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Anna Maria Island Vacation Rentals

(276 rentals)
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom/2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line finishes...

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$294
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool. Upon entry, you will find the open...

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Featured review

"Perfect Property"

Our stay at Blue Lagoon was perfect. The condo was very clean and had absolutely had everything you needed. The beds were very comfortable. The private home pool was so relaxing and inviting.

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$226
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Enjoy the perfect beach getaway in this beautifully updated 3-bedroom, 2-bath condo, designed to comfortably accommodate up to six guests. Thoughtfully renovated with modern finishes, the space offers a bright, open layout ideal for relaxing after a day in the sun. Located directly on Holmes Beach, this...

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$263
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

NEWLY RENOVATED! Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground level canal front home has everything you need to make this your best Anna Maria Island vacation ever. This home offers a private heated pool overlooking the mangroves and canal, private...

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$297
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

Located right across the street from the world-famous Anna Maria Island beaches, this two-bedroom condo is newly remodeled and updated and is less than 100 steps away from the warm turquoise gulf waters and sparkling white sand. Tropical Sunset #2 is one of only four units in the entire building and also...

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Featured review

"Amazing Location"

Perfect location, beach was less busy because we were far enough away from the public beach area. Plenty of space to set up and not be on top of other people. The condo itself is good and had everything...

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$190
avg per night

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Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Amazing views from the living room and primary bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on your private balcony and watch the incredible sunsets. This beautiful condo sits right on the beach in Holmes Beach. After a day on the beach, take a dip in the community pool or sit...

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$275
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1.5 bathrooms
12 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Rentals by owner
  • WiFi

About this property

Shady Palms is a cozy secluded beach cottage right on the beautiful Gulf of Mexico. Walk out the back door to a white, sugar-sand beach and the sparkling Gulf waters. Shady Palms is the most perfect spot you'll ever find on the beach - have the best of both worlds - the sun and the shade.Beach...

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Featured review

"Pure Magic"

What a special place. The memories of years line the walls with incredible family. The views simply can’t be captured with a camera even though we tried many times. The sunsets can’t be described and...

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$477
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$302
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located on the tranquil beaches of Anna Maria Island, Sandy Turtle is mere steps away from the beach and offers picturesque views of the Gulf of Mexico. The only thing distancing the balcony from the sand is a large, heated, shared swimming pool. This condo is one of the few originals left on the island...

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$383
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$707
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
7 reviews

Distance to beach: 100 yards to Manatee Beach

Key Amenities

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

About this property

Welcome to our home away from home on the breathtaking Anna Maria Island in the charming town of Holmes Beach Florida. Anna Maria is a barrier island on the Gulf of Mexico with an old time feel.Its only 7 miles long by 3 miles wide.Our condo is on the beach roughly 200 yds from the Gulf.We...

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Featured review

"Perfect Location"

The condo faced the water and lovely beach with a nice covered outside area on the second floor. This made our stay enjoyable no matter the weather. Manatee Beach was next door making easy access to food...

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$314
avg per night
Special Offer
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything...

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Featured review

"Fabulous on beach condo"

This 3 bedroom, 2 bath condo in Holmes Beach was a fabulous place for our vacation of 6 retirees. From the spacious living area, open kitchen, sunny lanai, pool and good size bedrooms to being located...

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$292
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Flirty Flamingo — a tranquil retreat on beautiful Anna Maria Island. This inviting duplex home is the ideal spot for couples, families, or friends looking to enjoy the island’s sun-soaked charm and relaxed pace.Each level of the duplex are full floor units (lower and upper...

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$235
avg per night
Anna Maria Island House
Sleeps 14, 7 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Blue Azure special: Concierge Collection Property Golf cart included on any reservation made after 6/18/26! Bradenton Beach on Anna Maria Island - 4 min walk to Gulf Beaches Pool / spa, rooftop deck Putt putt golf, ping pong, corn hole, Connect 4 Lower level refrigerator Gas...

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$672
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Wake up just steps from the sugar-white sands and sparkling shoreline in this beautifully updated coastal retreat. Perfectly positioned across the street from the beach, this inviting 2-bedroom, 2-bathroom condo offers the ideal blend of comfort, style, and convenience.Inside, the space feels light,...

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$204
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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Featured review

"Better than i expected."

Wonderful house. Very clean and well stocked. The pool was clean and big. Very close to a very nice beach. Would stay here again.

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$519
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This is it - Paradise! This fabulous Key West style elevated 3 bedroom/2 bath single family home has so many wonderful features it is hard to list them all here. It offers an elevator, cathedral ceilings, open floor plan, private heated pool & spa, private decks from every room, screened covered deck,...

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Featured review

"Great all around."

This house was everything and more. Way bigger than pictures. Had everything you could need. Would definitely stay there again.

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$248
avg per night
Special Offer
Anna Maria Island Condo
Sleeps 7, 3 bedrooms, 2 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Blue Skies" at Bradenton Beach Club!Discover your perfect getaway in this beautifully updated three-bedroom, two-bath condo, designed for families and friends looking to unwind in style. With coastal decor and modern furnishings, you’ll feel right at home from the moment...

