Pet Friendly Vacation Rentals in Anna Maria Island

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

Distance to beach: 0.1 miles to Bean Point

$882

avg/night

$882
avg per night
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Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience the peace and beauty of the North end of Anna Maria from this sprawling home named for its spectacular porches and outdoor space. *Features include* * Ultimate vacation home with elevator^ (currently out of service due to hurricanes, please inquire) * Private heated ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
4 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2 bathrooms
3 reviews

$519

avg/night

$519
avg per night
View Details

Key Amenities

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

About this property

Longing for an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay ...

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Property Type

Anna Maria Island Condo

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

$748

avg/night

$748
avg per night
View Details

Key Amenities

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

About this property

Welcome to Zen Gardens on beautiful AMI. BIG NEWS: a brand new, full sized pool and spa was installed and is ready for your use. Zen Gardens is located just north of Pine Ave - and 1 house from the beach - in the City of Anna Maria. This property offers a beachy bohemian vibe and has all you need for ...

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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
2 reviews

$563

avg/night

$563
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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Property Type

Anna Maria Island House

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Anna Maria Island Condo | On the beach
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms

$358

avg/night

$358
avg per night
View Details

Key Amenities

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

About this property

Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2 bedroom 2 bathroom Condo is located in the heart of Holmes Beach within walking distance to restaurants, shopping and the Islands Free Trolley. Sun Plaza West complex offers a secure entry, an elevator, heated pool and ...

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Property Type

Anna Maria Island Condo

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

$409

avg/night

$409
avg per night
View Details

Key Amenities

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

About this property

Dreaming of an island vacation? This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Step outside your door and find our beautiful beaches; many local eateries; FREE rides on the Island trolley; unique boutique shopping or you can stay on site ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Cottage
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
49 reviews

$249

avg/night

$249
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Condo-cottage with Old Florida charm..... Welcome to paradise.....This updated cottage is within a small resort, just steps from a beautiful private gulf beach. Drive into the Tradewinds Resort, and you will find quaint, pastel colored cottages on both sides of you hidden behind lush tropical foliage. ...

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Property Type

Anna Maria Island Cottage

Featured review

"AMI Tradewinds Resort"

Stayed at Tradewinds Resort located at 1603 Gulf Rd and what a beautiful cozy place. One bedroom, with a pullout couch in the living room (overall can easily fit 4). Kitchen and dining area was roomy. ...

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

$278

avg/night

$278
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

Relax with the whole family at this peaceful place to stay. Endless Summer is two bedroom, two bath condo located on Anna Maria Island. Specifically, located in Runaway Bay on Bradenton Beach. We have beach wagon. umbrella, chairs and cooler for your use. This unit is ground level, no stairs! Endless ...

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Property Type

Anna Maria Island Condo

Featured review

"Great Place, Perfect Location"

My husband and I recently stayed at this condo while visiting family and friends. This was the perfect condo and perfect location for us. Unfortunately, the pool was down for repairs of some sort but we ...

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Anna Maria Island House | On the beach
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

$778

avg/night

$778
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 Apartment | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms

$459

avg/night

$459
avg per night
View Details

Key Amenities

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

About this property

Unwind in this beachfront retreat! Just steps from the sand, this modern 2BR/2BA condo boasts stunning ocean views. Relax on the cozy turf patio with smart TVs and high-speed WiFi. The fully equipped kitchen is perfect for meals, and 2 dedicated parking spots add convenience. Unique touches: Unwind ...

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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 10 | Quick View
Sleeps 10, 5 bedrooms, 4.5 bathrooms
5 reviews

$814

avg/night

$814
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island! As you step through the front door, you enter a bright and ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
6 BR | 5.5 BA | Sleeps 14 | Quick View
Sleeps 14, 6 bedrooms, 5.5 bathrooms
14 reviews

$1319

avg/night

$1,319
avg per night
View Details

Key Amenities

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

About this property

ASK US ABOUT MULTI WEEK DISCOUNTS!! Featuring 6 bedrooms 5.5 baths (sleeps 14) and a fantastic location - just a 1 minute walk to the white sands of the 65th St Beach Access! This vacation home offers a huge heated pool with spa, rock water slide and grotto waterfall. Covered outdoor entertaining ...

