Holmes Beach (Anna Maria Island, Florida) Vacation Rentals

(49 rentals)
Southern Comfort

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Southern Comfort is a private, single family home centrally located in Holmes Beach. This gorgeous 3 bedroom 2.5 bath vacation rental offers a private heated pool, front and rear balconies, gas BBQ grill, tropical landscaping, one car garage and much more! Just a brief 4 minute stroll to the pristine ...

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Property Type

Anna Maria Island House

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Starfish Cove

3 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

At 3 bedrooms and 2 full bathrooms, this is a beautiful choice for your next Anna Maria Island getaway! Two short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Cove is a luxurious and welcome retreat in ...

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Property Type

Anna Maria Island House

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Villa Del Mar

4 BR | 4 BA | Sleeps 10 | Quick View

$504

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

About this property

Cool and calming tiled floors, modern furnishings, and updated appliances give this vacation home an air of Tommy Bahama feel. We know how exhausting and stressful traveling can be so don’t feel an ounce of guilt if the second thing you do is plop down on the living room’s couch and switch ...

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Property Type

Anna Maria Island House

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Fantastic Beach View - Convenience & Comfort at Beach House for Family Fun.

$214

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

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 8 guests and is 150 feet from the ...

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Property Type

Anna Maria Island House

"Review of an Excellent Rental"
Reviewed April 19, 2019

The house is in a great location and is well equipped. Beach is only a few minutes away. The free trolley, which serves the entire island, is about a 5 minute walk.Supermarket and drug stores are nearby. ...

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Villa Verde

3 BR | 4 BA | Sleeps 6 | Quick View

$204

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

This Beautiful 3 bedroom 3.5 bathroom home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the private heated pool in your own backyard oasis. Villa Verde has every luxury you could want, the open concept floor plan is ...

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Property Type

Anna Maria Island House

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Beach Bliss

3 BR | 3 BA | Sleeps 6 | Quick View

$225

per night

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About this property

Incredible 3 Bed 3 Bath bungalow, Minutes From The Beach With Backyard OasisSpecial Rate does not include thanksgiving Christmas of New Years week This beautiful 3 bedroom 3 bathroom Bungalow is only minutes from the white sands beach of Anna Maria Island. Only a minute walk to the nearest free ...

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Property Type

Anna Maria Island House

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Paradise Beach House

6 BR | 6 BA | Sleeps 14 | Quick View

$449

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Kid Friendly
  • Pool
  • Private Pool

About this property

Stunning 6 bed 6.5 bath ~ Spectacular Pool & Spa ~ Walk to the beach and shops ***** IF YOU WOULD LIKE TO RENT FOR LESS THAN 7 DAYS PLEASE CONTACT US AT ***** Paradise Awaits Beach House ~ Be one of the first to enjoy this brand new 6 bedrooms, 6.5 bathrooms beach home that sleeps up to 14 and is ...

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Property Type

Anna Maria Island House

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Island Escape

4 BR | 5.5 BA | Sleeps 10 | Quick View

$599

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

ISLAND ESCAPE is the most beautiful house you'll find on AMI ~ brand new and simply FABULOUS! The photos just can’t show exactly how special this home really is. Be one of the first to bring their family and enjoy this home that features upscale, professional décor without a detail missed. ...

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Property Type

Anna Maria Island House

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Sea Salt

3 BR | 3 BA | Sleeps 6 | Quick View

$153

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

Sea Salt is a beautiful recently updated home home nestled in the heart of Holmes Beach-just a short 5 minute walk to the world renowned beaches of Anna Maria Island. This 3 bedroom 2.5 bath home offers everything you need for an unforgettable vacation. Enjoy the private heated pool with sand area, covered ...

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Property Type

Anna Maria Island House

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Starfish Isle

4 BR | 3 BA | Sleeps 10 | Quick View

$249

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. A few short blocks to the beach, and around the corner to restaurants, pubs & stores. Featuring a heated pool to relax in after your busy day, Starfish Isle is a luxurious and welcome retreat in the perfect location ...

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Property Type

Anna Maria Island House

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Conch Out Beach House

4 BR | 3 BA | Sleeps 10 | Quick View

$329

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

At 4 bedrooms and 3 full bathrooms, this is one of the best rentals on Anna Maria Island. Straight down the road 1 block to the beach, and around the corner to restaurants, pubs & stores. Featuring a huge heated pool to relax in after your busy day, Conch Out Beach House is a luxurious and welcome ...

