Anna Maria Island Vacation Rentals with Private Pool

(163 rentals)
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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4.7 rating on other travel sites

$519

avg/night

$519
avg per night
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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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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 5 bathrooms
41 reviews

$1752

avg/night

$1,752
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Oceanfront
  • Private pool
  • WiFi

About this property

Luxury and the beach intersect at a point titled Serendipity Deux. This gorgeous 4 bedroom home offers all the allure of an extravagantly decorated space while giving you premium beach access and an ideal location. The Master Suite is located on the first level and comes outfitted with a king bed, tub ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
4.5 rating on other travel sites

$325

avg/night

$325
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This amazing beachfront 2 bedroom/2 bathroom condo is perfect for an island vacation. This unit features a fully-equipped kitchen, elevator, washer dryer, cable TV/WiFi, shaded assigned parking and a shared heated pool spa. But, it doesn t stop there; this unit has stunning views of the Gulf of Mexico ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$320

avg/night

$320
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beach Bellini is a 3 bedroom/3 bathroom private home in Holmes Beach. Just an 8 minute walk to the beach, pull into the paver driveway with a one-car garage and enter this light and airy home with wood floors and wood plank ceilings. The fully-stocked kitchen has stainless steel appliances, granite counters, ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$659

avg/night

$659
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceWith the feel of a five-star luxury resort and the privacy of a secluded island ...

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Property Type

Anna Maria Island House

Featured review

"Very nice home"

Home was very nice. The whole backyard is like paradise. Overall great experience.Pool was not refreshing but probably expected this time of year in Florida. The hot tub flows over into pool when ...

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$201

avg/night

$201
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms

$417

avg/night

$417
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS CREATED AFTER 1/10/25! All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle Insurance.Welcome to Beach Escape! As you drive up the private driveway, you'll be enveloped by lush native plants, ...

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Anna Maria Island House

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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
3 reviews

$154

avg/night

$154
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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

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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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$395

avg/night

$395
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Found is a recently remodeled and renovated 2 bedroom/2 bath duplex with its own private heated pool & spa. This property is centrally located on Holmes Beach and only a few minutes walk to the white sandy beaches. Upon entry, you have the living room with all new furnishings, where you can ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4.7 rating on other travel sites

$474

avg/night

$474
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL RESERVATIONS THAT CHECK OUT BEFORE 1/3/26 All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceLooking for a great vacation location on beautiful Holmes Beach? Then look no further. Island Haven ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$235

avg/night

$235
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. This newly remodeled home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw from the trolley stops ...

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Property Type

Anna Maria Island House

Featured review

"great location"

We enjoyed on our stay at this well-kept property on Anna Maria Island. It offered privacy with a good central location.

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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms

$1659

avg/night

$1,659
avg per night
View Details

Key Amenities

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

About this property

Get ready to be swept off your feet by the charm and luxury of Winding Waves, your dream vacation spot right on the beautiful Anna Maria Island. This dazzling nine-bedroom, eight-and-a-half bathroom beachfront home is all about fun in the sun and upscale relaxation!Splash and Play Outdoors: Dive ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 5.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 5.5 bathrooms
1 review

$1221

avg/night

$1,221
avg per night
View Details

Key Amenities

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

About this property

Come stay at From Dusk 'Til Dune! This home is a recently built beach residence offering rooftop water views just one block away from the Gulf of Mexico beaches. This 5 bedroom, 5.5 bathroom, pet-friendly vacation haven is brimming with amenities. Its stunning backyard features a private pool, hot ...

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Property Type

Anna Maria Island House

Featured review

"Serenity on the Water"

The condo was only surpassed by the view, which included a nightly explosion of sunset glory over the sound. If one wanted to be closer to the sun from the beach, the club directly on the gulf was only ...

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.6 rating on other travel sites

$322

avg/night

$322
avg per night
View Details

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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Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$305

avg/night

$305
avg per night
View Details

Key Amenities

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

About this property

New Name - A Wave From It All, formerly known as Island Dream, is a recently updated custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 3 bedrooms/2 bathrooms. You will find that this home has everything you need for your perfect Anna Maria Island vacation! From the ...

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Property Type

Anna Maria Island House

Featured review

"Family Vaca 2023"

This was my family's first vacation to Anna Maria island. The house was beautiful and in a great location, convenient to all the hot-spots! The lay-out of the house was great, master bed and queen beds ...

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms
1 review

$769

avg/night

$769
avg per night
View Details

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceThis gorgeous, custom-built, professionally designed, private home is a 4 bedroom/6.5 ...

