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Anna Maria Island Vacation Rentals

(280 rentals)
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Aqua Blu is a newly remodeled 2 bedroom/2 bathroom gulf front condo that offers everything you will need for a carefree getaway including a heated community pool and spa. From the moment you walk in, you are welcomed by stunning gulf views. Your private balcony will be the perfect resting place both day...

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$451
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • 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 completely restored after hurricanes Helene and Milton. This...

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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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$734
avg per night
Anna Maria Island Townhome
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Welcome to Island Retreat where you can enjoy the tranquility of listening to waves, watching dolphins, coastal birds and sunsets you'll remember for the rest of your life. This beautifully remodeled 1 bedroom/1 bathroom condo has everything you will need to make everlasting memories of adventure...

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Featured review

"close to white sandy beach"

Everything you would need for a beach vacation. The beach front cafe had live entertainment nightly, a perfect place for sunsets.

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$189
avg per night
Anna Maria Island Cottage
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Great place!"

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

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$449
avg per night
Anna Maria Island Townhome
Sleeps 6, 2 bedrooms, 2.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

Crisp, clean, and completely remodeled— this 2 bedroom townhome is the perfect spot to make unforgettable Anna Maria Island memories. The warm sand and turquoise water of the Gulf of Mexico are right across the street. You'll be steps away from the beach and a quick stroll or bike ride from...

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Featured review

"Great for families!"

Great unit, excellent communication, comfortable beds! Kids utensils, pool/beach toys, pack n play, and toddler bed rail all there!

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$312
avg per night

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Anna Maria Island House
Sleeps 8, 4 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Casa Del Mar is a beautiful Key West-style home featuring 4 bedrooms/2.5 bathrooms. This property is located on the north end of Holmes Beach close to shopping, restaurants and trolley stops. Best of all, this unit is within walking distance to the white sandy beaches. Amenities also include heated pool,...

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Featured review

"74th Street"

This is a great place to stay! Easy walk to the beach. Super nice rental. Seabreeze was responsive to all questions and concerns.

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$369
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

NEWLY RENOVATED! Going Coastal is a 2 bedroom/2 bathroom home located on the north end of Anna Maria Island. This ground level canal front home has everything you need to make this your best Anna Maria Island vacation ever. This home offers a private heated pool overlooking the mangroves and canal, private...

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$465
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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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$477
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .This cozy beach condo has been updated and features a lovely open floor plan,...

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$251
avg per night
New
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Please note that surrounding units may still be undergoing improvements. The shuffleboard, club house, and fitness center are currently unavailable until further notice. For updates, please contact SeaBreeze Vacation at .Recently Renovated!Welcome to your perfect beach retreat! This beautifully...

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$289
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

306 Clark drive (B) Holmes Beach, FL 34217 VRC Dog Friendly! Beautiful open concept home. 3 king bedrooms with en suites and a den with 2 single bunk beds make this property perfect for multi-generational or multi-family vacations. This home is ideally located just down the street from the white sand...

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Featured review

"Beautiful Property"

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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$418
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Conch-Out Beach House 303 68th St, Holmes Beach, FL 34217 VRC | 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool + Spa | Pet-Friendly Completely Renovated February 2025! Welcome to Conch-Out Beach House, a beautifully renovated one-level bungalow that blends classic Florida charm with modern...

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Featured review

"Beautiful house with a very short walk to the Gulf beach."

This is a great house in a fantastic location. The close beach access is very convenient. There are 6 complimentary high quality beach chairs that came in very handy. There is even a handy beach wagon...

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$329
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Angel Sea by Beach Retreats Vacation Rentals VRC 4118 5th Ave, Holmes Beach, FL 34217 6 Bedrooms | 3.5 Bathrooms | Sleeps 12 | Elevator | Heated Pool & Hot TubWelcome to Angel Sea—a stunning 6-bedroom, 3.5-bathroom vacation home designed for family gatherings and group getaways on Anna...

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Featured review

"Family vacation"

House was very comfortable. Everything was as advertised. Pool heater was not working when we checked in. They offered us the use of the pool next door. It was very kind and made our trip perfect.

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$441
avg per night
Anna Maria Island Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

202 81 st Street - Holmes Beach - Fl 34217 VRC Book with confidence: NO CANCELATION FEES Cancellation Policy (Effective for reservations made on or after August 13, 2025) $500 deposit due at time of booking; balance due 30 days prior to arrival Cancel 60+ days before arrival → Full refund (no...