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Property Type

Anna Maria Island House

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Anna Maria Paradise - Private Pool & Canal front home

$250

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool
  • Rentals by Owner

About this property

Beautiful 4 bedroom, 2.5 bathroom home with direct access to Anna Maria Canal and private heated pool overlooking the water. Take a kayak ride right off your private dock area or cast a fishing pole and catch dinner. This home has lots of space and is ready for you to come enjoy all of what the island ...

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Property Type

Anna Maria Island House

"Very nice"
Reviewed March 2, 2020

We met with the owner and he was very helpful in showing us around the property.The house was very clean and was everything we had expected. Brian and Marie

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A Hart of the Gulf

3 BR | 2 BA | Sleeps 6 | Quick View

$87

per night

View Details

Key Amenities

  • Air Conditioning

About this property

Quaint 3 bedroom, 2 bath private home in a quiet area of Holmes Beach only a short walk from the beach. A Hart of the Gulf is ground level and spacious with all the comforts of home included. Close to the free trolley, shops and restaurants. Accommodates up to 8 guests Amenities include: Linens, central ...

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Property Type

Anna Maria Island House

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Real Gulf-Front Beach House - One Step to the Beach!

$307

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Rentals by Owner

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 - with the best of both worlds - the sun and the shade.Beach and ...

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Property Type

Anna Maria Island House

"Simply the best!"
Reviewed December 29, 2019

We stayed at this lovely beach house over Christmas and it was everything we could ask for and more. You are ON THE BEACH with this fabulous location. The owners had a very well stocked home from beach ...

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Walker Beach Cottage

2 BR | 2 BA | Sleeps 4 | Quick View

1

$129

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

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

"Just what the Doctor ordered"
Reviewed October 7, 2019

This was the best vacation I have had in a few years. It was so easy to schedule - Libby the cottage manager was excellent and so accommodating. The cottage was charming, very clean, and well equipped ...

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Beach Vacation at Angelinos Sea Lodge on Anna Maria Island

1 BR | 1 BA | Sleeps 4 | Quick View

1

Distance to beach: 100 feet to Beach onsite

$150

per night

View Details

Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

Angelinos Sea Lodge offers four unique vacation rentals right on the beach of Florida Gulf Coast, Anna Maria Island, Holmes Beach. Hidden in a quiet residential street, these beachfront cottages are quaint, charming, and just a few steps to the white sand and blue sea. All beach cottages have direct ocean ...

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Property Type

Anna Maria Island Cottage

"Paradise on the Beach!!"
Reviewed March 6, 2020

The hosts are kind and accommodating and share their beautiful property generously! The unit was equipped with all necessary items for an enjoyable stay. The comfortable bed provided a great sleep after ...

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Gone Coastal: Beautiful Family & Pet-Friendly Home with a Heated Salt Water Pool

$171

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Private Pool

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 with ...

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Property Type

Anna Maria Island House

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Resting Beach Place

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Oceanfront
  • Pool

About this property

Don't miss out on the opportunity to stay steps away from one of the best beaches in Florida. This complex includes Tennis Court, Gazebo, Community Pool, Shuffle Board Court, Sauna, Pool Baths, Private ground level storage room, under building assigned parking, elevator, and garbage shoot. and laundry ...

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Property Type

Anna Maria Island Condo

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Gone Coastal Too: Beautiful Family & Pet-Friendly Private Home

$171

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pet Friendly
  • Private Pool

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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Costa Lotta

3 BR | 4 BA | Sleeps 8 | Quick View

$356

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

OverviewCosta Lotta is "home away from home”. All the amenities you will need in this 2100 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 ...

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Property Type

Anna Maria Island House

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Good Time and Tan Lines

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Don't miss the opportunity to one of the first to stay in this Stunning 3 bedroom 3 bathroom with bonus den area that has been completely renovated from bottom to top. This property is a new hidden gem of Holmes Beach.   The open concept floor plan is warm and inviting making you feel at home ...

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Property Type

Anna Maria Island Townhome

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Mermaid's Crossing

4 BR | 3 BA | Sleeps 10 | Quick View

1

$299

per night

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About this property

At 4 bedrooms and 3 full bathrooms, this is one of the most charming rentals on Anna Maria Island!! Located a few houses from the beach, it is only a two minute walk until white powdery sand is between your toes! Easy on the kids and even easier on you! Around the corner from restaurants, pubs & stores ...

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Property Type

Anna Maria Island House

"Yearly family vacation"
Reviewed May 20, 2019

Location was good with only a short walk to the beach and in a quiet location. House was clean and there was plenty of room for the group. Lots of pool and beach toys for us and the kids. The pool needed ...

