset Beach
The price is NZ$941
includes taxes & fees
6 Oct - 7 Oct
🐾 1 BR Beach Cottage | Pet Friendly I Unit 8
A bedroom with a large bed, multiple pillows, and a wall-mounted artwork of tropical leaves.

18. Happy Hour ACROSS THE STREET FROM THE BEACH

Happy Hour ACROSS THE STREET FROM THE BEACH
Sunshine Beach
10.0 out of 10, Exceptional, (12 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 NZ$557
includes taxes & fees
6 Oct - 7 Oct
Happy Hour ACROSS THE STREET FROM THE BEACH
A modern house with a driveway, a tree with purple lighting, and a white car parked in front.

19. 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 NZ$809
includes taxes & fees
8 Oct - 9 Oct
Escape near Siesta Key with Hot Tub, BBQ, and Fire pit
A wooden deck with a glass door leading to a lake view, surrounded by greenery.

20. Siesta Heron 6 / Sunset

Siesta Heron 6 / Sunset
3.0 star property
Siesta Key
The price is NZ$1,279
includes taxes & fees
26 Oct - 27 Oct
Siesta Heron 6 / Sunset
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

Via Roma Beach Resort

Via Roma Beach Resort

8/10 Good
"Hot water in the shower didn’t work. No response from anyone until 23hours after checkout. Otherwise everything was wonderful."
jeff 2-night trip
Posted 1 hour ago
Via Roma Beach Resort

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
427
Accommodation
59 Cottages
Lowest Price
NZ$377
Highest Price
NZ$4,925

Frequently asked questions

What are the best cheap cottages in Anna Maria Island?
With cottages starting at only NZ$377 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.

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