Book a Anna Maria Island Cottage

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
21 Nov - 23 Nov
In two weeks
28 Nov - 30 Nov
In one month
12 Dec - 14 Dec
In two months
9 Jan - 11 Jan

Featured Cottages in Anna Maria Island

Terrace/patio
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)
"The location was perfect with close beach access and surrounded by a lot of fun businesses. We loved being over the pizza shop, could go down there and grab food or drinks! We enjoyed our stay very much!"
United States
Sarah E.
The price is NZ$930
includes taxes & fees
14 Nov - 15 Nov
Adorable Cottage with Covered Balconies and Private Pool
Exterior
Romantic Island Getaway! Just Steps from the Beach

Romantic Island Getaway! Just Steps from the Beach

2.0 star property
Bradenton Beach
8.8 out of 10, Excellent, (3)
"Although there are laundry facilities on property, the area is kept locked and this unit is not permitted access. We were unable to do any laundry unless we traveled two miles to Holmes Beach to the Laundromat. This property IS very quiet. The trolley stops are literally at the end of the driveway, but there are no shops or businesses within close walking distance. Also, there were beach chairs and towels, but THERE ARE NO EXTRAS here, which is unlike any other Vrbo/AirBnb we have visited. There...
United States
Amy
The price is NZ$668
includes taxes & fees
11 Nov - 12 Nov
Romantic Island Getaway! Just Steps from the Beach
Exterior
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.
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

3.5 star property
Siesta Key
10.0 out of 10, Exceptional, (189)
"Room was great!!! Staffa n owner awesome!!!"
United States
Ronald
The price is NZ$466
includes taxes & fees
11 Nov - 12 Nov
The Inn On Siesta Key
Outdoor dining
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.
The price is NZ$542
includes taxes & fees
11 Nov - 12 Nov
Siesta Key Sanctuary -Pool-Kayaks-TikiHut-King bed
Property grounds
7mi to Anna Maria Newly Renovated Private Cottage

7mi to Anna Maria Newly Renovated Private Cottage

Bradenton
10.0 out of 10, Exceptional, (2)
"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$488
includes taxes & fees
11 Nov - 12 Nov
7mi to Anna Maria Newly Renovated Private Cottage
Exterior
The "Grouper"

The "Grouper"

Sunny Shores
9.2 out of 10, Wonderful, (41)
"Very clean and nice place ."
United States
Sherry S.
The price is NZ$379
includes taxes & fees
12 Nov - 13 Nov
The "Grouper"
Exterior
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, (176)
"clean, nice amenities and great location"
United States
Robert K.
The price is NZ$684
includes taxes & fees
11 Nov - 12 Nov
Siesta Key Beachside Getaway Cottage Walking Distance to Beach and Village
Exterior
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, (19)
"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$468
includes taxes & fees
12 Nov - 13 Nov
Steps to Beach+bikes VaCay getaway on PaG island
Property grounds
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)
"Wonderful stay. Everything was perfect. The location can’t be beat, 2 minute walk to a beautiful beach. 2nd visit and we’ll be back!"
United States
Valerie W.
The price is NZ$468
includes taxes & fees
18 Nov - 19 Nov
Sunny PaG Island rental w/bikes-just steps2beach
Property grounds
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK

Palmetto
The price is NZ$440
includes taxes & fees
17 Nov - 18 Nov
Florida Charm Minifarm🐓 HotTub-POOL-Chickens! Near I75, I275. Pets, trailers OK
Property grounds
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.
The price is NZ$643
includes taxes & fees
11 Nov - 12 Nov
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

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.
The price is NZ$1,088
includes taxes & fees
11 Nov - 12 Nov
Nook 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!

South Sarasota
The price is NZ$905
includes taxes & fees
11 Nov - 12 Nov
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

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.
The price is NZ$608
includes taxes & fees
4 Dec - 5 Dec
Steps 2 Beach-Island Cottage w/king bd+2bike+parking
Pool
Nest Cottage Across street from beach and Heated Pool

Nest Cottage Across street from beach and Heated Pool

Siesta Key
10.0 out of 10, Exceptional, (2)
"Clean, modern and staff is amazing. Room ready before noon received text notification from owners. This is now our new go to after 19 years of staying up the street. All of everything is provided in rooms and for beach life, well maintained and fun atmosphere no pressures except to make memories here."
United States
Marti C.
The price is NZ$944
includes taxes & fees
19 Nov - 20 Nov
Nest Cottage Across street from beach and Heated Pool
Terrace/patio
Haven cottage Across street from beach and Heated Pool

Haven cottage Across street from beach and Heated Pool

Siesta Key
9.8 out of 10, Exceptional, (7)
"Enjoyed the property, a very nice little unit, very clean and enjoyable"
United States
Michael M.
The price is NZ$944
includes taxes & fees
18 Nov - 19 Nov
Haven 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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Anna Maria Island Hotel Reviews

Bali Hai Beachfront Resort and Spa

Bali Hai Beachfront Resort and Spa

10/10 Excellent
"By far our best stay down here so far!! "
Tabitha 1-night trip
Posted 2 days ago
Bali Hai Beachfront Resort and Spa

Find out more about Anna Maria Island

Anna Maria Island Cottages information

Number of reviews
Accommodation
 Cottages
Lowest Price
Highest Price

Frequently asked questions

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

Explore a world of travel with Expedia