Holmes Beach (Anna Maria Island, Florida) Vacation Rentals

(94 rentals)
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Anna Maria Island Condo
2 BR | 2.5 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 2.5 bathrooms

$627

avg/night

$627
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Amazing views from the living room and primary bedroom of this 2 bedroom/2.5 bathroom. Take a drink outside and sit on your private balcony and watch the incredible sunsets. This beautiful condo sits right on the beach in Holmes Beach. After a day on the beach, take a dip in the community pool or sit ...

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Property Type

Anna Maria Island Condo

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

$459

avg/night

$459
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for the perfect beach destination? Well, it doesn't get better than this! This 2 bedroom/2 bath condo, recently updated, is centrally located on Holmes Beach and is only steps from the sparkling gulf waters and white sandy beaches. New floors, new furnishings and decor - this place is your ...

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Property Type

Anna Maria Island Condo

Featured review

"Tropical Sunset #1"

Location is where it's at! Close to everything, yet on a quiet street. We had a great time celebrating 5 years post cancer! Loved the Island and everyone on it. We didn't want to leave! Loved the way ...

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

$305

avg/night

$305
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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 Condo
1 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 1 bedroom, 1 bathroom
4.8 rating on other travel sites

$325

avg/night

$325
avg per night
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Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Brimming with historic character, this charming ground level 1 bedroom/1 bath cottage has a bright modern, organic feel–and is merely steps from the white sandy beaches. With dramatic vaulted ceilings and secluded garden settings, The Cozzi Cottage offers everything you'd want in a beach vacation. ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island Condo
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom
4.7 rating on other travel sites

$304

avg/night

$304
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Relax, unwind, and make the best beach memories in this beachy home! This home has a fully-equipped kitchen that will make preparing meals easy. Spend time grilling on the private patio after a day of fun on the beach.You are just a seashell's throw from the white sands of the Gulf of Mexico, it ...

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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

$478

avg/night

$478
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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

$436

avg/night

$436
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This amazing beachfront 2 bedroom/2 bathroom condo is perfect for an island vacation. This unit is recently under new ownership and has been completely updated with new paint throughout, all new kitchen appliances and brand-new living room and dining room furniture. The unit features a fully-equipped ...

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Property Type

Anna Maria Island Condo

Featured review

"Breach front paradise"

This is our 3rd vacation on AMI and we love it! This condo is a perfect location with beautiful beach and water views. So close you can watch dolphins from the balcony! The rooms are good, master bed very ...

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

$476

avg/night

$476
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Located right across the street from the world-famous Anna Maria Island beaches, this two-bedroom condo is newly remodeled and updated and is less than 100 steps away from the warm turquoise gulf waters and sparkling white sand. Tropical Sunset #2 is one of only four units in the entire building and also ...

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Property Type

Anna Maria Island Condo

Featured review

"Amazing Location"

Perfect location, beach was less busy because we were far enough away from the public beach area. Plenty of space to set up and not be on top of other people. The condo itself is good and had everything ...

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Anna Maria Island House
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

$345

avg/night

$345
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming home just steps to the beaches. The home creates fun Florida island vibes with two bedrooms perfect for a family or a small group getaway. Anna Maria Hideaway lies within a stone's throw of the trolley stops for guests to hop on ...

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Property Type

Anna Maria Island House

Featured review

"great location"

We enjoyed on our stay at this well-kept property on Anna Maria Island. It offered privacy with a good central location.

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2.5 bathrooms
1 review

$473

avg/night

$473
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Casa Bonita is bright, inviting, and the perfect place for a wonderful vacation with family and friends in a tropical paradise. This home is located in the heart of Bradenton Beach, only a few short steps away from beachfront access and Bridge Street. You can lounge in the sun and enjoy a swim in your ...

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Property Type

Anna Maria Island House

Featured review

"Perfect"

The house was absolutely perfect! It was so nice and the cleanest house we have ever rented. We had everything we needed. We would definitely recommend.

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

$656

avg/night

$656
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Ask about our Winter Special! (January 4th til February 1st, 2025) Great deal!VRC# #This listing, A Lazy River Day and Night includes Both sides of home.Cleaning fee includes Professional Linen Service for all towels and bedding!A leisurely stroll (less than three short blocks) from the ...

