Anna Maria Island Vacation Rentals

(236 rentals)
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Anna Maria Island Apartment
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 1 Bathroom

$255

avg/night

$255
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

Welcome to "Barefoot Mermaid 2" a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft, to white powder sand beaches of the Gulf of Mexico and less than a few flip flop ...

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Property Type

Anna Maria Island Apartment

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$296

avg/night

$296
avg per night
View Details

About this property

Welcome to Sea'Esta on gorgeous Anna Maria Island! Sea'Esta is a ground level Home that offers all the luxuries and comfort you will come to expect from staying at one of our vacation rentals on Anna Maria Island. This 2 Bed/2 Bath sweet and cozy beach home is located on North Shore Drive right ...

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Property Type

Anna Maria Island House

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Anna Maria Island Apartment
1 BR | 1 BA | Sleeps 3 | Quick View
Sleeps 3, 1 Bedroom, 1 Bathroom
1 review

$210

avg/night

$210
avg per night
View Details

Key Amenities

  • Air conditioning

About this property

Welcome to “Barefoot Mermaid 4” a relaxed ground floor vacation rental located on the north end of gorgeous Anna Maria Island. The serene location of this property is just amazing. Located steps, less than 50 ft to white powder sand beaches of the Gulf of Mexico and less than a few flip flop ...

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Property Type

Anna Maria Island Apartment

Featured review

"Perfect location."

Perfect 1-bedroom apartment, only a steps away from the beach! Perfect location within walking distance to everything on Pine Street.

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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

$263

avg/night

$263
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Oceanfront
  • Pet friendly
  • Pool
  • Private pool

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 House
4 BR | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 4 Bathrooms

$483

avg/night

$483
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool

About this property

*Under new owners, and new property management* Escape to this Anna Maria Island vacation rental “Katmandu” just 0.15 miles or 300 steps to the wonderful white sandy beaches of the Gulf of Mexico. This property is located west of Gulf drive, with no busy roads to cross for beach access. ...

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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
9 reviews

$177

avg/night

$177
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Smuggler’s Cove Resort is a family friendly timeshare property that offers studio and one-bedroom units. PLEASE INQUIRE AS TO AVAILABILITY OF UNIT TYPE, AS WE ARE UNABLE TO DELINEATE ON WEBSITE, THANKS! Each studio unit sleeps two with a queen-size bed and has a full kitchen. One-bedroom units ...

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Property Type

Anna Maria Island Condo

Featured review

"Great place to stay"

We recently stayed in one of the bay side units for vacation. This place is the best of both worlds. We had a view of water from our balcony but the private beach for the ocean was right across the road. ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
6 reviews

$427

avg/night

$427
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kitchen
  • Rentals by owner

About this property

Less than a minute's walk to the beach! Watch the sunset from the house! PARKING FOR ALL...Bring your boat or RV...Invite guests... There's room for everyone! Shell House is a two-story, 3-bed, 2-bath, multi-level fun-house on a large shady lot in a quiet residential neighborhood ...

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Property Type

Anna Maria Island House

Featured review

"Great Two Weeks in Holmes Beach"

I lived in Holmes Beach for many years. It was always my favorite place to be. When I needed to move I promised myself I would rent and come as often as I could. SunPlaza West has always been my go to ...

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Anna Maria Island House | On the beach
2 BR | 1.5 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 1.5 Bathrooms
11 reviews

$491

avg/night

$491
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • 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 - 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 Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
2 reviews

$156

avg/night

$156
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This spacious 2 bedroom condo is close to the beach and in the heart of it all. This stunning condo offers everything you want in a beach retreat. The unit has ample space your family. The open concept living area is perfect for entertaining, with a kitchen featuring all new appliances. You can also open ...

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Property Type

Anna Maria Island Condo

Featured review

"Great vacation rental!"

