Cheap Vacation Rentals in Anna Maria Island

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

2
last minute deal
LAST MINUTE DEAL 9/28 - 10/5: A really beautiful beachy looking condo that is well maintained.

$123

avg/night

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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

"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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DEAL

2 BR | 1 BA | Sleeps 4 | Quick View

10

$130

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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$130

avg/night

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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
  • 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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$130

avg/night

View Details

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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$136

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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2 BR | 2 BA | Sleeps 6 | Quick View

2
owner special
Owner special: Tons of fall availability at extremely affordable rates!

$144

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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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 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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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

21

$170

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

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

4
last minute deal
LAST MINUTE DEAL 9/4 - 10/16: Fall availability at reduced prices!! Ground Level!

$173

avg/night

View Details

Key Amenities

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

About this property

Relax with the whole family at this peaceful place to stay.Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach.We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs!Endless ...

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Property Type

Anna Maria Island Condo

"Great Place, Perfect Location"

My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...

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DEAL

2 BR | 1 BA | Sleeps 6 | Quick View

4.7 rating on other travel sites

$182

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

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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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 | 2 BA | Sleeps 4 | Quick View

owner special
Owner special: Free Day Giveaway! Book 14 days ONLY pay for 12 days - No Saturday check in required

$190

avg/night

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Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Shell Game has been transformed into a fun and stunning tropical retreat that offers 1,154 sq. ft. of spacious living area with a newly upgraded kitchen.Located in the sought after complex of Playa Encantada; Shell Game is a tropical beach front community on the white sandy beaches of Anna Maria ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pool

About this property

Welcome to Sun Plaza West 101! *Highlighted Amenities** Location! Gulf Front Resort Condo Community! * 2 Bedrooms / 2 Bathrooms * 1 King Bed & 2 Twin Beds (Or can make 1 King upon request) * Open Air Balcony off Master Bedroom * Screened Lanai with Patio Furniture * 3rd Balcony with view ...

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Property Type

Anna Maria Island Condo

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Key Amenities

  • Air conditioning
  • Kitchen
  • Pool
  • Rentals by owner

About this property

Enjoy beautiful Anna Maria Island relaxing in a spacious ground floor condo unit with 2 bedrooms and 2 baths overlooking the heated community pool. This quiet slice of paradise has a large screened lanai off the living room with a pool view. Enjoy the amazing white sand beach and gorgeous sunsets within ...

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Property Type

Anna Maria Island Apartment

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3 BR | 2 BA | Sleeps 6 | Quick View

$199

avg/night

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Key Amenities

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

About this property

Perfect view of Beach from deck across the street, walk to all .

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Property Type

Anna Maria Island Condo

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2 BR | 2 BA | Sleeps 4 | Quick View

6

$200

avg/night

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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

"Amazing view and great host"

Terry's home is in a perfect location, with a great view, comfortable beds, and within walking distance of so many great places. I'll definitely book with him again!

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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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Anna Maria Island Vacation Rentals