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Seahorse Beach House

4 BR | 3 BA | Sleeps 8 | Quick View

$299

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen

About this property

202 81 st Street - Holmes Beach - Fl 34217 This Beautiful new 4 bedroom 3 bathroom home ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the heated pool in your own backyard oasis. This house has every luxury you could ...

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Property Type

Anna Maria Island House

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SO CLOSE to the Beach w/Heated Pool ~ Beach Please!

$139

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

ATTENTION: We offer 2 different units for rent. A total of 4 bedrooms are available and we can sleep up to 12 guests!For all the most up to date rates and availability please visit our main website. Click OWNER INFO and there you will find the links to each of our rentals. Thank you!Beach Please ...

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Property Type

Anna Maria Island House

"Perfect location"
Reviewed October 9, 2019

Julie was great to work with and responded very promptly to questions. The property was exactly as presented. The property was clean and inviting. Everyone in our party loved it. Additional information ...

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Peacock Place - Pet-friendly and very close to beach!

$271

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Update Friday, May 22, 2020: Manatee County submitted plan to State of Florida to allow vacation rentals and Florida DBPR approved! Beach is waiting for you!Update Saturday, May 2, 2020: Phase 1 of Re-open Florida begins Monday, May 4, but still no vacation rentals in Phase 1. Duration of Phase ...

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Property Type

Anna Maria Island House

"Family visit"
Reviewed July 3, 2019

Peacock Place is a great place for family reunions. Plenty of space. Close to the beach. We loved it.

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Salt Air East

2 BR | 2 BA | Sleeps 6 | Quick View

$199

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything!Salt Air East villa, located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island.Not in the mood for the beach? ...

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Property Type

Anna Maria Island House

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Crosswind Cottages

3 BR | 2.5 BA | Sleeps 8 | Quick View

$149

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

312 (B) 61st street - Holmes Beach - FL - 34217 Welcome to this luxury Key West style home by the sea! It is your place in the sun to make memories and unwind!Crosswinds Cottage is just a short five minute walk to Anna Maria Island's world renowned white sandy beaches where you will enjoy time with ...

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Property Type

Anna Maria Island House

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Turtle's Bay

3 BR | 3 BA | Sleeps 6 | Quick View

1

$279

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

"Beautiful Property"
Reviewed September 23, 2018

Visiting Anna Maria Island was amazing!! The weather was beautiful and the home was beautiful too!! I would definitely come back to visit this area.

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Summer Breeze

4 BR | 4 BA | Sleeps 10 | Quick View

$204

per night

View Details

Key Amenities

  • Air Conditioning
  • Pet Friendly
  • Private Pool

About this property

Overview 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 Queen Sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria ...

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Property Type

Anna Maria Island House

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Absolutely perfect

2 BR | 2 BA | Sleeps 4 | Quick View

2

Distance to beach: 0.5 miles to Manatee Beach

$105

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Rentals by Owner

About this property

Very contemporary condo (danish style), just refurnished and remodeled, and equipped with more than everything you need for a relaxing and unforgettable vacation in Paradise.The unit is inspiring and gives you a laid back feeling immediately after entering. A huge pool with lounges and sun umbrellas ...

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Property Type

Anna Maria Island Condo

"Fantastic stay!"
Reviewed July 22, 2018

The condo has everything you could possibly need. Carla and her husband were wonderful to work with, as was the local rental agency that managed the condo. We called for a minor issue - but they came ...

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307 65th Street

5 BR | 4 BA | Sleeps 10 | Quick View

2

$399

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Pool
  • Private Pool

About this property

This stunning brand newly built and decorated 5 bedroom 4 bath home is just steps from the sparkling white sandy beaches of the Gulf of Mexico. Located in prime Holmes Beach you are with in walking distance to the award winning Beach Bistro and many other restaurants, live music , bars and more. The ...

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Property Type

Anna Maria Island House

"Just Like Home!!!"
Reviewed December 22, 2019

This property is everything you see…we had a huge family (10) have an opportunity to stay at this beautiful property. Once you opened the door to walk in you immediately knew it wasn’t like other beach ...

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Dolphin Cottage - Pet-friendly and very close to beach!

$271

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Rentals by Owner

About this property

Update Friday, May 22, 2020: Manatee County submitted plan to State of Florida to allow vacation rentals and Florida DBPR approved! Beach is waiting for you!Update Saturday, May 2, 2020: Phase 1 of Re-open Florida begins Monday, May 4, but still no vacation rentals in Phase 1. Duration of Phase ...