My husband and I rented this condo, Sand & Surf, from Owner, Morgan Henderson, and we were completely pleased with the accommodations. Morgan was wonderful about replying immediately to any questions we ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms
1 review

$476

avg/night

$476
avg per night
View Details

About this property

Treat yourself to “Crescent Palms” on the north end of Anna Maria Island. This ground level, newly renovated and professionally decorated 3 bedroom, 2 bath beach house offers comfort, luxury, and relaxation. Crescent Palms is located on a quiet street- north of Pine Ave and just a few flip ...

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Property Type

Anna Maria Island House

Featured review

"Peaceful and relaxing family trip"

We were looking for a quiet spot for the family and hit the bullseye at Max and Denise's place on Northern Anna Maria island. Centrally located, 3 blocks either way, between the Gulf of Mexico or Tampa ...

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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

Distance to beach: 0.1 miles to Beach Access 45th St

$427

avg/night

$427
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool
  • Rentals by owner

About this property

Address of Areca Cove: 206 N Harbor Drive, Holmes Beach, FL 34217 ARECA COVE - A bright and wonderful 4 bedroom/ 3.5 bath home just a 3-minute walk away from an astonishing white sand beach. With a heated pool in tropical and private surroundings, a covered patio by the pool area and multiple balconies ...

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Property Type

Anna Maria Island House

Featured review

"Perfect home and wonderful hosts!"

Olaf and Marissa were wonderful hosts - welcoming and responsive. Their home was absolutely perfect for a family get together with mixed ages. They have everything you need for a beach stay and the space ...

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Anna Maria Island Bungalow
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

310 60th street Unit B- Holmes Beach - 34217 To Book Directly please visit: /meant-to-bee If you are looking for something other than a 7 night stay, please give our office a call and we will do our very best to accommodate you! Beach Retreats Reservations Team: "You are vacationing in ...

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Property Type

Anna Maria Island Bungalow

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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
  • Kid friendly
  • Kitchen
  • 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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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

$415

avg/night

$415
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Pet friendly

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 Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
3 reviews

Key Amenities

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

About this property

This beachfront property is absolutely charming.! The unit offers a lovely 2 bedroom, 2 bath first floor walk out condo. Enjoy the open deck right to the sandy beach. Off the living room is a sliding glass door to the front deck. Inside you will find an open kitchen, a very classy living and dining room ...

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Property Type

Anna Maria Island Condo

Featured review

"Great stay during tropical storm Debby"

It's so amazing to step off your porch right onto the sand.. Oh the condo it's self was great too. Clean and beds were comfortable. Everything we needed was there. Tropical storm Debby hit and we still ...

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Anna Maria Island Cottage | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
31 reviews

$263

avg/night

$263
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation! Sailfish Gulf Suites is comprised of 4 separate suites. Suite 1 has direct views of the Gulf of Mexico and is just a few steps to the beach. It features 1 ...

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Property Type

Anna Maria Island Cottage

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Anna Maria Island Cottage
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
21 reviews

$192

avg/night

$192
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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

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 Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms
6 reviews

$211

avg/night

$211
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool
  • Rentals by owner

About this property

Click on calendar for available 2024 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS. TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry. 20 STEPS TO THE SAND - GREAT VIEW Last minute deals don’t last long, we price to rent. We are ...

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Property Type

Anna Maria Island Condo

Featured review

"Ok"

️ love this area one of my favorite places to stay AnnaMaria island.. love it .. can’t wait to go o back

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Anna Maria Island Cottage | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
20 reviews

$231

avg/night

$231
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation! Sailfish Gulf Suites is comprised of 4 separate suites. Suite 3 has garden views and is just a few steps to the beach. It features 1 bedroom with king size ...

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Property Type

Anna Maria Island Cottage

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Anna Maria Island Cottage | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
22 reviews

$231

avg/night

$231
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation! Sailfish Gulf Suites is comprised of 4 separate suites. Suite 4 has garden views and is just a few steps to the beach. It features 1 bedroom with king size ...