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Featured review

"Pleased"

We enjoyed our stay. The access to the beach and other amenities was perfect for our family. The rental was very clean and well kept. Most everything you needed for the stay was available. The pool was...

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$323
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

VRC 107 78th street Holmes Beach 34217 “You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property”️...

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$153
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

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

About this property

Luxury 4-Bedroom Island Getaway with Pool & Spa – Steps from Holmes Beach!Welcome to your dream vacation home! This custom-built 4-bedroom, 4.5-bath home offers everything you need for an unforgettable Anna Maria Island escape . Designed with no expense spared, this luxurious retreat features...

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$463
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Surf Side Beach House – Gulf Views Hosted by Beach Retreats Vacation Rentals 6605 Gulf Drive, Holmes Beach, FL 34217 VRC19-00290Welcome to Surf Side Beach House, a stunning custom home located right across the street from the beach! ️ Enjoy beautiful Gulf views and an unbeatable island...

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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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$772
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

306 67th Street Unit B Holmes Beach, FL 34217 VRC Caribbean Surf by Beach Retreats Vacation RentalsHolmes Beach, Anna Maria Island 3 Bedrooms | 2 Bathrooms | Sleeps 6 | Private Heated Pool | Pet-FriendlyYour Anna Maria Island Bungalow Retreat Welcome to Caribbean Surf, a bright and inviting...

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Featured review

"Nice Little property!"

The home has recently been redone, very comfortable and accomodating with a nice sitting deck and new pool. We had a short walk to a beach access and the location allowed us to visit the north island area...

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$239
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

114 48th Street Holmes Beach, FL 34217This absolutely gorgeous 4 bedrooms 3 bathroom home is located in the heart of Anna Maria Island in Holmes beach. It is only a short stroll to the beautiful Gulf Beaches. With a 2 car garage an extra-large driveway there is more than enough guest parking. Take...

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$499
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Island Escape by Beach Retreats Vacation Rentals 307 65th St, Holmes Beach, FL 34217 VRC Your dream getaway awaits on Anna Maria Island! This stunning 4-bedroom (+ bonus room), 4-bath luxury vacation home is just steps from the beach and close to the best dining, shopping, and island attractions....

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Featured review

"Pleasantly surprised"

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

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$455
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Crosswind Cottage312 A 61st Street, Holmes Beach, FL 34217 VRC | 3 Bedrooms | 2.5 Bathrooms | Sleeps 10 | Heated Pool | Game Room | ElevatorWelcome to Crosswind Cottage, a spacious island retreat designed for comfort, fun, and relaxation. With three king bedrooms, a private pool, game room,...

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$256
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

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

About this property

Just Beachy – Your Luxury Island Retreat on Anna Maria IslandEscape to Just Beachy, a beautifully appointed 4-bedroom, 5.5-bathroom luxury home just a short walk from the crystal-clear waters ️ and powder-soft sands of Holmes Beach. Thoughtfully designed for comfort, style, and convenience,...

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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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$582
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 3 bathrooms
2 reviews

Key Amenities

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

About this property

Beach Bliss by Beach Retreats Vacation Rentals 320 64th Street, Holmes Beach, FL 34217 3 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub | Walk to Beach | Pet-Friendly Fully Renovated February 2025 Welcome to Beach Bliss, a beautifully updated 3-bedroom, 3-bathroom bungalow just...

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Featured review

"Girls weekend"

Outside patio was perfect! The pool and hot tub were great. Living room area was small but comfortable.

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$256
avg per night
Anna Maria Island Townhome
Sleeps 10, 5 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

202 69 th Street - Holmes Beach - FL 34217 VRCBook with confidence: No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking;...

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Featured review

"Lovely stay"

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

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$426
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
2 reviews

Key Amenities

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

About this property

411 79th Street Holmes Beach, Fl 34217 VRC No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60 days prior Third-party...

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Featured review

"Nice Getaway"

We really enjoyed this vacation rental home. Excellent location with close proximity to the beach and restaurants. Also, house located on a quiet street. Amenities were great including the pool and the...

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$308
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

302 60th Street Holmes Beach, FL 34217 VRC 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...

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Featured review

"The perfect oasis"

My husband and I had the best time at the home we rented on Anna Maria Island. It was spacious and we had far more room than we needed for just the two of us. When we arrived, everything was clean and easy...