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Property Type

Anna Maria Island House

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

$450

avg/night

$450
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

This is it - Paradise! This fabulous Key West style elevated 3 bedroom/2 bath single family home has so many wonderful features it is hard to list them all here. It offers cathedral ceilings, open floor plan, private heated pool & spa, private decks from every room, screened covered deck, ground level ...

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Property Type

Anna Maria Island House

Featured review

"Great all around."

This house was everything and more. Way bigger than pictures. Had everything you could need. Would definitely stay there again.

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

$721

avg/night

$721
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 2 bathrooms

$671

avg/night

$671
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

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
4 BR | 2.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 2.5 bathrooms
4.9 rating on other travel sites

$874

avg/night

$874
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS WITH A CHECK-IN DATE AFTER SEPTEMBER 5, 2023! All Drivers must be over the age of 21. Driver's must provide valid US Driver's License and US Vehicle InsuranceLocated just steps away from the sugary, soft sand and clear ocean water, Salty ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
2 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
4.9 rating on other travel sites

$424

avg/night

$424
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

In the heart of Holmes Beach on Anna Maria Island rests this charming pet-friendly home just steps to the beaches. Misty Beach is a charming coastal home with a flamingo-shaded exterior, quickly moving you onto island time. The interior showcases island artwork, creating a welcoming and calming environment. ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

$1275

avg/night

$1,275
avg per night
View Details

Key Amenities

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

About this property

128 49th St Holmes Beach VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations made on or less ...

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Property Type

Anna Maria Island House

Featured review

"Great Thanksgiving Vacation!"

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

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

$317

avg/night

$317
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

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

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Property Type

Anna Maria Island House

Featured review

"GREAT LOCATION"

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

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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

$552

avg/night

$552
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Summer Breeze is a custom home nestled in the quiet residential area in the heart of Holmes Beach. Offering 4 bedrooms/3.5 bathrooms. There is also a den where the kids can hang out with a TV and sleeper sofa. You will find that this home has everything you need for your perfect Anna Maria Island vacation! ...

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Property Type

Anna Maria Island House

Featured review

"Nice house"

This house was nice, clean and well stocked. The furniture was a bit worn but very comfortable. The yard is small but nicely landscaped and the pool was large enough for our family. The walk to the beach ...

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

$898

avg/night

$898
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

6 PERSON GOLF CART INCLUDED ON ALL NEW RESERVATIONS MADE AFTER 1/24/24 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 InsuranceCoastal Serenity has a rooftop deck, private pool and spa, and an EV Charger! ...

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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

$790

avg/night

$790
avg per night
View Details

Key Amenities

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

About this property

Breathtaking sunset views atop your own expansive and elevated deck await at this spacious single story home on gorgeous Anna Maria Island! This home features 4 large bedrooms, each with its own private en suite bathroom, a large kitchen, living room, additional sitting area plus two separate dining spaces. ...

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Property Type

Anna Maria Island House

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

$500

avg/night

$500
avg per night
View Details

Key Amenities

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

About this property

This upper and lower unit duplex home is located steps from the Gulf of Mexico on historic Anna Maria Island. These Holmes Beach bungalows have a large heated pool and are rented in unison, perfect for friends and large families, as well. Both units are pet friendly. Only 1/2 mile from shops and restaurants ...

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Property Type

Anna Maria Island House

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Anna Maria Island House
5 BR | 4.5 BA | Sleeps 12 | Quick View
Sleeps 12, 5 bedrooms, 4.5 bathrooms

$1054

avg/night

$1,054
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Get ready to pack your bags because you'll be escaping to a tranquil oasis nestled within a lush tropical backyard, where a shimmering pool and soothing spa await your relaxation. Discover the serene charm of A Bean Point Paradise, a retreat boasting 5 bedrooms and 4.5 bathrooms with parking for ...

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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

$602

avg/night

$602
avg per night
View Details

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

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 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms
2 reviews

$331

avg/night

$331
avg per night
View Details

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • WiFi

About this property

Perfectly located 2 bedroom/2 bathroom condo is directly across the street from the gulf beaches. Pelican Cove is located in a small, private complex on a very unique part of the Island. It is one of the few condos with views of both the Gulf and the Bay. Pelican Cove is just 40 yards from one of the ...