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Property Type

Anna Maria Island Cottage

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Anna Maria Island Condo | On the beach
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 Bedrooms, 2 Bathrooms

$352

avg/night

$352
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kitchen
  • Oceanfront
  • Pool
  • Private pool

About this property

The Beach Sands condo is completely surrounded by water with the Gulf of Mexico to the west, the Intra-Coastal Waterway to the east, Tampa Bay to the north and Sarasota Bay to the south. The Beach Sands offers the best location on Anna Maria Island where the island is only 150 yards wide. Our complex ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Cottage | On the beach
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 Bedroom, 1 Bathroom
29 reviews

$263

avg/night

$263
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen

About this property

Sailfish Gulf Suites is a Gulf front, Old Florida style ground level accommodation which guarantees your most memorable beach vacation! Sailfish Gulf Suites is comprised of 4 separate suites. Suite 2 has direct views of the Gulf of Mexico and is just a few steps to the beach. It features 1 ...

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Property Type

Anna Maria Island Cottage

Show less

Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

Key Amenities

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

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 House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Kitchen
  • Private pool
  • Rentals by owner

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

Featured review

"Perfect beach location with beautiful interior"

This duplex includes stunning beachy interior decorating, great location (quiet neighborhood with an easy walk to a white sands beach) with a bonus heated pool with outdoor shower, which was ideal after ...

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Anna Maria Island House
6 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 6 Bedrooms, 4.5 Bathrooms

$952

avg/night

$952
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool
  • Rentals by owner

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
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
5.0 rating on other travel sites

$342

avg/night

$342
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

If you are ready to put your "heels in the sand", look no further. Manna-Tee Beach House is the perfect vacation spot for relaxation on Anna Maria Island. This beautiful 3 bedroom/2.5 bath home located on Holmes Beach on Anna Maria Island has all the amenities for you. Top-of-the-line finishes ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 6.5 Bathrooms

$586

avg/night

$586
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

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 | 5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 5 Bathrooms
5.0 rating on other travel sites

$902

avg/night

$902
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Slice of Paradise VRC 216 68th St - Holmes Beach - FL - 34217 This stunning custom built and decorated 4 bedroom 5.5 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 ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$208

avg/night

$208
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Come relax and enjoy this stunning 2 bedroom/2 bathroom second level, recently updated condo at Runaway Bay. Runaway Bay is a bayfront complex that is less than a 1/2 block away from the beautiful beaches offering you all of the conveniences you would want in an island stay. The complex has a large heated ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms

$307

avg/night

$307
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

A picture is worth a thousand words, and you'll have plenty of photo-ops from your spacious, screened-in, second story balcony with unmatched up-close views of the ocean. Whether it's swimming in the shared heated pool or lying on the beautiful beach, there's no shortage of conveniences. ...

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Property Type

Anna Maria Island House

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Anna Maria Island Villa
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms

$387

avg/night

$387
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

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

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Property Type

Anna Maria Island Villa

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Anna Maria Island House
9 BR | 8.5 BA | Sleeps 8 | Quick View
Sleeps 8, 9 Bedrooms, 8.5 Bathrooms

$1028

avg/night

$1,028
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

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 | 4 BA | Sleeps 8 | Quick View
Sleeps 8, 4 Bedrooms, 4 Bathrooms

$1879

avg/night

$1,879
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

About this property

Private Beachfront Home - one block from Pine Avenue and the City Pier. Watch dolphins and manatees swim by from your back deck. Bike or take the golf cart (included) to explore the island and boutique shops and restaurants. Ground floor has a beachfront king bedroom with en-suite bathroom, second king ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2.5 Bathrooms

