Anna Maria Island Vacation Rentals with Private Pool

(116 rentals)
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Anna Maria Island House
2 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 4 bathrooms

$2071

avg/night

$2,071
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

LimeFish is a luxurious newly remodeled 3 bedroom (1 king-sized, 1 queen-sized, and a bunk room)/3 bathroom single level home right on the sands of Anna Maria Island. Additional sleeping accommodations can be added with the sleeper sofa in the living room. It is a perfect destination for a trip with family ...

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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

$1243

avg/night

$1,243
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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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

$917

avg/night

$917
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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

$405

avg/night

$405
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 House
3 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4 bathrooms

$1207

avg/night

$1,207
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located at the north end of Anna Maria Island, this 3 bedroom/3.5 bath home offers unique and well-appointed surroundings to make your trip memorable. Custom finishes, light fixtures, and furnishings were all handpicked to make this home truly one of a kind. The main level offers two guest suites, a living ...

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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

$578

avg/night

$578
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Manatee Lookout is a charming 3 bedroom/3 bath home with a private heated pool located on the sought after north end of Anna Maria Island. This home has everything you need for the perfect vacation and is only a short walk to the white sandy beaches. Upon entry, you have the living room where you can ...

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Property Type

Anna Maria Island House

Featured review

"Awesome beach!"

We enjoyed our trip to Anna Maria. Very quant, quiet beach. Beautiful clear water and amazing sunsets. Can’t wait to go back!!!

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

$497

avg/night

$497
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Located just a few sandy steps from the turquoise Gulf of Mexico, Seaglass Cottage is the Anna Maria Island beach house you've been dreaming about. This quintessential beachfront bungalow has a footpath across the street that leads directly to the sugary white sand of Bean Point — one of the ...

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Property Type

Anna Maria Island Cottage

Featured review

"Great place!"

Super cozy! Great place for a perfect vacation! Definitely will be one of my choices when we plan our next vacation!

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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

$2460

avg/night

$2,460
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 House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6.5 bathrooms

$856

avg/night

$856
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 Insurance Surfer's Dream boasts 4 bedrooms, 6 full bathrooms, and 1 half bath, and is also pet-friendly! This ...

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Anna Maria Island House

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

$1054

avg/night

$1,054
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 House
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms

$517

avg/night

$517
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 House
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

$459

avg/night

$459
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to "Come Sail A Bay"! Bring your boat and gear because this charming single-level home boasts 3 bedrooms and 3 bathrooms, situated on the canal just a few homes away from the open bay! With a minimum stay of 30 nights, "Come Sail A Bay" offers stunning waterfront views the ...

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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

$478

avg/night

$478
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
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms

$1541

avg/night

$1,541
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 Townhome
5 BR | 4 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

$735

avg/night

$735
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

202 69 th Street - Holmes Beach - FL 34217 VRC Book with confidence: You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that ...

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Property Type

Anna Maria Island Townhome

Featured review

"Lovely stay"

Another family and ourselves rented the property. We found it very clean and equipped to a high standard. The pool and jacuzzi were great and well used especially by the kids. The management company were ...

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Anna Maria Island House
4 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 4 bedrooms, 3 bathrooms
4.7 rating on other travel sites

$905

avg/night

$905
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

If you're looking for the perfect spot to drop anchor on Anna Maria Island— look no further than this spacious four-bedroom oasis. Located on the idyllic north end, Anchor Splash is a short stroll from the white sandy beaches and warm, aquamarine gulf waters. It's also within walking distance ...

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Property Type

Anna Maria Island House

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

$929

avg/night

$929
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
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

$552

avg/night

$552
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a den where the kids can hang out with a TV and sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island vacation! ...

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Property Type

Anna Maria Island House

Featured review

"Nice house"

This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk 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

$602

avg/night

$602
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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
3 reviews

$867

avg/night

$867
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

VRC If Guest needs to shorten their stay or change to a different property, the normal cancellation policy applies. No changes are permitted during the stay. This stunningly built and decorated 4 bedroom + Bunk Den 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico ...

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Property Type

Anna Maria Island House

Featured review

"Pleasantly surprised"

We rented this house for a family vacation. This house is everything you see & more. We found it to be perfectly located from beach/stores/restaurants in a quite neighborhood. The house was perfectly ...

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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

$1237

avg/night

$1,237
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
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

$659

avg/night

$659
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$397

avg/night

$397
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Kokomo, formerly known as OHasis, is a 2 bedroom/2 bathroom bungalow with a heated pool and private, tropical backyard. Ideal location being steps from the Gulf of Mexico, Come relax & enjoy this oasis in Holmes Beach! Step inside and see the high cathedral ceilings with an open living space. An open-concept ...

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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

$392

avg/night

$392
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
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1145

avg/night

$1,145
avg per night
View Details

Key Amenities

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

About this property

6605 Gulf Drive Holmes Beach, FL 34217 VRC19-00290 Right across the street from the beach and the Beach Bistro! Gulf Views available from this beautiful home. This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen with gas stove, wine bar, roof top deck with sweeping views ...