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Featured review

"Perfection"

We absolutely loved Blue Skies at Bradenton Beach! The location was perfect, the condo was spacious and it had everything we needed. We loved the storage closet in the parking area, this made trips to and...

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$201
avg per night
Anna Maria Island Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sun Plaza West is a beautiful beachfront property offering all of the conveniences you would want in an island stay. This recently updated and remodeled 2 bedroom/2 bathroom condo offers beachfront views and is located in the heart of Holmes Beach featuring an elevator, heated pool, on-site tennis court...

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Featured review

"Sun plaza west unit 215"

One of the best sunsets views on Ami clean well maintained condo, the grounds have been updated the tenants are wonderful we look forward to coming back every year

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$248
avg per night
Anna Maria Island House
Sleeps 12, 5 bedrooms, 6 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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$575
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Coastal Serenity has a rooftop deck, private pool and spa, and an EV Charger! This single family home boasts 4 bedrooms and 3.5 bathrooms and is only a three minute walk to the beach. Beautifully decorated, the kitchen is fully-equipped with a wet bar and an island with ample counter space allowing for...

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$501
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

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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Featured review

"Great place to stay"

Sweet Freedom #237 was a great time for us. Just enough Clean space and room for everything we brought with us. Kitchen fuly equipped and bathroom shower was an added plus!! We loved the location! Hopefully,...

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$139
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Less than a minute's walk to the beach!Watch the sunset from the house!King sized bed in every bedroom.PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone!Shell House is a two-story, 3-bedroom, 2-bath, multi-level fun-house on a extra large...

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Featured review

"Great Two Weeks in Holmes Beach"

I lived in Holmes Beach for many years. It was always my favorite place to be. When I needed to move I promised myself I would rent and come as often as I could. SunPlaza West has always been my go to...

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$400
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Aqua Blu is a newly remodeled 2 bedroom/2 bathroom gulf front condo that offers everything you will need for a carefree getaway including a heated community pool and spa. From the moment you walk in, you are welcomed by stunning gulf views. Your private balcony will be the perfect resting place both day...

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$272
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Kai Blue is located in Holmes Beach, just steps from the beautiful AMI beaches. This 4 bedroom/2.5 bathroom with an elevator also has a private backyard with a pool. Kai Blue gives you the dreamy coastal vibe and it's close to restaurants, Island stores and right next to the free trolley stop.Pull...

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$325
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Colorful and inviting with a vibrant tropical style, Carefree Cottage is a perfectly-named oasis in Holmes Beach where all of your cares melt away the moment you walk through the front door. Located on a quiet residential street that offers plenty of peace and privacy yet keeps you close to the beaches...

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$364
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect coastal getaway on beautiful Holmes Beach, just one block from the shimmering Gulf of Mexico with its turquoise-blue waters and powdery white sand. This charming 3-bedroom, 2.5-bath single-family home captures the essence of Anna Maria Island living, featuring soft pastel interiors...

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$289
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Perfect for a family vacation or a couple's retreat, this newly listed and newly updated, furnished 2 bedroom/2 bath duplex is located on the north end of desirable Holmes Beach. This home offers all the comforts of home and is just steps to the beautiful white sandy beach. The kitchen is fully equipped...

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Featured review

"Rum Dog"

Overall, I was happy with this place. We stayed there two years ago. It is located a block from the gulf. The beach is nice and quiet. The house is very nice with two walk in showers.Area for improvement...

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$154
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

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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Featured review

"Our stay between Christmas and New Years"

We really enjoyed our stay at Runaway Bay. The outside of the complex looks pretty dated but the condo was freshly renovated. We had everything we needed to enjoy our stay. We appreciated all the beach...

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$152
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Reef Romance special: - Concierge Collection Property - Golf cart included! - Three houses from beautiful beaches on Anna Maria - Heated pool / separate covered spa, outdoor shower - Grill (propane included) - Putt-putt golf - Professional Linen Services - Complimentary...

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$593
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

This beautiful property offers a perfect blend of indoor and outdoor living, with welcoming accommodations for a maximum of 6 guests, all just a short walk to the pristine white sand beaches and centrally located on Anna Maria Island!The decor is a perfect blend of coastal elegance and comfort, featuring...

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$348
avg per night
Anna Maria Island House
Sleeps 16, 6 bedrooms, 4 bathrooms
10 reviews

Distance to beach: 45 feet to Gulf of Mexico

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Enjoy breathtaking views of Egmont Key, Tampa Bay, and the Gulf of Mexico right from your doorstep! Walk straight ahead and you are on North Bay Boulevard Beach. Walk 4 more lots to the left and you are on Bean Point! Or walk 5 lots further left and you are on the Gulf of Mexico. Perfectly situated next...

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Featured review

"Location is the big draw- beware stairs"

Review Serenity by the SeaThe Good 1. Location by the ocean is definitely the big draw- - can hear waves from 2 bedrooms- 1 on second and 1 on 3rd floor. No TVs in ocean view bedrooms in case that...