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$220
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Pool
  • WiFi

About this property

VRC 107 78th street Holmes Beach 34217To Book Directly please visit: /chasing-wavesIf 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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Featured review

"Great Location and Clean"

We had a great week in this unit and were pleased with many things it had. I would stay there again without hesitation. A FEW issues though with the unit. A fee of $69 for linens. We rented for 10 days...

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Anna Maria Island Townhome
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

VRC 21 Holmes Blvd Holmes Beach, FL 34217 At 4 bedrooms and 3 full bathrooms, this is a great option for one or two families to stay at. 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...

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Featured review

"Wonderful, Clean home with pool!"

The home was absolutely wonderful with everything we needed to make our weeklong vacation a success! Everything was clean and well kept. The beds were comfortable and the best part was the pool and pool...

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$308
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

The elevator at Bradenton Beach Club is currently not operational due to a licensing issue. For updates, please contact SeaBreeze Vacation at .Beautiful 3 bedrooms/2 baths condo is in the highly sought out Bradenton Beach Club community. It has quality finishes including wood cabinets, solid granite...

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$280
avg per night
Anna Maria Island House
Sleeps 12, 6 bedrooms, 6.5 bathrooms
2 reviews

Key Amenities

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

About this property

401 42nd Street Holmes Beach, FL 34217 VRCNo cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60 days prior Third-party...

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Featured review

"Paradise Found"

We rented this home for time with our kids and grandkids. It worked great! The rooms were spacious and it was great that every room had a bathroom. We had no issues. The kitchen was well stocked. The backyard...

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$467
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS! All Drivers must be over the age of 21. Drivers must provide valid Driver's License and Vehicle Insurance. To drive the golf cart, non-US driver license holders are required to pay an additional $25 per day instead of providing vehicle insurance....

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$393
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 6.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Paradise Beach House – Luxury 5-Bedroom Retreat with Pool & Jacuzzi403 42nd Street, Holmes Beach, FL 34217 | VRCWelcome to Paradise Beach House, a stunning 5-bedroom + bonus bunk room, 6.5-bathroom luxury retreat just a 5-minute walk from the pristine shores of Holmes Beach ️. Perfect...

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$467
avg per night
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

The elevator at Bradenton Beach Club is currently not operational due to a licensing issue. For updates, please contact SeaBreeze Vacation at . ​​​​​​​ Bradenton Beach Club is a beautiful Gulf to Bay property that is 1/2 a block away from the sandy white beaches offering you all of the...

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$173
avg per night
Anna Maria Island Townhome
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

Key Amenities

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

About this property

Emerald Bay 306A Clark Street, Holmes Beach, FL 34217 VRC | 3 Bedrooms | 3.5 Bathrooms | Sleeps 6 | Heated Pool & Spa Welcome to Emerald Bay, a luxury coastal retreat just a 5-minute stroll from the white sand beaches of Anna Maria Island. With three king bedrooms, a private heated pool &...

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Featured review

"Relaxing Getaway"

This was our perfect getaway. The house is beautifully decorated inspired by the blue glistening water and white sandy beaches of Ana Maria Island. The kitchen was fully equipped with everything we needed...

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$308
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

210 65th Street Holmes Beach, FL 34216 VRC No cancellation fees! Cancel 60+ days before arrival → Full refund Cancel within 60 days → No refund Extended stays & bookings $20,000+ → Full payment 90 days prior, non-refundable $500 deposit due at booking; balance due 60 days prior Third-party...

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Featured review

"Yearly family vacation"

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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$370
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 0.5 miles to Manatee Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bed/2bath condo on second floor, fits up to four guests, close to the gulf beach. Turnkey furnished and spruced by the owner. Shops and restaurants are close by. Trolley stop for free rides on the island is around the corner. Come and enjoy!Just remodeled and equipped with more than everything...

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Featured review

"Fabulous stay on Anna Maria Island"

This condo was the PERFECT place for our family of three to enjoy Anna Maria Island! It was clean, cozy, and had everything we needed! Carla was a wonderful host who was very accommodating and gracious...

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$241
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Welcome to Villas by the Sea 4! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Heated Community Pool Fully stocked kitchen for all of your...