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Property Type

Anna Maria Island House

Featured review

"Ideal family vacation home!"

The property was great, and worked really well with our family-which includes a 4 year old and a 9 month old, so having the bedrooms in different areas and private baths, made everything much easier. Centrally ...

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Anna Maria Island House
5 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 6.5 bathrooms
4.8 rating on other travel sites

$1125

avg/night

$1,125
avg per night
View Details

Key Amenities

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

About this property

Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 3.5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 3.5 bathrooms
21 reviews

Distance to beach: 0.2 miles to bradenton beach

$729

avg/night

$729
avg per night
View Details

Key Amenities

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

About this property

You will fall in love with this peaceful retreat. This home comes with a 6 person golf cart. You will love zooming around the island on the golf carts, window shopping at all of the gorgeous real estate. This unit is within walking distance to the beach, you will love being able to walk back and forth ...

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Property Type

Anna Maria Island House

Featured review

"Wonderful first experience to AMI"

This rental is everything you could dream of. A short walk to the beach and all the extras you could ever need. The golf carts were our favorite for evening strolls along the island. Taylar really thought ...

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

$479

avg/night

$479
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
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 3 bathrooms

$839

avg/night

$839
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

C-View is the perfect island getaway for your family vacation. Conveniently located within walking distance to Anna Maria's picturesque white sand beaches, Pine Avenue's restaurants and shops, and access to the free trolley. Be sure to bring your kayaks and paddle boards so you can take advantage ...

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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

$710

avg/night

$710
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Stonehenge is a massive stone monument in southern England. Here in the U.S. on Anna Maria Island, ...

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Property Type

Anna Maria Island House

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

$1207

avg/night

$1,207
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Beachfront, North End, large 2 bedroom with expansive views of the dolphins frolicking in the azure waters of the North End of Anna Maria Island. BBQ grill, bikes, paddle boards, and kayaks are all included. Your backyard is a beautiful view of Egmont Key & the Skyway Bridge and your front yard is ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms

$898

avg/night

$898
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 MADE AFTER 1/24/24 WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Coastal Serenity has a rooftop deck, private pool and spa, and an EV Charger! ...

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Property Type

Anna Maria Island House

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

$493

avg/night

$493
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Palms is a recently renovated and remodeled 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 where you can relax and read a book or ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$671

avg/night

$671
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This is where you will make Island Memories! Situated less than a 2 minute walk to the white, sandy beaches of Anna Maria, The 3-bedroom, 2-bathroom layout is perfect for families or groups of friends, accommodating up to 8 people comfortably. Step inside and you'll know you're on vacation with ...

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Property Type

Anna Maria Island House

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Anna Maria Island House | On the beach
6 BR | 4 BA | Sleeps 12 | Quick View
Sleeps 12, 6 bedrooms, 4 bathrooms

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

This upper and lower unit duplex home is located steps from the Gulf of Mexico on historic Anna Maria Island. These Holmes Beach bungalows have a large heated pool and are rented in unison, perfect for friends and large families, as well. Both units are pet friendly. Only 1/2 mile from shops and restaurants ...

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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

$1039

avg/night

$1,039
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 Insurance Summer 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
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 bedrooms, 8.5 bathrooms
2 reviews

$1506

avg/night

$1,506
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.7 rating on other travel sites

$443

avg/night

$443
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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 boat deck, ...

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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

$507

avg/night

$507
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 MADE AFTER 1/24/24 WITH A CHECK-IN DATE AFTER 4/9/24! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance After a day out on your boat or riding on your jet skis, you have plenty ...

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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

$2542

avg/night

$2,542
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
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 bedrooms, 6 bathrooms

$1422

avg/night

$1,422
avg per night
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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
4 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
4.7 rating on other travel sites

$588

avg/night

$588
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 Insurance Looking for a great vacation location on beautiful Holmes Beach? Then look no ...

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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

$790

avg/night

$790
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 | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$473

avg/night

$473
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 House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$345

avg/night

$345
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. The 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 of the trolley stops for guests to hop on ...

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

$874

avg/night

$874
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 Insurance Located 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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.9 rating on other travel sites

$424

avg/night

$424
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior showcases island artwork, creating a welcoming and calming environment. ...

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Property Type

Anna Maria Island House

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

$2321

avg/night

$2,321
avg per night
View Details

Key Amenities

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

About this property

Beach Front/Heated Pool/Hot Tub/ 4 bedroom plus den North End of Anna Maria Island. Professionally decorated and finished with all King Beds and En-Suite Bathrooms. Chef's Kitchen with a 48inch gas range. Wine Cooler on two levels and a private covered porch to enjoy the sunsets on the upper levels. ...

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Property Type

Anna Maria Island House

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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

$880

avg/night

$880
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 Insurance This 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
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

To Book Directly please visit: /its-miller-time If you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team: This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen ...

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Property Type

Anna Maria Island House

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