Anna Maria Island Vacation Rentals

(227 rentals)
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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$253

avg/night

$253
avg per night
View Details

Key Amenities

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

About this property

Enjoy Anna Maria Island from this fresh and casual 2 bedroom, 2 bath poolside condo in Runaway Bay!Just steps from the beach and the bay, Runaway Bay has it all – a heated, salt water pool (the largest on the island!), tennis, bocce ball and shuffleboard courts, a work out room, clubhouse and ...

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Property Type

Anna Maria Island Condo

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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

$651

avg/night

$651
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 InsuranceDream Weaver is an amazing, custom luxury home nestled in the quiet residential ...

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Property Type

Anna Maria Island House

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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

$1665

avg/night

$1,665
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 House
8 BR | 6.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6.5 bathrooms
1 review

$2521

avg/night

$2,521
avg per night
View Details

Key Amenities

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

About this property

Paradise Beach lives up to its name! Nestled directly on the pristine soft white sands of Bradenton Beach, this remarkable property boasts 8 bedrooms, 6.5 bathrooms, and is pet-friendly. Complete with an elevator, it comfortably accommodates up to 18 guests. Bring your family and friends along to experience ...

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Property Type

Anna Maria Island House

Featured review

"Margaritaville Themed Paradise with 2 King Beds & Incredible Lanai!"

Truly an amazing resort and we loved staying in Sunset Seacret! Our family enjoyed every minute! We looked hard to find a beautiful, safe, clean, beachy condo with 2 king beds, as we were vacationing with ...

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Anna Maria Island Condo
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom
4.7 rating on other travel sites

$224

avg/night

$224
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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

$334

avg/night

$334
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Completely updated 3 bedroom/2.5 bath townhome located in the Bermuda Bay Community. Bermuda Bay is a beautiful Gulf to Bay property that is located directly across the street from the white sandy 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 Townhome

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

$877

avg/night

$877
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 | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
54 reviews

$1221

avg/night

$1,221
avg per night
View Details

Key Amenities

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

About this property

Discover Serendipity: Your Pet-Friendly Beachfront Haven on Anna Maria Island Beachfront Bliss Awaits You Indulge in the enchantment of beachfront bliss at Serendipity, an exceptional 4-bedroom home perfectly positioned on the coveted North End of Anna Maria Island. This tranquil escape beckons you ...

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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

$417

avg/night

$417
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

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

$227

avg/night

$227
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$333

avg/night

$333
avg per night
View Details

Key Amenities

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

About this property

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 brand new (2018) luxurious heated pool and spa, ...

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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 Condo
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$411

avg/night

$411
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Welcome to Bella Luna, where you'll find a beachfront condo boasting two bedrooms and two bathrooms, complete with access to a heated community pool and spa. Whether you prefer basking in the sun on the beach or enjoying the breathtaking Gulf views from indoors, this is the perfect retreat. And don't ...

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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
1 review

$580

avg/night

$580
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to La Isla Bonita; New home under our management!- Steps to Anna Maria Island's powdery-white sandy beaches - Private heated pool, ping pong table, and basketball game - Impressive deck with breathtaking views - 4 spacious bedrooms & 4 bathrooms - 3-story home with elevator - ...

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Property Type

Anna Maria Island Villa

Featured review

"Seas the Day"

Great accommodations..good location to shopping, marina, Anna Maria Island, restaurants.. quick response from Mgmt Team for minor issue.. quiet area, carport, security gate.. enjoyed our time there..

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
last minute deal
LAST MINUTE DEAL 4/19 - 4/26: 4 bedroom Island Pool Home Fully stocked. Just Bring your clothes! Discounted for Easter Week

$586

avg/night

$586
avg per night
Offer for: Apr 19 - Apr 26:
4 bedroom Island Pool Home Fully stocked. Just Bring your clothes! Discounted for Easter Week

View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Heated salt water pool. Baby and beach equipment, BikesVRC# #This listing, A Lazy River Day and Night includes Both sides of home.Cleaning fee includes Professional Linen Service for all towels and bedding!A leisurely stroll (less than three short blocks) from the blissful beaches of ...

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Property Type

Anna Maria Island House

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

$372

avg/night

$372
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 Condo
2 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms
4.8 rating on other travel sites

$277

avg/night

$277
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Crisp, clean, and completely remodeled— this 2 bedroom townhome is the perfect spot to make unforgettable Anna Maria Island memories. The warm sand and turquoise water of the Gulf of Mexico are right across the street. You'll be steps away from the beach and a quick stroll or bike ride from ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$503

avg/night

$503
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking distance ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$469

avg/night

$469
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

213 76th St. Bradenton Beach, Fl 34217 VRC “You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property” We ...

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Property Type

Anna Maria Island House

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

$511

avg/night

$511
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Approximately 40 steps and you'll be at the beach entrance to Anna Maria's sandy, white beach. This property offers convenient access to one of the island's main attractions. As the upper level of a two-unit home, Bean Point Residence Unit A boasts 3 bedrooms/3 bathrooms, providing ample ...