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$270
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 5.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Located in the heart of Holmes Beach on Anna Maria Island, this 4-bedroom, 5.5-bath coastal getaway is your dream vacation home — perfect for families, friends, or group trips.️ Short walk to the beach Private mini putt-putt + game room Heated pool + spa oasis Close to bars, dining,...

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$926
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to Hammock Hideaway! .02 Miles to Pine Ave. Shopping, Restaurants, and more! .03 Miles to AMI Beaches Private Heated Pool, BBQ Grill, Sun Loungers Beach chairs, wagon, and a cooler available Family friendly with pack'n'play and highchair High-speed Wi-Fi, Smart lock for Self-Check-in,...

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$986
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

NOTE - The pool will be closed for resurfacing starting in Mid July through the beginning of September.Welcome to Sun Plaza West 101! *Highlighted Amenities** Location! Gulf Front Resort Condo Community! * 2 Bedrooms / 2 Bathrooms * 1 King Bed & 2 Twin Beds (Or can make 1 King upon request) *...

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$337
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 1 bathroom
4 reviews

Distance to beach: 0.3 miles to Anna Maria Bay Front part

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

Newly renovated with a modern European Interior designer for comfort, beauty and relaxation at its best.Million-dollar views with fantastic and serene sunsets and nature watching Best island location - north – and just at the end of Pine Avenue with walking distance to the City Pier, shops,...

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Featured review

"Beautiful Property"

This property is located in a beautiful area! Very quiet and comfortable. Nice and clean…I highly recommend this property to anyone! You won’t regret it .

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$451
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Distance to beach: 50 feet to across the street

Key Amenities

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

About this property

Key Lime Cottage – 880 N Shore Drive, Anna Maria Island3 Bedrooms | 2 Bathrooms | Sleeps 8 | Pet Friendly | Private Hot Tub | Fenced BackyardWelcome to Key Lime Cottage, a charming slice of island life nestled along the coveted North Shore Drive on Anna Maria Island. With room for up to...

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$798
avg per night
Anna Maria Island House
Sleeps 8, 5 bedrooms, 5 bathrooms

Key Amenities

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

About this property

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

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$2,425
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Mermaid Sunset! Private Heated Pool/ Spa 200 steps to Holmes Beach Beach Chairs & Wagon Available for use 1 Mile to Pine Ave. Fishing, Shopping, Restaurants, and more High speed Wi-Fi, Smart lock for Self Check-in Pool Heat included with rental Welcome to Mermaid Sunset! This...

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$424
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

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

About this property

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

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$1,980
avg per night
New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Welcome to Flamingo Fling by Coastal Chic Vacations!- Steps to Anna Maria Island's white sandy beaches - Private heated pool - Hot tub - Private putting green - 4 spacious bedrooms & 3 bathrooms - Ground level home - Close proximity to local dining, grocery store, shops... - Beach...

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$619
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Pool
  • WiFi

About this property

Welcome to Villas by the Sea 5! .01 Miles to the World Class Beaches of Anna Maria Island .02 Miles to Bridge Street Pickleball Courts & Playground Across the Street Beach Wagon, Chairs, Umbrella, & Cooler available for use Fully stocked kitchen for all of your favorite home cooked...

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$322
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Hidden Treasure Unit A! .1 Miles to Holmes Beach Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Fully stocked kitchen for all your favorite home-cooked meals Shared Heated Pool High-speed Wi-Fi included Smart lock for Self Check-inWelcome...

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$376
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Pet friendly
  • Pool
  • Rentals by owner
  • WiFi

About this property

2 bedroom 2 bath 1000 square feet condo with a beachfront view of the Gulf of Mexico on the quiet, peaceful Anna Maria Island. Walking distance to many restaurants and bars. 30 minutes away from the Sarasota/Bradenton airport. Free trolley to go anywhere on the island.

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Featured review

"Big Joe"

Awesome unit with great views and access to the beach as well as restaurants and grocery stores. I would definitely stay there again. Great time and relaxing vacation.

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$127
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Welcome to paradise on beautiful Anna Maria Island! Sunbow Bay 209 is a newly furnished 2 bedroom 2 bath condo with new appliances and coastal decor overlooking a peaceful serene lagoon with kayak and canoe access directly to the intercoastal waterway.Enjoy stunning sunrises with a cup of coffee on...

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$218
avg per night
Full map
Map

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°

FAQ

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

There are 280 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 $411.

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 203 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 22 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!