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Check prices for these dates

Next weekend
2 Jan - 4 Jan
In two weeks
9 Jan - 11 Jan
In one month
23 Jan - 25 Jan
In two months
20 Feb - 22 Feb

Our top choices for Anna Maria Island cottages

Exterior
Romantic Island Getaway! Just Steps from the Beach

Cottage in Bradenton Beach

Romantic Island Getaway! Just Steps from the Beach
2.0 star property
8.8 out of 10, Excellent, (3)
"It was great! Check in was super easy and anything you would need is nearby. "
United States
Thomas N.
The price is NZ$1,231
includes taxes & fees
28 Dec - 29 Dec
Romantic Island Getaway! Just Steps from the Beach
Terrace/patio
Adorable Cottage with Covered Balconies and Private Pool

Cottage in Anna Maria

Adorable Cottage with Covered Balconies and Private Pool
9.6 out of 10, Exceptional, (41)
"Amazing cottage with plenty of amenities and a fantastic location. Just a few minutes walk to the beach, shopping and restaurants. Check-in and check-out were a breeze. The only hiccup was issues with parking. Often the single reserved space below was taken by restaurant clients."
United States
C. S.
The price is NZ$1,548
includes taxes & fees
3 Jan - 4 Jan 2026
Adorable Cottage with Covered Balconies and Private Pool
Outdoor dining
Beautiful Guest House Near the Beach with Private Pool!

Cottage in Anna Maria

Beautiful Guest House Near the Beach with Private Pool!
8.6 out of 10, Excellent, (30)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
The price is NZ$1,472
includes taxes & fees
16 Jan - 17 Jan 2026
Beautiful Guest House Near the Beach with Private Pool!
Exterior
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

Cottage in Anna Maria

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
10.0 out of 10, Exceptional, (1)
"Absolutely lovely place to stay. The four of us were SO comfortable. The place was clean and beautiful. Very well maintained. You can tell by the high quality finishes that this is someone’s home and they maintain it as such. There was an unforeseen circumstance that popped up with the island doing some work that affected the house while we were there. I messaged the owner and within minutes he had replied and had all the necessary people on the way to fix it. They fixed it all while we were at...
United States
Devon F.
The price is NZ$1,649
includes taxes & fees
6 Jan - 7 Jan 2026
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

Cottage in Bradenton

7mi to Anna Maria Newly Renovated Private Cottage
10.0 out of 10, Exceptional, (3)
"I stayed for 9 days. It was in a great location in Bradenton...just minutes from the beach, shopping and dining. It was clean and quiet. I would stay there again."
United States
MO L.
The price is NZ$508
includes taxes & fees
1 Jan - 2 Jan 2026
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
St Pete/gulfport Tiny little small home

Cottage in St. Petersburg

St Pete/gulfport Tiny little small home
10.0 out of 10, Exceptional, (3)
"The house was decorated nicely, it was clean, and inside/outside was well kept. The hosts were lovely and responded quickly to questions with precise information. If I need a place to stay in Gulfport again, I would not hesitate to stay!"
United States
Karen J.
The price is NZ$691
includes taxes & fees
27 Dec - 28 Dec
St Pete/gulfport Tiny little small home
Exterior
The "Grouper"

Cottage in Sunny Shores

The "Grouper"
9.4 out of 10, Exceptional, (43)
"A beautiful little place to stay only minutes away from the beach! Very cozy and clean! "
United States
savana w.
The price is NZ$361
includes taxes & fees
29 Dec - 30 Dec
The "Grouper"
The Lookout, 1 King Bedroom 1 Bath | Terrace/patio
The Inn On Siesta Key

Cottage in Siesta Key

The Inn On Siesta Key
3.5 star property
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
The price is NZ$767
includes taxes & fees
28 Dec - 29 Dec
The Inn On Siesta Key
Exterior
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.