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Property Type

Anna Maria Island House

Featured review

"Perfect!"

This place was perfect for our family! The 4 bedrooms with King size beds and en suite baths made it so convenient for each couple. The bunk beds were perfect for the kids. The children (and adults) loved ...

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

$880

avg/night

$880
avg per night
View Details

Key Amenities

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

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 150 five-star ratings from Airbnb/VRBO! Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated ...

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Property Type

Anna Maria Island House

Featured review

"Hidden paradise"

We were attending a beach wedding and made a vacation out if it. I connected with the owner Kath immediately. She was generous, attentive, available and without a doubt the best host we have ever met. ...

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

$729

avg/night

$729
avg per night
View Details

Key Amenities

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

About this property

Welcome to “Pineapple Cottage” – a beautifully updated ground level beach cottage located in the heart of Anna Maria City and just 1 block from all the shops, restaurants and fun on Pine Avenue. This charming cottage has been professionally decorated and offers all the luxuries you will ...

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Property Type

Anna Maria Island House

Featured review

"Great Property"

This house is in a great location, three blocks to the beach, restaurants, and three blocks to the pier, and many other amenities. It is beautiful, spacious and has everything you need to make your stay ...

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Anna Maria Island House | On the beach
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$351

avg/night

$351
avg per night
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 | On the beach
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
12 reviews

$351

avg/night

$351
avg per night
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

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 | On the beach
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
  • 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
1 review

Distance to beach: 0.1 miles to Tampa Bay

$1022

avg/night

$1,022
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Views, views, views! Experience all the best of the North end of Anna Maria from this waterfront home with pool and mini golf. *Features include* * Ultimate Bay front vacation home * Private heated pool and full Putt-putt course * Paddleboards, kayak * Gas grill and outdoor dining * Huge ...

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Property Type

Anna Maria Island House

Featured review

"Sandtrap house with Beach Boutique"

Beautiful home, fantastic location and incredible service. Everything was perfect. Live the area, restaurants, biking, atmosphere and people. Super friendly. We will be back using Beach Boutique again!

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Anna Maria Island House | On the beach
3 BR | 2 BA | Sleeps 10 | Quick View
Sleeps 10, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

The Salty Mermaid Team is excited to introduce our newest property, The Haven Unit 1 and Unit 2! *This property requires a 7-night minimum stay. Arrival and departure days must fall on a Saturday* When booking this listing, you will be reserving both Units at this Duplex. Haverkos on Holmes- ...

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Property Type

Anna Maria Island House

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

$292

avg/night

$292
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Vacations can be exciting and so overwhelming. Don’t worry, we’re here to help. Pack your bags and get ready to enjoy our beautiful island. This unit with its PRIVATE entrance is part of a 3 unit complex. These units only share pool and grilling area. Just steps outside your door you will ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House | On the beach
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

$933

avg/night

$933
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
3 BR | 3 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Welcome to Gone Coastal 3! This quaint three bedroom, two bathrooms plus a half bath vacation home is located just a short walk from Anna Maria Island’s sugar white sands and crystal clear waters! Beach towels, six beach chairs, and a beach wagon are provided to ensure your days spent in the sun ...

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Property Type

Anna Maria Island House

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

Key Amenities

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

About this property

Centrally located in Holmes Beach, this elevated two bedroom/two bath half duplex has its own private heated salt water pool and outdoor bbq area! It also has an outside shower for showering off after your trips to the beach. Inside it has a split plan with a king sized bedroom and a second bedroom ...

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Property Type

Anna Maria Island House

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

$269

avg/night

$269
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • Pool
  • WiFi

About this property

*** SPECIAL *** Book a 14 day stay and ONLY pay for 12 Buckeye Haven s situated in one of the sought after community of Playa Encantada! Come enjoy this tropical beach front community on the white sandy beaches of Anna Maria Island! This popular destination is sure to please beach goers, as well as ...

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Property Type

Anna Maria Island Condo

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

Distance to beach: 45 feet to Gulf of Mexico

$507

avg/night

$507
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
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms

$648

avg/night

$648
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

North End Escape is a 2,300 sq. ft. Custom Built 3 bedroom 2 ½ bathroom Home featuring a 400 sq. ft. Rooftop Covered Gazebo; 750 sq. ft. of Covered Outdoor Living Area with Travertine flooring and a Heated Pool. This spacious home has wide plank hardwood flooring throughout; open concept living ...