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Property Type

Anna Maria Island House

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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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1593

avg/night

$1,593
avg per night
View Details

Key Amenities

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

About this property

Compass Rose, a captivating residence offering deluxe amenities including a lazy-river-style pool with a hot tub, a game room, an elevator and a rooftop deck boasting amazing views of the Gulf of Mexico. This 9 bedroom, 8.5 bathroom, pet-friendly abode is an ideal beach retreat suitable for multiple families ...

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Property Type

Anna Maria Island House

Featured review

"Great location"

Very clean and comfortable. Easy walk to everything you need and want to do. I would stay there again and highly recommend.

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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$153

avg/night

$153
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

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

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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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$204

avg/night

$204
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$423

avg/night

$423
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4.5 bathrooms
4.9 rating on other travel sites

$873

avg/night

$873
avg per night
View Details

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. Driver's must provide valid US Driver's License and US Vehicle InsuranceSummer Retreat is an absolutely amazing, new, custom luxury home nestled in the quiet residential area in the heart of Bradenton ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4.5 bathrooms

$1205

avg/night

$1,205
avg per night
View Details

Key Amenities

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

About this property

Big Luxury 6 bdrm, Pool, Spa, Bikes, Kayak, Reviews, Beach!Come enjoy a large family and friends gathering at this spacious luxury home just a few minutes stroll to the beach. One of the larger homes on the island, with 6 bedrooms and 4.5 bathrooms and 3400 sq. ft, this home has plenty of room for ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
4.9 rating on other travel sites

$331

avg/night

$331
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$204

avg/night

$204
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

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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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4.9 rating on other travel sites

$325

avg/night

$325
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Beautiful 3 bedrooms/2 baths condo is in the highly sought out Bradenton Beach Club community. It has quality finishes including wood cabinets, solid granite surfaces, stainless steel appliances and quality tile in the living and bathroom areas. So well-appointed with comfortable furniture, fishing dock, ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$341

avg/night

$341
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
43 reviews

$1249

avg/night

$1,249
avg per night
View Details

Key Amenities

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

About this property

Welcome to Mintfish, your calm, canal front oasis. This getaway home marries natural elements with luxury to create the perfect vacation spot for you, your friends, and your family (even the furry members!). The ground-level, single-floor home makes relaxation accessible for anyone and everyone. Recent ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$206

avg/night

$206
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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. From the pool, ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Villa
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
5 reviews
last minute deal
LAST MINUTE DEAL 4/26 - 5/23: Availability Starting April 26th!! Contact us for special discounted rates!

$599

avg/night

$599
avg per night
Offer for: Apr 26 - May 23:
Availability Starting April 26th!! Contact us for special discounted rates!

View Details

Key Amenities

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

About this property

Are you dreaming of mornings by the pool and evenings watching sunsets on the sand? Are you travelling with little ones and need baby gear ready and waiting for you? Are you ready to trade your everyday routine for an unforgettable island escape?If this sounds like you, we’d love to welcome ...

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Property Type

Anna Maria Island Villa

Featured review

"Beautiful house and Celine is an excellent host"

Beautiful house and Celine is an excellent host. We stayed here a week for a family vacation and really enjoyed our time. House had everything we needed and more. Very clean and super close to the beach. ...

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DEAL
Anna Maria Island House
5 BR | 4.5 BA | Sleeps 16 | Quick View
Sleeps 16, 5 bedrooms, 4.5 bathrooms

$1013

avg/night

$1,013
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, where a shimmering pool and soothing spa await your relaxation. Discover the serene charm of A Bean Point Paradise, a retreat boasting 5 bedrooms and 4.5 bathrooms with parking for ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Pelican Cove is a beautiful Gulf to Bay property with a prime location just steps to the beach, five-star restaurants, shops and more - it's the tropical vacation you've been dreaming of offering you all of the conveniences you would want in an island stay. This beautiful condo was completely ...

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Property Type

Anna Maria Island Condo

Featured review

"Great Island Location"

Clean, cute updated condo. Photos represent the property correctly. Great view of the bay, right on the water. Only a short walk across the street to the beach. Easy walk (5 blocks) to great shopping ...

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

$458

avg/night

$458
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Casa Bonita is bright, inviting, and the perfect place for a wonderful vacation with family and friends in a tropical paradise. This home is located in the heart of Bradenton Beach, only a few short steps away from beachfront access and Bridge Street. You can lounge in the sun and enjoy a swim in your ...

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Property Type

Anna Maria Island House

Featured review

"Perfect"

The house was absolutely perfect! It was so nice and the cleanest house we have ever rented. We had everything we needed. We would definitely recommend.