$393

avg/night

$393
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

This beautiful 2 bedroom/2.5 bathroom condo sits right on the beach. Exquisite views from your living room and primary bedroom. Located in Holmes Beach, the condo has a community pool and lounge chairs for you to relax and enjoy the sunshine. The floor plan is open and inviting with a sunken living room ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2 Bathrooms
4.9 rating on other travel sites

$301

avg/night

$301
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Beautiful 3 bedrooms/2 baths, plus den condo is in the highly sought out Bradenton Beach Club community. It has quality finishes including wood cabinets, solid granite surfaces, stainless steel appliances and quality tile in the living and bathroom areas. So well-appointed with comfortable furniture, ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 3 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 3 Bathrooms
1 review

$400

avg/night

$400
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pet friendly
  • Private pool

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
5 BR | 3 BA | Sleeps 10 | Quick View
Sleeps 10, 5 Bedrooms, 3 Bathrooms
2 reviews

$421

avg/night

$421
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • 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 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk (around 200 steps) ...

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Property Type

Anna Maria Island House

Featured review

"Perfect Beach House for just about anyone"

Love, Love, Love this beach house. I had reserved it a year in advance and was concerned about coming here during a pandemic but as soon as I arrived I was so happy and relieved to be here. The first ...

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Anna Maria Island House
3 BR | 2 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2 Bathrooms

$456

avg/night

$456
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Anna Maria Island House

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 Bedrooms, 2.5 Bathrooms

$363

avg/night

$363
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

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

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2 Bathrooms

$275

avg/night

$275
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen

About this property

Drive through the gated driveway with a manatee on it and you'll enter Manatee Retreat. This duplex is a private getaway on a canal! Unit B is separated by a fence so you have your own private retreat. This 2 bedroom/2 bathroom has a large living room with plenty of seating for you and your guests. ...

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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

$432

avg/night

$432
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Kai Blue is located in Holmes Beach, just steps from the beautiful AMI beaches. This 4 bedroom/2.5 bathroom with an elevator also has a private backyard with a pool. Kai Blue gives you the dreamy coastal vibe and it's close to restaurants, Island stores and right next to the free trolley stop. Pull ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 Bedrooms, 2.5 Bathrooms

$438

avg/night

$438
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Very few beachfront vacation homes will get you as close to the sand as Hidden Cove #1— a beautiful 2-bedroom condominium with exquisite views and unlimited access to the aquamarine Gulf of Mexico. Located within a charming coastal community that also offers a crystal-clear swimming pool, your family ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
5.0 rating on other travel sites

$437

avg/night

$437
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 23, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance Dream Weaver is an amazing, custom luxury home nestled in the quiet residential ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
4.7 rating on other travel sites

$208

avg/night

$208
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Run to the Sun is a 2 bedroom/2 bathroom updated condo located in the sought after Runaway Bay community and has breathtaking bay views. Everything you need to complete your ideal beach getaway, can be found at Runaway Bay! Runaway Bay is a Gulf to Bay complex that is less than a 1/2 block away from the ...

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Property Type

Anna Maria Island Condo

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

$772

avg/night

$772
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

Looking for a relaxing island retreat just steps from the soft white sand and turquoise waters in Bradenton Beach on Anna Maria Island? Look no further for your perfect vacation home for the whole family. Island Oasis is a custom-built spacious 8 bedroom/5 bathroom was professionally furnished to provide ...

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Property Type

Anna Maria Island House

Featured review

"Nice"

Very clean nice home enjoyed it...would consider renting again..thank you...talked with the owner and manager next door Great people

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 Bedrooms, 2.5 Bathrooms
1 review

$273

avg/night

$273
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Nestled in a tranquil coastal community in beautiful Holmes Beach, the aptly named Holmes Sweet Holmes is the ideal spot for your family's next escape to the shore. Featuring three blissful bedrooms and lots of communal living space, this picture-perfect home base allows everyone to have their own ...

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Property Type

Anna Maria Island House

Featured review

"Amazing time in Anna Maria island!"