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Property Type

Anna Maria Island Villa

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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

$351

avg/night

$351
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • 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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
44 reviews

$1305

avg/night

$1,305
avg per night
View Details

Key Amenities

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

About this property

Welcome to your Gulfside, bohemian escape! Serendipity Gulf’s minimalistic, peaceful approach to decor strips away all the unnecessary to leave you with a serene oasis out to the beach that lies just beyond the back door. The clean, white decor within the home leaves plenty of opportunity for your ...

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Property Type

Anna Maria Island House

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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

$916

avg/night

$916
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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$812

avg/night

$812
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
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
4.9 rating on other travel sites

$729

avg/night

$729
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 House
9 BR | 10 BA | Sleeps 18 | Quick View
Sleeps 18, 9 bedrooms, 10 bathrooms

$2360

avg/night

$2,360
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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
5.0 rating on other travel sites

$232

avg/night

$232
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 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 ...

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Property Type

Anna Maria Island Condo

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

$714

avg/night

$714
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
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$172

avg/night

$172
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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 House
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6 bathrooms

$1413

avg/night

$1,413
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 4/27/23! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance.Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, ...

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Property Type

Anna Maria Island House

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

$438

avg/night

$438
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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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

$225

avg/night

$225
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2.5 bathrooms

$280

avg/night

$280
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

Sunset Landings Unit 5 is a spacious 2 bedroom/2.5 bath townhome with amazing views of the Gulf of Mexico. With just a few steps across the street, you can enjoy the white sandy beaches and numerous fishing piers. There are no buildings to obstruct your view of the beach!This beautiful townhouse sleeps ...

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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

$645

avg/night

$645
avg per night
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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Anna Maria Island House
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms

$516

avg/night

$516
avg per night
View Details

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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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

$261

avg/night

$261
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
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$352

avg/night

$352
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 Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4.7 rating on other travel sites

$554

avg/night

$554
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 Townhome
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$155

avg/night

$155
avg per night
View Details

Key Amenities

  • Air conditioning
  • WiFi

About this property

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

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Property Type

Anna Maria Island Townhome

Featured review

"close to white sandy beach"

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

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

$361

avg/night

$361
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This amazing beachfront 2 bedroom/2 bathroom condo is perfect for an island vacation. This unit is recently under new ownership and has been completely updated with new paint throughout, all new kitchen appliances and brand-new living room and dining room furniture. The unit features a fully-equipped ...

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Property Type

Anna Maria Island Condo

Featured review

"Breach front paradise"

This is our 3rd vacation on AMI and we love it! This condo is a perfect location with beautiful beach and water views. So close you can watch dolphins from the balcony! The rooms are good, master bed very ...

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

$1089

avg/night

$1,089
avg per night
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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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Anna Maria Island House

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

$877

avg/night

$877
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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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 House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
5.0 rating on other travel sites

$415

avg/night

$415
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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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
2 reviews

$364

avg/night

$364
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Casa Del Mar is a beautiful Key West-style home featuring 4 bedrooms/2.5 bathrooms. This property is located on the north end of Holmes Beach close to shopping, restaurants and trolley stops. Best of all, this unit is within walking distance to the white sandy beaches. Amenities also include heated pool, ...

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Anna Maria Island House

Featured review

"74th Street"

This is a great place to stay! Easy walk to the beach. Super nice rental. Seabreeze was responsive to all questions and concerns.

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4.5 bathrooms

$1087

avg/night

$1,087
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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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
1 review

$354

avg/night

$354
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your ...

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Property Type

Anna Maria Island Condo

Featured review

"Tropical Sunset #1"

Location is where it's at! Close to everything, yet on a quiet street. We had a great time celebrating 5 years post cancer! Loved the Island and everyone on it. We didn't want to leave! Loved the way ...

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

$368

avg/night

$368
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 | 6 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6 bathrooms

$3356

avg/night

$3,356
avg per night
View Details

Key Amenities

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

About this property

Welcome to Shangri-La, an idyllic vacation rental nestled on the exclusive tip of Anna Maria Island at Bean Point. This luxurious, fenced, and gated private property offers an escape from the everyday, inviting you to unwind and rejuvenate in a setting of unparalleled beauty and comfort. Available for ...

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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

$560

avg/night

$560
avg per night
View Details

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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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

$612

avg/night

$612
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 Vacation Rentals

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°

Enjoy the Perfect Anna Maria Island Getaway


Looking for a gorgeous and relaxing Anna Maria Island vacation rental without leaving the Florida coast? Anna Maria Island is the perfect vacation spot for you. Anna Maria Island is located on Florida’s western shore, just a few miles south of St. Petersburg.

