Cheap Vacation Rentals in Anna Maria Island

(21 rentals)
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2 BR | 2 BA | Sleeps 4 | Quick View

1

$127

avg/night

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner

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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Property Type

Anna Maria Island Apartment

"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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2 BR | 1 BA | Sleeps 4 | Quick View

10

$131

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Rentals by owner

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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Property Type

Anna Maria Island Cottage

"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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$137

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

35 Steps to the Sea at Runaway Bay 112 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen ...

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Property Type

Anna Maria Island Condo

"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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$137

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

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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Property Type

Anna Maria Island Townhome

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

When it's time to run away— to escape to a tropical island oasis where the bright sun is shining and the gentle sea breezes are endless— then it's time to book a stay at Runaway Bay 117. This cozy coastal hideaway is tucked within one of the most exclusive Anna Maria Island communities ...

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Property Type

Anna Maria Island Condo

"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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$137

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Pool

About this property

35 Steps to the Beach at Runaway Bay 104 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen ...

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Property Type

Anna Maria Island Condo

"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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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Anna Maria Island Condo

"Great stay!"

We really enjoyed our suite. Our balcony faced the bay and the ocean was just across the street. We loved having a full kitchen and living area to make our vacation feel more like home. Thank yo for a ...

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2 BR | 2 BA | Sleeps 6 | Quick View

$169

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

About this property

Dans Florida Condos Sea Esta, located within Runaway Bay, a lovely private community on beautiful grounds with private beach access to the Gulf of Mexico.The highlight of our community is the largest heated salt water pool on the island! The condo grounds highlight tennis/pickleball courts, bocce ...

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Property Type

Anna Maria Island Apartment

"Wonderful condo, great location"

The location is great, right across street from beach. Trolly stop nearby to ride around the beach and get off at other stops for free. Places to eat within walking distance. Nice pool and tennis courts. ...

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Anna Maria Island Condo

"Stunning Accommodation"

We arrived, looking forward to a three day trip to the island. We were delighted to find this beautiful apartment was situated in a lovely quiet area but close to the free trolley bus stop and Publix supermarket. ...

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2 BR | 2 BA | Sleeps 4 | Quick View

20

$177

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Rentals by owner

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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Property Type

Anna Maria Island Cottage

"Beach cabin"

So close to the water for someone with gait issues. We always enjoy our stay here. So close to restaurants and beach. Best of both worlds

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This cozy beach condo has been updated and features a lovely open floor plan, 2 bedrooms/2 bathrooms as well as a lanai ideal for enjoying quality time together after a fun day at the beach. The outdoor closet offers beach chairs, a beach cart, beach umbrellas and toys for the littles ones to enjoy. Everything ...

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Property Type

Anna Maria Island Condo

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$182

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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Property Type

Anna Maria Island Condo

"Great vacation rental!"

My husband and I rented this condo, Sand & Surf, from Owner, Morgan Henderson, and we were completely pleased with the accommodations. Morgan was wonderful about replying immediately to any questions we ...

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2 BR | 2 BA | Sleeps 4 | Quick View

5

Distance to beach: 0.5 miles to Manatee Beach

$186

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

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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Property Type

Anna Maria Island Condo

"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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2 BR | 1 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$191

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Private pool
  • Rentals by owner

About this property

- 7 min. walk to beach, beach chairs, umbrellas, towels, beach wagon provided- sleeps 4, 2 bedroom/2 bath, very private and quiet- all linens provided, washer/dryer in unit- stores within short walk; Publix, Walgreens, CVS, Dollarama, Dunkin Donuts/ Baskin Robbins, beach stores, Ace Hardware, ...

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Property Type

Anna Maria Island Condo

"Hayward by the Sea"

The unit was very clean and the location was secluded and quiet while also being a short walk to the beach, Publix, shops and restaurants. There is also a garage to park 2 cars. The center of Anna Marie ...

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2 BR | 2 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$198

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Run to the Sun is a 2 bedroom/2 bathroom updated condo located in the sought after Runaway Bay community and has breathtaking bay views. Everything you need to complete your ideal beach getaway, can be found at Runaway Bay! Runaway Bay is a Gulf to Bay complex that is less than a 1/2 block away from the ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Bay Bliss is a 2 bedroom/2 bathroom second level, recently updated condo at Runaway Bay. Runaway Bay is a bay front complex that is less than 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated pool and spa. From ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Come relax and enjoy this stunning 2 bedroom/2 bathroom second level, recently updated condo at Runaway Bay. Runaway Bay is a bayfront complex that is less than a 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The ...

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Property Type

Anna Maria Island Villa

"Great stay!"

We loved our stay at this unit. It was very comfortable, convenient to the beach and loved the roof top seating area with a beautiful view of the beach.

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2 BR | 2 BA | Sleeps 4 | Quick View

5

$200

avg/night

View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Oceanfront
  • Rentals by owner

About this property

This is a two bedroom house on Anna Maria island, and faces the bay side. The water is literally 20 ft from your back door. Looking from your private dock to the north is the Manatee bridge, the Skyway bridge and a view of St Pete. Looking to the south you see the Cortez bridge and beyond to Sarasota. ...

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Property Type

Anna Maria Island House

"Manatee Cove"

Great location. Great view. Great everything! Can't wait to come back. Terry is great and we appreciate the work that went in to the clean up after Hurricane Ian so we could fall in love with this place. ...

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Anna Maria Island Vacation Rentals