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Property Type

Anna Maria Island House

"Love the Dolphin Cottage!"
Reviewed April 23, 2019

This is where you want to stay at the beach for a quiet old Florida experience. A beautiful beach is less than a block away where you can enjoy shade under the old Australian pines. The cottage is clean, ...

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Island Dream

3 BR | 2 BA | Sleeps 6 | Quick View

2

$158

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

About this property

Overview 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 ...

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Property Type

Anna Maria Island House

"GREAT POOL AND HOT TUB"
Reviewed August 13, 2019

We loved the Pool and Hot Tub. Home was well maintained and stocked with much of what we needed. A little further from the beach to walk, but close to many other restaurants,walking or driving.

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Gulf Sound - A

2 BR | 1 BA | Sleeps 6 | Quick View

$143

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OverviewGulf Sound is a gulf side, ground level tri-plex located on Gulf Drive in the southern end of Holmes Beach. Unit A at Gulf Sound is the southern unit. It is a two bedroom, one bath that will sleep six people. The unit has been updated and is comfortably furnished. It's quiet, yet close to ...

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Property Type

Anna Maria Island House

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Gone Coastal 3 Beautiful Family and Pet Friendly Home

$243

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool
  • Rentals by Owner

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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OCEAN 72

2 BR | 2 BA | Sleeps 6 | Quick View

$149

per night

View Details

About this property

Relax and unwind in this gorgeous, newly renovated 2 bedroom, 2 bath home close to everything!OCEAN 72, located only a short walk to the powdery white sandy beach of the Gulf of Mexico and ½ a mile from historic Pine Avenue on Anna Maria Island.Not in the mood for the beach? No Problem! ...

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Property Type

Anna Maria Island House

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Emerald Bay

3 BR | 3 BA | Sleeps 6 | Quick View

$279

per night

View Details

About this property

This brand new 3 bedroom 3.5 bathroom + den . This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. This house has every luxury you could want, Flat screen TV’s, ...

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Property Type

Anna Maria Island House

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Ocean View

6 BR | 5 BA | Sleeps 12 | Quick View

$449

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

OCEAN VIEW is a brand new construction home that features 6 bedrooms and 5.5 bathrooms and a fantastic location-just a 1 minute stroll to the White sandy beaches at the 65 th st access! This lovely property offers a private heated pool with a spa, water slide and grotto. The backyard is an oasis with ...

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Property Type

Anna Maria Island House

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Life's a Beach

2 BR | 2 BA | Sleeps 6 | Quick View

$122

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly

About this property

Life's a beach is a cozy, newly renovated 2 bedroom 1.5 bath home located in the heart of Holmes Beach. Being only a Short distance to the beach access means you can walk there with your morning coffee, or drink in hand to enjoy the spectacular evening sunsets! Life's a beach features a living room, dining ...

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Property Type

Anna Maria Island House

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SunSet Azul

2 BR | 1 BA | Sleeps 4 | Quick View

1

$146

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

OVERVIEWSunset Azul is a fully updated 2 bedroom 1 bath gulf side ground level villa on the southern end of Holmes Beach. This unit has been updated and is comfortably furnished. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the ...

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Property Type

Anna Maria Island Apartment

"Great stay at Sunset Vista as usual!"
Reviewed October 15, 2019

Went with my family 1st week of October. This is our second time staying at Sunset Vistas and we love it! We had wonderful weather and our room and view were great! We saw dolphins every morning. They maintain ...

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Caribbean Surf

3 BR | 2 BA | Sleeps 6 | Quick View

1

$169

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Private Pool

About this property

This beach 3 bedrooms 2 bathroom home is only a short stroll to the beautiful white sand beaches and miles away from any care. Covered deck looking over the pool is a wonderful spot to sit and relax or enjoy a meal. As they say, location is everything and this property is close to it all. 2 blocks ...

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Property Type

Anna Maria Island House

"Great home on Anna Maria Island"
Reviewed January 28, 2019

Beautiful home has everything thing you need. Wonderful heated pool my grandson loved the pool. Just a few blocks from the beach. Definitely would stay here again.

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Paradise Found

6 BR | 6 BA | Sleeps 12 | Quick View

1

$349

per night

View Details

About this property

401 42 nd Street - Holmes Beach - FL - 34217 This brand new 6 bedroom 6.5 bathroom - SLEEPS 14 Comfortably. This home is ideally located just down the street from the white sand beaches, restaurants and shops. After a day of fun in the sun relax by the salt water heated pool in your own backyard oasis. ...