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Property Type

Anna Maria Island House

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Anna Maria Island Cottage
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2 bathrooms
21 reviews

$227

avg/night

$227
avg per night
View Details

Key Amenities

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

About this property

My wood-frame beach cottage was built in 1936, and was originally part of 6-8 cottages and a lodge house. It is the only surviving cottage, many having been taken by hurricanes. (Forward of the cottage’s beach, a street and an entire city block of the old subdivision are submerged beneath the ...

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Property Type

Anna Maria Island Cottage

Featured review

"Old Florida Gem"

Loved the old Florida vibe! A hop and skip to the beach - just what we were looking forward to! Sure beats a condo high rise!

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

$581

avg/night

$581
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Moon Shadow South's location can't be beat with views of Passage Key in Tampa Bay from the Primary Ensuite. You are just steps away to the bay beach access located directly across the street; walking distance to the Rod and Reel Pier, Bay Front Park and the popular white sandy beach of Bean ...

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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

$1151

avg/night

$1,151
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.9 rating on other travel sites

$426

avg/night

$426
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 | 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

$737

avg/night

$737
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
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 Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
1 review

$246

avg/night

$246
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
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

$318

avg/night

$318
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

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

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Property Type

Anna Maria Island House

Featured review

"GREAT LOCATION"

Great location in middle of Ana Marie Island; close to beach, not to far to shopping and restaurants. Rum Dog is a clean two bedroom pet friendly unit with wonderful deck for eating and socializing Rental ...

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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

$884

avg/night

$884
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
4 BR | 3.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 3.5 bathrooms
1 review

$553

avg/night

$553
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 | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$1291

avg/night

$1,291
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

About this property

Gulf Beach Front 3 bedroom/3 bathroom home and separate 1/1 cottage Sunset's from your back deck and morning shell searches out your back door. All bedrooms are King Bed en-suite. Located on the North End of Anna Maria Island. Gas BBQ on the lower deck. TV are located in all bedrooms. Plenty of space ...

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Property Type

Anna Maria Island House

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

$978

avg/night

$978
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Large 4 bedroom/2 bathroom Ocean view home with screened porches in the front and back. Elevator to the main level. Beach is right across the street. Bikes, Paddle Boards and a golf cart included. We are pet friendly! Pre-approved pet's , a signed pet agreement and pet fee paid in full will be needed. ...

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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

$1281

avg/night

$1,281
avg per night
View Details

Key Amenities

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

About this property

128 49th St Holmes Beach VRC 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 time, or for reservations made on or less ...

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Property Type

Anna Maria Island House

Featured review

"Great Thanksgiving Vacation!"

We spent Thanksgiving week at Sunset and Sand and it delivered on all our expectations. The home is clean, beautifully decorated and functional. The kids absolutely loved the heated pool and Spa and Its ...

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

$582

avg/night

$582
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 House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4 bathrooms

$1759

avg/night

$1,759
avg per night
View Details

Key Amenities

  • Pet friendly
  • WiFi

About this property

Mintfish is a tropical hideaway that blends high-end decor with natural beauty. This 4 bedroom, 4 bath ground-level luxury vacation home has recently been remodeled to combine natural and sustainable materials with decadent living. The single-floor layout makes the home easily accessible to people of ...

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Property Type

Anna Maria Island House

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

$1252

avg/night

$1,252
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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

$1551

avg/night

$1,551
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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

$859

avg/night

$859
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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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

$1240

avg/night

$1,240
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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 to ...

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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

$2550

avg/night

$2,550
avg per night
View Details

Key Amenities

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

About this property

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

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Property Type

Anna Maria Island House

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

$1932

avg/night

$1,932
avg per night
View Details

Key Amenities

  • Air conditioning
  • 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
8 BR | 6.5 BA | Sleeps 18 | Quick View
Sleeps 18, 8 bedrooms, 6.5 bathrooms
1 review

$2465

avg/night

$2,465
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
2 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 2 bedrooms, 4 bathrooms

$2075

avg/night

$2,075
avg per night
View Details

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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Property Type

Anna Maria Island House

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

$1246

avg/night

$1,246
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 Vacation Rentals