This small, quaint island is separated from mainland Florida by the waters of Palma Sola Bay and Anna Maria Sound. However, the coast is connected to the island by way of U.S. Highways 64 and 684, making it easy to travel between the two. Despite its size, Anna Maria Island is packed with activities to enjoy and many gorgeous rental homes.

With FloridaRentals.com, you can live like a local while on your vacation by enjoying authentic architecture from the inside out within Anna Maria Island’s residential neighborhoods.

Hotel stays can be enjoyable, but there’s nothing quite like a high-quality rental home while on vacation. Not only will your trip feel more immersive within Anna Maria Island’s unique energy, but you will also be able to truly relax while on your trip.

There is no worrying about sharing a wall with strangers or lacking privacy. Additionally, you’ll be able to relax in a private backyard with some much-needed peace and quiet. Many Anna Maria rentals with FloridaRentals.com even feature unique amenities like pools, hot tubs, entertainment centers, walkable beach access, and much more.

Anna Maria Island Travel Tips


If you’re planning a trip to Anna Maria Island, you should keep a few key details in mind. The first is which airport you plan on flying into. Anna Maria Island is reachable by car from many of Florida’s largest cities, including St. Petersburg, Clearwater, Tampa, and Sarasota. However, depending on where you live, traveling to Anna Maria Island by plane might be easier.

There is no airport on the island, so you will have to fly into a nearby city and rent a car or take public transport from there. The closest commercial airport to Anna Maria Island is the Sarasota Bradenton International Airport, which is about 16 miles south of the island.

The St. Pete-Clearwater International Airport can also connect to Anna Maria Island via I-275 across Tampa Bay. This option is less convenient as this airport is about 45 miles north of the island. However, by flying into St. Pete–Clearwater, you could bundle multiple popular Florida destinations into one trip by taking the “long way.”

Another detail to keep in mind is the climate. Though many Florida cities experience warm weather throughout the year, the best time to enjoy the outdoors with warm yet pleasant temperatures on Anna Maria Island is mid-spring or fall. During these times of the year, average temperatures are between 80 and 85 degrees Fahrenheit, and chances of precipitation are low.


Best Eats on Anna Maria Island


There are many incredible restaurants and bars on Anna Maria Island, many featuring beachfront views. Rod and Reel Pier is a great example. Located on the northernmost tip of Anna Maria Island with a full menu of seafood and cocktails.

City Pier Grill and Bait, located on the end of Anna Maria Pier, is another great local spot for a meal with family, drinks with friends, or a romantic date. The delicious globally-inspired seafood dishes are complemented by the gorgeous view of Tampa Bay, which is especially breathtaking at sunset.

As you travel farther south down the island, there are many more eateries to explore during your visit to Anna Maria Island. Scott’s Deli is a great choice for fresh and delicious sandwiches if you’re looking to grab something quick to take for a picnic lunch on the beach.

Nearby are Duffy’s Tavern and Freckled Fin Irish Pub, two local bars that serve their own unique menus of American favorites and ice-cold drinks. If you’re looking for a more upscale after-dinner drinks experience, The Doctor’s Office is a hip cocktail bar in central Anna Maria with plenty of imaginative cocktails and light bites to enjoy. And yes, the building used to be a real doctor’s office!


Things to Do Near Anna Maria Island Vacation Rentals


Despite its small size, there is a huge variety of beaches to explore near Anna Maria Island rentals. Manatee Public Beach, located on the southwestern side of the island, is a popular destination for white sand, warm waters, and plenty of fun in the sun.

As you travel even farther south to the neighborhood of Bradenton Beach on Anna Maria Island, you’ll find spots like Coquina Beach, which wraps around the southern tip of the island. For prime beach access on the island’s northernmost tip, Bean Point Beach and Bayfront Park are two of the most popular. Many of the island’s beaches have a variety of amenities, such as playgrounds, volleyball nets, picnic tables, and concession stands.

The many Anna Maria Island piers are a special way to experience the beauty of the area from the water (without getting wet!). Some of these include Rod and Reel Pier, the Anna Maria City Pier, and Bridge Street Pier. Visitors can find local art and culture, gift shops, restaurants, and stunning views at any of the island’s piers.

Aside from taking a stroll along a pier, there are many other ways to experience the shimmering waters of Tampa Bay or the Gulf of Mexico. One popular activity for vacationers is to rent a boat or kayak from one of the many vendors along the island’s shores.

One of Anna Maria Island’s most popular rental shops is Beach Bums. At Beach Bums, you can rent kayaks and paddle boards for the whole family or even book a special kayak tour led by an experienced local. Need a break from the water? You can also rent bicycles or golf carts to explore Anna Maria Island by land!

Experience Bliss on Anna Maria Island


Adventure is waiting for you on Anna Maria Island. Make the most out of your adventure by vacationing at a luxurious private home, courtesy of FloridaRentals.com.


FAQ

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

There are 227 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 $127 per night with an average price per night of $469.

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 141 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 18 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!