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Property Type

Anna Maria Island Condo

Featured review

"Great Stay"

We were actually supposed to stay in # 3,but ended up in #2. The condo was really really clean and we'll stocked. The appliances are up to date,and everything works. Plenty of glasses,pots,pans,utensils ...

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Anna Maria Island House
5 BR | 6.5 BA | Sleeps 8 | Quick View
Sleeps 8, 5 bedrooms, 6.5 bathrooms
4.8 rating on other travel sites

$1125

avg/night

$1,125
avg per night
View Details

Key Amenities

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

About this property

Anna Maria Beach House offers a 5 bedroom and 6.5 bathroom, pet-friendly property, making it a perfect vacation retreat for your whole family. Situated close to the beach, shops, and restaurants, this property is an ideal choice. Just a brief stroll away from the beach, the house boasts a pool and hot ...

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Property Type

Anna Maria Island House

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Anna Maria Island Condo
2 BR | 2 BA | Sleeps 5 | Quick View
Sleeps 5, 2 bedrooms, 2 bathrooms

$516

avg/night

$516
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Sun Plaza West is a beautiful beachfront property offering all of the conveniences you would want in an island stay. This recently updated and remodeled 2 bedroom/2 bathroom condo offers beachfront views and is located in the heart of Holmes Beach featuring an elevator, heated pool, on-site tennis court ...

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Property Type

Anna Maria Island Condo

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

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

This 3 bedroom condo sits close to the Gulf Beaches at Gulf Place Condominium. Sit on the lanai and drink your coffee looking out onto the Gulf.

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Property Type

Anna Maria Island Apartment

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

Key Amenities

  • Air conditioning
  • Pet friendly
  • 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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Property Type

Anna Maria Island House

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

Key Amenities

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

About this property

To Book Directly please visit: /its-miller-time 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: This custom 4 bed 4.5 bath home was built with no expense spared! Custom kitchen ...

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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 6 | Quick View
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review
owner special
Owner special: Contact us and receive 10% off your next vacation! Mention COASTAL10!

$313

avg/night

$313
avg per night
Owner special:
Contact us and receive 10% off your next vacation! Mention COASTAL10!

View Details

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

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) * Open Air Balcony off Master Bedroom * Screened Lanai with Patio Furniture * 3rd Balcony with view ...

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Property Type

Anna Maria Island Condo

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Anna Maria Island House
3 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 3 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to The Blue Ark: “A Place of Refuge”.***7-night minimum, Saturday to Saturday Only.Amenities you’ll love:* Bay views from 3 stories * 0.2 mile walk to the beach and 0.1 mile walk to one of the island’s trolley stops * Elevator for easy access to all 3 floors * ...

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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
3 reviews

$630

avg/night

$630
avg per night
View Details

Key Amenities

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

About this property

Welcome to paradise- AMI VILLA! When you come to Anna Maria Island for vacation, make this charming Mediterranean beach 3 bedroom & 3 bath villa your home away from home! With much to offer, this home will have your family wanting to return to Anna Maria Island year after year.Features include: -3 ...

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Property Type

Anna Maria Island Villa

Featured review

"Perfect for my family!"

This house is perfect for a large family. 3 bedrooms and 3 full baths. Close to the beach and provides everything you need! Chairs, umbrellas and a wagon to use to transport everything. Even an ice ...

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

$291

avg/night

$291
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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Anna Maria Island Townhome
3 BR | 2 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2 bathrooms
4.5 rating on other travel sites

$639

avg/night

$639
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

VRC 304 60th St Unit A Holmes Beach FL 34217Cancellations up to 30 days prior to arrival result in a refund of 70% of the grand total. In the event the reservations exceeds $20,000 or 30+ days, cancellations must be made prior to 45 days prior to arrival in order to receive 70% of the grand total.Azure ...

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Property Type

Anna Maria Island Townhome

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Anna Maria Island House
3 BR | 2.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 2.5 bathrooms
4.8 rating on other travel sites

$582

avg/night

$582
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

312 A 61st Street Holmes Beach, FL 34217 VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations ...

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Property Type

Anna Maria Island House

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Anna Maria Island Townhome
3 BR | 3.5 BA | Sleeps 6 | Quick View
Sleeps 6, 3 bedrooms, 3.5 bathrooms
1 review

$650

avg/night

$650
avg per night
View Details

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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Property Type

Anna Maria Island Townhome

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

$303

avg/night

$303
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

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 ...

