Beach House Vacation Rentals in Anna Maria Island

(17 rentals)
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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
12 reviews
owner special
Owner special: Available now to 3/15, 4701 3rd Ave, Holmes Beach, at reduced rate call cell or text message.

$359

avg/night

$359
avg per night
Owner special:
Available now to 3/15, 4701 3rd Ave, Holmes Beach, at reduced rate call cell or text message.

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Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

Featured review

"Great Vacation Spot. Great Owner. Awesome Location"

What an awesome place. Lots of rooms to stretch out. The 2 car garage and big drive way were nice for ease of parking and to securely store things. The large shared pool is wonderful and perfect temp. ...

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Anna Maria Island House
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1.5 bathrooms
11 reviews

$508

avg/night

$508
avg per night
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Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

Featured review

"AMAZING!!!"

This house is the best rental we have ever stayed in! The scenery out back is incredibly relaxing.. trees, Adirondack chairs, the OCEAN!! It is so private, and also the best equipped kitchen I’ve ever ...

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

$500

avg/night

$500
avg per night
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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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 0.1 miles to 30 seconds to your left

$876

avg/night

$876
avg per night
View Details

Key Amenities

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

About this property

This newly redesigned elevated 3 Bedroom, 2 Bathroom home is beautifully appointed throughout, with state of the art quartzite counter tops, stainless steel appliances and driftwood style hardwood floors and ceilings. Relax on the covered porch with direct views of the Gulf of Mexico and it's stunningly ...

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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
owner special
Owner special: Available start 3/15, 4703 3rd Ave, Holmes Beach, call cell or text message for details.

$360

avg/night

$360
avg per night
Owner special:
Available start 3/15, 4703 3rd Ave, Holmes Beach, call cell or text message for details.

View Details

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 5 BA | Sleeps 14 | Quick View
Sleeps 14, 5 bedrooms, 5 bathrooms
1 review

Distance to beach: 0.1 miles to Bayside Beach

$998

avg/night

$998
avg per night
View Details

Key Amenities

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

About this property

Just updated 2021, with state of the art finishes! 5 BR + 2 King Sleep Sofas, 1.5 Chaise Lounger, 5 BA Duplex can sleep many with direct views of Skyway Bridge and Tampa Bay in front and at canal end in back with frequent visits from Manatees!! Email owner about our other property that sleeps 6 for smaller ...

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Property Type

Anna Maria Island House

Featured review

"Family holiday"

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

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Anna Maria Island House
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom

Distance to beach: 45 feet to Gulf of Mexico

$512

avg/night

$512
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pet friendly
  • WiFi

About this property

Newly remodeled! Directly Across the Street from the Gulf of Mexico! 2 BR + Sleeper Sofa and 1.5 BA, + Outdoor Shower, fully stocked kitchen with bar, warm and inviting great room for family movie nights, second-level cottage.This beautiful cozy cottage home has everything you need to have a relaxing ...

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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
13 reviews

$2069

avg/night

$2,069
avg per night
View Details

Key Amenities

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

About this property

Welcome to paradise! This beachfront blends modernity with relaxation to give your group a heavenly experience. Located in a prime location on the North End of Anna Maria Island, Cloud 9 has everything that your group needs for a perfect vacation. Each of the 4 bedrooms is professionally decorated and ...

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Property Type

Anna Maria Island House

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

$1727

avg/night

$1,727
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 House
4 BR | 6 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 6 bathrooms

$3327

avg/night

$3,327
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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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

$425

avg/night

$425
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 House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
52 reviews

$1528

avg/night

$1,528
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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
44 reviews

$1312

avg/night

$1,312
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 | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3 bathrooms
53 reviews

$1223

avg/night

$1,223
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
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms
35 reviews

$1516

avg/night

$1,516
avg per night
View Details

Key Amenities

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

About this property

Beachfront paradise awaits you at the TripleTail.Located in a prime location - just one block from Pine Avenue and the City Pier, the 4 bed/4 bath bayfront home offers everything you need for the perfect vacation.On the ground floor, you’ll find a beachfront king bedroom, along with a ...

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Property Type

Anna Maria Island House

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

$543

avg/night

$543
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

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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

$942

avg/night

$942
avg per night
View Details

Key Amenities

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

About this property

Underwent complete INTERIOR REMODEL in Jan 2023!!! This Bean Point beauty is perfect for the family or group wanting to be ultra close & steps to one of the most beautiful sought after beaches in Florida! Aside from the fantastic location, this elevated 3 Bedroom 2 bath home has two amazing decks ...

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Property Type

Anna Maria Island House

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Anna Maria Island Vacation Rentals