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Cheap Vacation Rentals in Anna Maria Island

(19 rentals)
Anna Maria Island Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
10 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

A guest had this to say: "Songbird is a cute little purple house on a quiet side street on Anna Maria Island. I referred to the house as little, it is really quite spacious & comfortable. This is our 6th stay at Songbird & we are looking forward to our next stay. This trip we were on side ...

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Featured review

"Splendor in the sun"

Second time staying here and actually lucked out with a cancellation. 2 week stay and couldn’t have been better timing weather wise. Short couple block walk to the pristine white sand beaches. Easy haul ...

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$123
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 0.5 miles to Manatee Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bed/2bath condo on second floor, fits up to four guests, close to the gulf beach. Turnkey furnished and spruced by the owner. Shops and restaurants are close by. Trolley stop for free rides on the island is around the corner. Come and enjoy!Just remodeled and equipped with more than everything ...

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Featured review

"Fabulous stay on Anna Maria Island"

This condo was the PERFECT place for our family of three to enjoy Anna Maria Island! It was clean, cozy, and had everything we needed! Carla was a wonderful host who was very accommodating and gracious ...

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$125
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private- On second floor with covered stairs. No elevator.- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin ...

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Featured review

"Great condo!"

We enjoyed our stay! The condo was clean, spacious & inviting! The location was wonderful. We will definitely stay again. The owner was very quick to reply to my emails.

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$125
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.

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Featured review

"Queens Gate rentals-Neptune"

We had a great time. Kathy and Peter were amazing hosts who took care of our every need. We will be back again.

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$127
avg per night
Anna Maria Island Townhome
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds and sunsets you'll remember for the rest of your life. This beautifully remodeled 1 bedroom/1 bathroom condo has everything you will need to make everlasting memories of adventure ...

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Featured review

"close to white sandy beach"

Everything you would need for a beach vacation. The beach front cafe had live entertainment nightly, a perfect place for sunsets.

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$140
avg per night

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Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Paradise!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities like a heated pool, private screened lanai, and easy access to the beach, dining, and ...

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Featured review

"Great Property"

The property had everything we needed. It was very cozy! We loved the location and how it was within walking distance to everything we wanted to do. The pool was amazing! We hope to return!

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$145
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

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Featured review

"Fantastic vacation all around"

This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people. ...

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$149
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

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Featured review

"Great location, beautiful condo and excellent restaurants."

First time to Anna Maria Island and we really enjoyed it. We usually stay in Siesta Key but I think we found a new favorite area. The pool was very nice at this property and the beach is right across ...

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$150
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

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Featured review

"Great location!"

We've been on Ana Maria Island before; it's a lovely area. This was a great location for us and the management was very prompt and considerate whenever we contacted them. Thank you so much!

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$153
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to paradise on beautiful Anna Maria Island! Sunbow Bay 209 is a newly furnished 2 bedroom 2 bath condo with new appliances and coastal decor overlooking a peaceful serene lagoon with kayak and canoe access directly to the intercoastal waterway.Enjoy stunning sunrises with a cup of coffee on ...

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$158
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units ...

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Featured review

"Great place to stay"

We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road. ...

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$162
avg per night
Anna Maria Island Cottage
Sleeps 4, 2 bedrooms, 2 bathrooms
21 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Rentals by owner
  • WiFi

About this property

My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the ...

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Featured review

"Old Florida Gem"

Loved the old Florida vibe! A hop and skip to the beach - just what we were looking forward to! Sure beats a condo high rise!

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$183
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

View all property information

$192
avg per night
Last Minute Deal
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

This spacious 2 bedroom condo is close to the beach and in the heart of it all. This stunning condo offers everything you want in a beach retreat. The unit has ample space your family. The open concept living area is perfect for entertaining, with a kitchen featuring all new appliances. You can also open ...

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Featured review

"Enjoyed our stay at Sand & Surf"

Cute condo in a GREAT location. Clean with a coastal vibe. Well stocked kitchen with great appliances. Beach is walkable but we drove as there usually was parking available. The pool at this complex is ...

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$192
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

View all property information

Featured review

"Pure PLEASURE"

Such a wonderful location right across from the beach, unit was spacious, clean everything use need. Anna Maria is so special the sunsets are amazing, it's walkable for restaurants, shopping. I've been ...

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$193
avg per night
Anna Maria Island Apartment
Sleeps 4, 1 bedroom, 1 bathroom
22 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This 1 BR, four-guest, condo strategically placed within short walks to the Beach (900ft, 275M), Marina (150ft, 46M), Historic Bridge Street (800ft, 245M), and Pier (1,056ft, 322M) will keep you CHEERFUL your entire stay! Coastal amenities: front screened lanai, heated pool, beach toy closet (including ...

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$194
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

View all property information

$198
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

View all property information

$198
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Please note that the condo complex is currently an active construction site, and the following amenities are unavailable until further notice: Pool, shuffleboard, fitness center, picnic areas, bbq grills, and bayside boat dock. For updates on construction progress and amenity availability, please contact ...

View all property information

Featured review

"Excellent beach vacation"

Such a pleasant stay, great location for walking to restaurants, shops, steps from the beach. We loved staying on the island it's been years since we've been and really appreciated all that it has to offer. ...

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$199
avg per night
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