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$701
avg per night
Last Minute Deal
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
60 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

I try to work with your budget!- please inquire!!! If our cottage is booked, I help people with other cottages- you will love it!Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find...

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Featured review

"Quick response"

As soon as I started searching for rentals, Linda reached out and assisted me with some great options.

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$261
avg per night
New
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sailfish Nest A, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax...

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$283
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Sandcastle By The Sea special: Holmes Beach on Anna Maria Island - Short walk to Gulf Beaches Spacious heated pool / spa Outdoor seating including a fire pit Gas grill (propane included) Professional Linen Services Complimentary WiFi Beach chairs, beach wagon, & beach...

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$304
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$350
avg per night
Anna Maria Island House
Sleeps 14, 5 bedrooms, 5 bathrooms
3 reviews

Distance to beach: 0.1 miles to Bayside Beach

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • Private pool
  • Rentals by owner
  • WiFi

About this property

Newly renovated December 2024, with state of the art finishes! 5 King BR, 1 also has a Daybed + 2 King Sleeper Sofas, 1.5 Chaise Lounger, 5 BA Duplex with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! 3 King Bedrooms and 3 Bathrooms...

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Featured review

"Family holiday"

Fabulous location and spotlessly clean family villa with every conceivable convenience to hand. Fitted our purposes exactly and the addition of the kayaks, boat and bikes/golf cart if you wanted them was...

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$623
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Looking for a great vacation location on beautiful Holmes Beach? Then look no further. Island Haven is a two-story, private home that features 4 bedrooms (two of which are primary bedrooms), 3 full bathrooms, game room and private saltwater, heated pool. Upon entry, you will find the open-concept living...

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$349
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped kitchen and a stunning backyard perfect for outdoor entertaining. Ideally located near the beach, shops and restaurants, it offers the perfect blend of comfort, convenience and relaxation.Step...

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Featured review

"Awesome home!!"

The house and all the amenities were perfect!! The kitchen, dining area, bar seating at island and being open to family room was really nice!! The bedrooms were spacious, having own bathrooms was great...

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$360
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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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$155
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
8 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sailfish Nest B, a beautifully remodeled 2-bedroom, 2-bath duplex located in the heart of Holmes Beach—just a short stroll from the pristine white sands of Anna Maria Island.Step inside to discover a thoughtfully designed, open-concept living space with all-new furnishings. Relax...

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$284
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come enjoy this 2 bedroom/2 bath duplex that can sleep up to 6 people with the add-on of the sleeper sofa. Blue Lagoon is located on North Shore which is just a few blocks from the renowned shopping and dining of Pine Avenue and features a large, shared heated pool, and an EV charger. Upon entry, you...

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Featured review

"Blue Lagoon South"

We stayed at Blue Lagoon South on AMI!!!! This place was amazing for my children and I. Very clean and cozy!!! Modern!

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$225
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your ultimate beachside escape! This beautifully renovated 2 bedroom, 2 bathroom condo offers the perfect blend of modern style, comfort and location. Whether you're here for a quick escape and a longer stay, "Days Like This" at Runaway Bay 116 offers everything you need for...

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$153
avg per night
Special Offer
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

New Paint, Furniture and Decor as part of our mini makeover! King in primary bedroom and queen in second bedroom!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...

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Featured review

"Beautiful place"

Sandy Point condo was the perfect spot for our getaway! It was clean, comfortable, and in a great location—close to everything but still nice and quiet. We loved the easy beach access and relaxing by...

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$132
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Looking for a prime location to vacation? Seagrass Flats Unit 2 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops; vinyl plank flooring...

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Featured review

"Would stay again"

I want to start by saying the accommodations were nice and the location is excellent. We would stay here again. The rest of my comments or for the rental company, owner and future renters. The check in...

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$170
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

View all property information

$864
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Step into island luxury at this beautifully renovated 2-bedroom, 2-bath vacation retreat, perfectly situated just across the street from the white-sandy shores of Bradenton Beach on Anna Maria Island. Located on the lower level for easy access, Margaritaville at Runaway Bay 137 is a light, bright, and...

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$152
avg per night
Anna Maria Island Cottage
Sleeps 4, 1 bedroom, 1 bathroom
26 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation!Sailfish Gulf Suites is comprised of 4 separate suites. Suite 3 has garden views and is just a few steps to the beach.It features 1 bedroom with king size...

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$220
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Bring your family and guests to this 2-unit house! About 40 steps to the beach entrance of Anna Maria white, sandy beach, this home combined boasts 5 bedrooms, a sleeper sofa and 5 bathrooms. Bean Point Unit A boasts 3 bedrooms/3 bathrooms, while Unit B has 2 bedrooms/2 bathrooms. Both units feature well-equipped...

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$547
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...

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Featured review

"Family vacation"

We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...

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$688
avg per night
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Anna Maria Island Weather

 | 

7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

FAQ

How many vacation rentals are there in/around Anna Maria Island?

There are 276 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $89 per night with an average price per night of $284.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 199 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 24 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!