Search Cottages in Anna Maria Island

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Check prices for these dates

In two weeks
2 Jan - 4 Jan
In two months
13 Feb - 15 Feb
In three months
13 Mar - 15 Mar
In four months
10 Apr - 12 Apr

Our top choices for Anna Maria Island cottages

Exterior
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 €828
includes taxes & fees
3 Jan - 4 Jan 2026
Adorable Cottage with Covered Balconies and Private Pool
Exterior
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 €774
includes taxes & fees
15 Jan - 16 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 €965
includes taxes & fees
24 Dec - 25 Dec
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

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 €322
includes taxes & fees
22 Dec - 23 Dec
The Inn On Siesta Key
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 €277
includes taxes & fees
1 Jan - 2 Jan 2026
7mi to Anna Maria Newly Renovated Private Cottage
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 €184
includes taxes & fees
22 Dec - 23 Dec
The "Grouper"
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.
The price is €284
includes taxes & fees
4 Jan - 5 Jan 2026
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
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 €344
includes taxes & fees
22 Dec - 23 Dec
St Pete/gulfport Tiny little small home
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 €213
includes taxes & fees
22 Dec - 23 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)
"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.
The price is €425
includes taxes & fees
19 Jan - 20 Jan 2026
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
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 €292
includes taxes & fees
6 Jan - 7 Jan 2026
Escape near Siesta Key with Hot Tub, BBQ, and Fireplace
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 €271
includes taxes & fees
28 Dec - 29 Dec
Sunny PaG Island rental w/bikes-just steps2beach
Beach nearby, sun-loungers, beach towels
An oasis ACROSS THE STREET FROM THE BEACH :)

Cottage in Sunshine Beach

An oasis ACROSS THE STREET FROM THE BEACH :)
10.0 out of 10, Exceptional, (16)
"Perfect location, quiet, and close to the beach. Looking forward to coming back again. "
Canada
Richard
The price is €247
includes taxes & fees
23 Dec - 24 Dec
An oasis ACROSS THE STREET FROM THE BEACH :)
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 €354
includes taxes & fees
22 Dec - 23 Dec
Cozy 2BR Cottage Steps2 Pier, Vinoy, Beach Dr+Bikes
Terrace/patio
Nook Cottage Across street from beach and Heated Pool

Cottage in Siesta Key

Nook Cottage Across street from beach and Heated Pool
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.
The price is €618
includes taxes & fees
22 Dec - 23 Dec
Nook Cottage Across street from beach and Heated Pool
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.
The price is €955
includes taxes & fees
22 Dec - 23 Dec
Cabana Cottage Across street from Beach and Heated Pool
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 €432
includes taxes & fees
22 Dec - 23 Dec
5 star Guest House heated pool on the water!
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 €286
includes taxes & fees
22 Dec - 23 Dec
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
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 €709
includes taxes & fees
29 Dec - 30 Dec
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

Pelican Post at Anna Maria Island Inn

Pelican Post at Anna Maria Island Inn

10/10 Excellent
"Safe, clean and very comfortable "
Joshua 1-night trip
Posted 21 hours ago
Pelican Post at Anna Maria Island Inn

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
444
Accommodation
61 Cottages
Lowest Price
€184
Highest Price
€965

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 favoured by travellers. 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 €184 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 cosy charm of a cottage is perfect for holidaying 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 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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