Cottage in South Village

Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
9.6 out of 10, Exceptional, (81)
"We loved our stay at the Drift Inn. Very clean, just the right amount of room for 4, easy access to the beach and pool. The beds were very comfortable. The owner was very quick to respond to questions from beginning to end. We would stay here again."
United States
Kimberly P.
Drift Inn A, Heated Pool, Beach and Amenities, 2-3 min walk.
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

Cottage in Siesta Key

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
9.2 out of 10, Wonderful, (5)
"We really enjoyed the cleanliness and location. Pool was great. Having our own deck was nice. Great views. Highly recommend. "
United States
Rolly N.
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
Steps to Beach+bikes VaCay getaway on PaG island

Cottage in Pass-a-Grille

Steps to Beach+bikes VaCay getaway on PaG island
9.8 out of 10, Exceptional, (20)
"Super cute location and unit! Close parking and within walking distance to restaurants (dinner, lunch, breakfast) and soooo close to the beach! "
United States
Shaunte W.
The price is NZ$510
includes taxes & fees
28 Dec - 29 Dec
Steps to Beach+bikes VaCay getaway on PaG island
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

Cottage in Sarasota

Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
9.2 out of 10, Wonderful, (177)
"Loved this place, very roomy and even had a coffee bar, cute style, and right by the beach."
United States
Alexis
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Property grounds
Sunny PaG Island rental w/bikes-just steps2beach

Cottage in Pass-a-Grille

Sunny PaG Island rental w/bikes-just steps2beach
9.0 out of 10, Wonderful, (18)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
The price is NZ$418
includes taxes & fees
28 Dec - 29 Dec
Sunny PaG Island rental w/bikes-just steps2beach
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Cottage in Sarasota

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
2.0 star property
The price is NZ$615
includes taxes & fees
8 Jan - 9 Jan 2026
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Exterior
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota

Cottage in Bayou Oaks

Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
2.0 star property
The price is NZ$207
includes taxes & fees
26 Jan - 27 Jan 2026
Cozy 1-bedroom cottage that connects to a county park in beautiful Sarasota
Property grounds
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

Cottage in Historic Old Northeast

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
10.0 out of 10, Exceptional, (4)
"The location is great. in a few minutes you are in North Shore Park walking along Tampa Bay. The cottage was clean and cozy. We just might rent it again next time we visit family in the area."
United States
Cynthia S.
The price is NZ$681
includes taxes & fees
28 Dec - 29 Dec
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Terrace/patio
5 star Guest House heated pool on the water!

Cottage in South Sarasota

5 star Guest House heated pool on the water!
The price is NZ$849
includes taxes & fees
27 Dec - 28 Dec
5 star Guest House heated pool on the water!
Terrace/patio
Cabana Cottage Across street from Beach and Heated Pool

Cottage in Siesta Key

Cabana Cottage Across street from Beach and Heated Pool
10.0 out of 10, Exceptional, (5)
"Wonderful property and fantastic location. Everything you need at your fingertips for an enjoyable beach stay without ever having to leave the island!"
United States
Meghan J.
Cabana Cottage Across street from Beach and Heated Pool
Property grounds
Lookout Cottage Across street from Beach and Heated Pool

Cottage in Siesta Key

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!"
United States
Keeley L.
The price is NZ$1,569
includes taxes & fees
29 Dec - 30 Dec
Lookout Cottage Across street from Beach and Heated Pool
Exterior
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Cottage in Pass-a-Grille

Steps 2 Beach-Island Cottage w/king bd+2bike+parking
9.8 out of 10, Exceptional, (41)
"Quiet neighborhood away from the tourist areas. 50 steps to a beautiful white sandy beach:) charming little place, very clean and comfortable. sunsets were beautiful and almost no rain all week:)"
United States
James C.
The price is NZ$865
includes taxes & fees
2 Jan - 3 Jan 2026
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
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

Seabreeze at Anna Maria Island Inn

Seabreeze at Anna Maria Island Inn

10/10 Excellent
"Room was clean and staff was friendly "
Steven 3-night trip
Posted 3 days ago
Seabreeze at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
528
Accommodation
61 Cottages
Lowest Price
NZ$361
Highest Price
NZ$1,649

Frequently asked questions

What are the best cheap cottages in Anna Maria Island?
With cottages starting at only NZ$361 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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