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Property Type

Anna Maria Island House

"Awesome vacation house."
Reviewed November 2, 2019

Great house for vacation. 6 bedrooms and bathrooms. Nice pool and hot tub. Already had friends interested.

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Bare Feet Retreat

3 BR | 3 BA | Sleeps 6 | Quick View

$299

per night

View Details

Key Amenities

  • Full Kitchen

About this property

Stunning beach front resort with gated covered parking.

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Property Type

Anna Maria Island House

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Flip Flops Forever

5 BR | 3 BA | Sleeps 10 | Quick View

1

$184

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pet Friendly
  • Private Pool

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 4 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

"good location, across the street from the beach."
Reviewed March 25, 2019

Overall a wonderful experience. The beach is about a block from the house, close enough to not mind running back for bathroom or snacks. There are a few buckets and beach toys included, we left a few more. ...

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Kickback Cabana

3 BR | 2 BA | Sleeps 6 | Quick View

1

$229

per night

View Details

Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool
  • Private Pool

About this property

This large single-family home located in Holmes Beach on Anna Maria Island is the perfect spot to spend your next beach vacation. With 2 king bedrooms and a large 3rd bedroom with a queen bed and a single bunk bed, there is plenty of space for everyone. This home has just been completely repainted and ...

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Property Type

Anna Maria Island House

"Beautiful family-friendly house on Anna Maria Island"
Reviewed February 10, 2020

Beautifully decorated and well stocked, this house is within biking distance of the Pine Ave shops and an easy walk to the beach. The pool and spa were enjoyed by the whole family. Claire and Emma were ...

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Sits right on the beach! $139.99/night 2-week minimum and sorry no exceptions

$140

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Pool
  • Private Pool
  • Rentals by Owner

About this property

TWO WEEK MINIMUM STAY 2020 We have availability from July 29- September 24 and November 27th- December 31. 2021 Jan 1-Feb 1st Entire month April and May This gorgeous open concept, two bedroom, two bath, family room, dining area and kitchen was decorated by one of Florida’s top decorators ...

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Property Type

Anna Maria Island Condo

"Love Love Love this place"
Reviewed February 27, 2020

I've been coming to the island for 30 years and Tiffany Place is my favorite place on the Island. clean, convenient, beautifully decorated. It has all the conveniences of home. Beach chairs, grill and ...

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Anna Maria Island Condo~Close to the beach, shops & restaurants, heated pool!

$100

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Pool

About this property

Welcome to Paradise!When you come to Anna Maria Island for vacation, make this charming and inviting two-bedroom condo your home away from home! You're sure to love the relaxed island attitude with amenities like a heated pool, private screened lanai, and easy access to the beach, dining, and shopping. ...

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Property Type

Anna Maria Island Condo

"Stunning Accommodation"
Reviewed November 18, 2019

We arrived, looking forward to a three day trip to the island. We were delighted to find this beautiful apartment was situated in a lovely quiet area but close to the free trolley bus stop and Publix supermarket. ...

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Relax at The Ulmer House...Right on the Beach...Gulf Views Everywhere!

$307

per night

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Key Amenities

  • Air Conditioning
  • Beachfront
  • Full Kitchen
  • Oceanfront
  • Rentals by Owner

About this property

As you drive up to The Ulmer House, the landscape is natural, graceful and compliments the house in an authentic way. It feels like a compound from the street looking through the mature trees that surround a very large property and shield it from the view of the public. There is a very private and spacious ...

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Property Type

Anna Maria Island House

"wonderful home in a beautiful location!"
Reviewed July 23, 2019

This home was beautiful and had everything we needed for a wonderful week at the beach. The shaded lot and views of the beach from the house were outstanding!

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Songbird Cottage

2 BR | 1 BA | Sleeps 5 | Quick View

$70

per night

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Key Amenities

  • Air Conditioning
  • Full Kitchen
  • Kid Friendly
  • Rentals by Owner

About this property

Staying here amplifies the feeling of Anna Maria Island with that old Florida feel. Instant relaxation in a quiet neighborhood yet near most everything. There are several [ok so I like bikes and actually there are 8] that you can lazily bike through the neighborhood in the AM or evenings to take in all ...

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Property Type

Anna Maria Island Cottage

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Holmes Beach (Anna Maria Island, Florida) Vacation Rentals