We visited Anna Maria Island with the family and had a great time staying in this beautiful house.The property is spacious, nicely decorated, clean and very well equipped. It is nested in what seems to ...

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

$709

avg/night

$709
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

A 6-person electric golf cart is included with any new reservation for this property! You must be 21 years old and show proof of US driver's license and vehicle insurance. You'll fall in love with this incredible bay front 5 bedroom/6 full bathrooms home with a separate suite, having 2 full-size ...

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Property Type

Anna Maria Island House

Featured review

"Great getaway !"

A time much needed . We so enjoyed our stay at 2311 ave.c that we hope to return every year . We just felt like we were at home .

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Anna Maria Island Apartment | On the beach
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms

$334

avg/night

$334
avg per night
View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Kid friendly
  • Kitchen
  • Oceanfront
  • Pet friendly

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
7 BR | 6 BA | Sleeps 16 | Quick View
Sleeps 16, 7 Bedrooms, 6 Bathrooms

$831

avg/night

$831
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Private pool

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE BETWEEN ! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle Insurance. Endless Summer is the latest addition to SeaBreeze Vacation's portfolio. Pristine, newly ...

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Property Type

Anna Maria Island House

Show less

Anna Maria Island Condo
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 Bedrooms, 2 Bathrooms
1 review

$208

avg/night

$208
avg per night
View Details

Key Amenities

  • Air conditioning
  • Kid friendly
  • Kitchen
  • Pool

About this property

Lazy Days at Runaway Bay is the perfect place to take time out and relax at your home away from home. This ground floor beach condo has been updated and features a lovely open-floor plan, 2 bedrooms/2 bathrooms, as well as a sheltered lanai with views out to the lush tropical garden and is only steps ...

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Property Type

Anna Maria Island Condo

Featured review

"Fantastic area"

The condo and communications was perfect. NEVER had one issue. Would highly recommend. Clean pool and community activities.

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Anna Maria Island Vacation Rentals

Anna Maria Island Weather

 | 

7423°  5211°
JANUARY
Ocean 6518°
7624°  5412°
FEBRUARY
Ocean 6518°
7926°  5714°
MARCH
Ocean 6820°
8328°  6116°
APRIL
Ocean 7423°
8831°  6719°
MAY
Ocean 7926°
9133°  7222°
JUNE
Ocean 8328°
9133°  7323°
JULY
Ocean 8529°
9233°  7423°
AUGUST
Ocean 8731°
9032°  7323°
SEPTEMBER
Ocean 8529°
8630°  6719°
OCTOBER
Ocean 8228°
8127°  6016°
NOVEMBER
Ocean 7624°
7624°  5412°
DECEMBER
Ocean 7021°

Enjoy the Perfect Anna Maria Island Getaway


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

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

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

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

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

Anna Maria Island Travel Tips


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

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

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

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


Best Eats on Anna Maria Island


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

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

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

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


Things to Do Near Anna Maria Island Vacation Rentals


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

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

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

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

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

Experience Bliss on Anna Maria Island


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


FAQ

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

There are 236 Anna Maria Island vacation rentals available on FloridaRentals.com. From house rentals to condo rentals and beyond, find a unique vacation rental for you to enjoy a memorable vacation in Florida.

How much does it cost to rent a vacation rental in Anna Maria Island?

There are vacation rentals available in Anna Maria Island for as low as $127 per night with an average price per night of $390.

Can I find a vacation rental in Anna Maria Island?

Yes, you can find vacation rentals in Anna Maria Island close to Holmes Beach, Coquina Beach, and Bradenton Beach. Don't forget to stop in to Bean Point or Manatee Public Beach.

Do any vacation rentals in Anna Maria Island have a pool?

Yes, there are 117 vacation rentals with a pool in Anna Maria Island on FloridaRentals.com. Search using our filters and book one for your next vacation!

Are any Anna Maria Island vacation rentals on the ocean?

There are 17 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!