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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$529

avg/night

$529
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

The View at the Bradenton Beach Club offers panoramic views of the Gulf of Mexico and beautiful beaches from the living room, primary suite or private screened balcony. The condo is part of the Bradenton Beach Club that provides the very best in vacation accommodations. Amenities at the BBC include two ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
8 BR | 5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 5 bathrooms
3 reviews

$740

avg/night

$740
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Look no further for your perfect vacation home for the whole family. Island Oasis is a custom-built spacious 8 bedroom/5 bathroom was professionally furnished to provide ...

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Property Type

Anna Maria Island House

Featured review

"Nice"

Very clean nice home enjoyed it...would consider renting again..thank you...talked with the owner and manager next door Great people

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Anna Maria Island Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
4.8 rating on other travel sites

$261

avg/night

$261
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Brimming with historic character, this charming ground level 1 bedroom/1 bath cottage has a bright modern, organic feel–and is merely steps from the white sandy beaches. With dramatic vaulted ceilings and secluded garden settings, The Cozzi Cottage offers everything you'd want in a beach vacation. ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
24 reviews

$1086

avg/night

$1,086
avg per night
View Details

Key Amenities

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

About this property

Escape to paradise at our stunning vacation rental, located at 230 Lakeview on beautiful Anna Maria Island. This exquisite property offers the ultimate coastal getaway, boasting a brand-new pool and spa where you can unwind and soak up the Florida sun in style.For those seeking outdoor fun, our rental ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

$556

avg/night

$556
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) ...

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Property Type

Anna Maria Island House

Featured review

"Perfect Beach House for just about anyone"

Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first ...

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms

$799

avg/night

$799
avg per night
View Details

Key Amenities

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

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER April 29, 2024! All Drivers must be over the age of 21. Drivers must provide valid US Driver's License and US Vehicle InsuranceSurfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms

$1221

avg/night

$1,221
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS CREATED AFTER 12/18/24! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance.This exquisite single-family beachfront home, perfectly positioned to offer uninterrupted Gulf of ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
4.9 rating on other travel sites

$698

avg/night

$698
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceLocated just steps away from the sugary, soft sand and clear ocean water, Salty ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
20 reviews

$204

avg/night

$204
avg per night
View Details

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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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
5 BR | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 5 bathrooms

$925

avg/night

$925
avg per night
View Details

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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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

$333

avg/night

$333
avg per night
View Details

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 cathedral ceilings, open floor plan, private heated pool & spa, private decks from every room, screened covered deck, ground level ...

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Property Type

Anna Maria Island House

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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Anna Maria Island House
9 BR | 10 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 10 bathrooms

$2343

avg/night

$2,343
avg per night
View Details

Key Amenities

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

About this property

Gather your family and friends and head to Swanky Bubbles! Swanky Bubbles can accommodate 18 people! This exquisite 9-bedroom, 11-bathroom, pet-friendly with an elevator residence is ideally situated. Just steps away from the beach and within walking distance of shopping and restaurants, you'll have ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 4 bedrooms, 4 bathrooms
4.6 rating on other travel sites

$746

avg/night

$746
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Come enjoy this 4 bedroom/4 bath duplex that can sleep up to 12 people with the add-on of the sleeper sofas. 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 in ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 6 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 6 bathrooms
1 review

$843

avg/night

$843
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show proof of US driver's license and vehicle insurance. You'll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size ...

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Property Type

Anna Maria Island House

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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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
55 reviews

$1481

avg/night

$1,481
avg per night
View Details

Key Amenities

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

About this property

Escape to Your Exclusive Tropical Retreat! Indulge in the privacy of your own backyard oasis, complete with a sprawling pool and a dedicated Beach Volleyball Court. Open the back gate and find yourself steps away from the pristine Gulf Beaches. This ground-floor haven offers unparalleled convenience, ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
5.0 rating on other travel sites

$374

avg/night

$374
avg per night
View Details

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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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$799

avg/night

$799
avg per night
View Details

Key Amenities

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

About this property

Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms
1 review

$379

avg/night

$379
avg per night
View Details

Key Amenities

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

About this property

Absolutely beautiful monthly rental in highly sought after Holmes Beach on Anna Maria Island. If you are interested in dates blocked on the calendar, please message me. This 100% updated home has everything from a large heated pool, outdoor shower, lush mature landscaping, completely furnished inside ...

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Property Type

Anna Maria Island House

Featured review

"Awesome House"

WOW! I can not say enough about the wonderful stay we had. The house was beautiful and stocked with everything a family would need and the location is perfect. Short walk to beach and Pine St. restaurants ...

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Anna Maria Island Vacation Rentals