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Our top choices for Anna Maria Island cottages

Exterior
Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool

Adorable Cottage with Covered Balconies and Private Pool
Anna Maria
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.
$847 nightly
The price is $946
Jan 3 - Jan 4, 2026
Total with taxes and fees
Adorable Cottage with Covered Balconies and Private Pool
Exterior
Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!

Beautiful Guest House Near the Beach with Private Pool!
Anna Maria
8.6 out of 10, Excellent, (30)
"Beautiful home perfectly located near the beach, bars and restaurants. "
United States
Bibiana G.
$784 nightly
The price is $875
Dec 23 - Dec 24
Total with taxes and fees
Beautiful Guest House Near the Beach with Private Pool!
Exterior
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool

SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
Anna Maria
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.
$933 nightly
The price is $1,039
Jan 11 - Jan 12, 2026
Total with taxes and fees
SunSalt Cottage~5 min to Beach, Shops & Restaurants~PrivatePool
The Cottage, 3 Bedroom 2 Bath (2 Kings, 1 Queen, 2 Twins) | Terrace/patio
The Inn On Siesta Key

The Inn On Siesta Key

The Inn On Siesta Key
3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (191)
"Great place to stay! "
United States
Carlos
$327 nightly
The price is $370
Dec 23 - Dec 24
Total with taxes and fees
The Inn On Siesta Key
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage
Bradenton
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.
$285 nightly
The price is $318
Jan 1 - Jan 2, 2026
Total with taxes and fees
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
The "Grouper"

The "Grouper"

The "Grouper"
Sunny Shores
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.
$189 nightly
The price is $211
Dec 29 - Dec 30
Total with taxes and fees
The "Grouper"
Outdoor dining
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed

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

Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Siesta Key
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.
$326 nightly
The price is $326
Jan 4 - Jan 5, 2026
Total with taxes and fees
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Exterior
St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home

St Pete/gulfport Tiny little small home
St. Petersburg
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.
$353 nightly
The price is $394
Dec 23 - Dec 24
Total with taxes and fees
St Pete/gulfport Tiny little small home
Exterior
Steps to Beach+bikes VaCay getaway on PaG island

Steps to Beach+bikes VaCay getaway on PaG island

Steps to Beach+bikes VaCay getaway on PaG island
Pass-a-Grille
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.
$248 nightly
The price is $265
Dec 23 - Dec 24
Total with taxes and fees
Steps to Beach+bikes VaCay getaway on PaG island
Exterior
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village

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, (177)
"my friends and I traveled from across the country to meet for our annual “girls” trip. Location is amazing. You can walk to the beach, you can rent cabanas and there are lounge chairs for your use. The pool is sparkling and the trolley stop is right outside the property entrance. I just love Siesta key and this is a wonderful place to get away from it all, but have easy access to all of the fun and shopping. "
United States
Kim C.
$441 nightly
The price is $492
Jan 19 - Jan 20, 2026
Total with taxes and fees
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace

Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
2.0 star property
Sarasota
$300 nightly
The price is $334
Jan 6 - Jan 7, 2026
Total with taxes and fees
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
Property grounds
Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach

Sunny PaG Island rental w/bikes-just steps2beach
Pass-a-Grille
9.0 out of 10, Wonderful, (18)
"Short walk to the beach and well-kept property. Very neat area."
United States
Emily M.
$249 nightly
The price is $266
Dec 28 - Dec 29
Total with taxes and fees
Sunny PaG Island rental w/bikes-just steps2beach
Beach nearby, sun loungers, beach towels
An oasis ACROSS THE STREET FROM THE BEACH :)

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)
"Perfect location, quiet, and close to the beach. Looking forward to coming back again. "
Canada
Richard
$254 nightly
The price is $284
Dec 23 - Dec 24
Total with taxes and fees
An oasis ACROSS THE STREET FROM THE BEACH :)
Property grounds
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes

Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Historic Old Northeast
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.
$401 nightly
The price is $433
Jan 20 - Jan 21, 2026
Total with taxes and fees
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Terrace/patio
Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool

Nook Cottage Across street from beach and Heated Pool
Siesta Key
10.0 out of 10, Exceptional, (4)
"They have really thought of everything and gone above and beyond to make our stay as comfortable as possible. Everything was very clean! Paige was a wonderful guide and host for the local area!"
United States
Derek N.
$664 nightly
The price is $727
Dec 23 - Dec 24
Total with taxes and fees
Nook Cottage Across street from beach and Heated Pool
Terrace/patio
Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool

Cabana Cottage Across street from Beach and Heated Pool
Siesta Key
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.
$1,005 nightly
The price is $1,086
Dec 23 - Dec 24
Total with taxes and fees
Cabana Cottage Across street from Beach and Heated Pool
Terrace/patio
5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!

5 star Guest House heated pool on the water!
South Sarasota
$444 nightly
The price is $496
Dec 23 - Dec 24
Total with taxes and fees
5 star Guest House heated pool on the water!
Exterior
Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Steps 2 Beach-Island Cottage w/king bd+2bike+parking

Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Pass-a-Grille
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.
$347 nightly
The price is $373
Dec 24 - Dec 25
Total with taxes and fees
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Property grounds
Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool

Lookout Cottage Across street from Beach and Heated Pool
Siesta Key
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.
$744 nightly
The price is $830
Dec 29 - Dec 30
Total with taxes and fees
Lookout Cottage Across street from Beach and Heated Pool
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

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

10/10 Excellent
"Place was adorable and perfect for our stay. We were walking distance from beach and close to everything we wanted to do."
Karen G. 2-night trip
Posted 3 days ago
Steps from Beach and Local Hotspots! Stay at Sunny Side Down!

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
444
Accommodation
59 Cottages
Lowest Price
$211
Highest Price
$1,086

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.
What are the best cheap cottages in Anna Maria Island?
With cottages starting at only $211 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.
Are there any family-friendly cottages in Anna Maria Island?
There are indeed. Whether it's in one of Anna Maria Island's busy cities or way out in nature, the cozy charm of a cottage is perfect for vacationing families. If Bradenton Beach is on your radar, book a stay at Queen's Gate Resort. This 2.5-star option offers a nearby beach and a barbecue grill. Another superb choice is 105b 12th Street South Front 2 Bedroom Apts By Redawning. Also in Bradenton Beach, this family-friendly cottage has a 3-star rating and includes WiFi and a barbecue grill. You'll find plenty of awesome things to do with the family in Bradenton Beach. Anna Maria Beach and Coquina Beach promise a fantastic day out.
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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