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Property Type

Anna Maria Island Condo

Featured review

"Stunning Accommodation"

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

Distance to beach: 0.5 miles to Manatee Beach

$243

avg/night

$243
avg per night
View Details

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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Property Type

Anna Maria Island Condo

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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Anna Maria Island House
4 BR | 4.5 BA | Sleeps 8 | Quick View
Sleeps 8, 4 bedrooms, 4.5 bathrooms

$940

avg/night

$940
avg per night
View Details

Key Amenities

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

About this property

What You'll Love About This Home:Location! 3 Blocks to the Beach! 4 Bedrooms / 4 Bathrooms 3 King Beds, Two Sets of Bunk Beds with Twin Bed over Full Bed Lagoon Style Heated Pool w/ sundeck & Spa In Pool Umbrellas Pool Deck Lounge Chairs Poolside Covered Lounge with Patio Furniture, ...

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Property Type

Anna Maria Island House

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

$212

avg/night

$212
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Enjoy beautiful Anna Maria Island relaxing in a spacious ground floor condo unit with 2 bedrooms and 2 baths overlooking the heated community pool. This quiet slice of paradise has a large screened lanai off the living room with a pool view. Enjoy the amazing white sand beach and gorgeous sunsets within ...

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Property Type

Anna Maria Island Apartment

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

$557

avg/night

$557
avg per night
View Details

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

306 67th Street Unit B Holmes Beach, FL 34217 VRC You may cancel your reservation up to 60 days before check-in for a full refund minus a $495 processing fee and less 3rd party travel insurance fees, if applicable. The refund will be made to the original payment method. After that time, or for reservations ...

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Property Type

Anna Maria Island House

Featured review

"Cozy & Comfy"

This home was exactly what we were looking for. It was a minute walk to the beach, 1 1/2 blocks. The home was equipped with everything we needed, including beach, chairs, umbrellas, and a cart to lug everything ...

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Anna Maria Island Cottage
2 BR | 1 BA | Sleeps 4 | Quick View
Sleeps 4, 2 bedrooms, 1 bathroom
10 reviews

$286

avg/night

$286
avg per night
View Details

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

A guest had this to say: "Songbird is a cute little purple house on a quiet side street on Anna Maria Island. I referred to the house as little, it is really quite spacious & comfortable. This is our 6th stay at Songbird & we are looking forward to our next stay. This trip we were on side ...

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Property Type

Anna Maria Island Cottage

Featured review

"Splendor in the sun"

Second time staying here and actually lucked out with a cancellation. 2 week stay and couldn’t have been better timing weather wise. Short couple block walk to the pristine white sand beaches. Easy haul ...

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Anna Maria Island Cottage
2 BR | 1 BA | Sleeps 6 | Quick View
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • WiFi

About this property

Nestled just 1.5 blocks away from the pristine shoreline, this charming duplex offers the quintessential beachside retreat. Boasting two bedrooms and one bath, it's an inviting haven for those seeking both comfort and coastal living. As you step inside, you're greeted by an atmosphere of relaxed ...

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Property Type

Anna Maria Island Cottage

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Holmes Beach (Anna Maria Island, Florida) Vacation Rentals

Enjoy Your Dream Vacation at Holmes Beach on Anna Maria Island

Located off the Florida coast just south of St. Petersburg, Anna Maria Island is a popular vacation destination known for its stunning beaches, tasty restaurants, and extensive activities.

Homes Beach is widely considered to be Anna Maria Island’s crown jewel, making it the perfect place to plan your Anna Maria Island vacation.

Endless Possibilities and Activities

At Holmes Beach, Florida, you’re not likely to run out of activities, no matter what your interests might be. Watersports like sailing, jet skiing, parasailing, and more are a common pastime along the shores of Holmes Beach.

The waters are calm enough to swim in while still providing plenty of great waves for your favorite sports. And if you prefer to simply relax by the waves rather than being in them, you’ll feel at ease laying back on the white sandy beach.

Incredible Weather Year-Round

Like most of the Florida coast, there’s no bad time to visit Holmes Beach weather-wise. The warmest days with the lowest humidity usually occur in the fall, but you’re sure to enjoy plenty of sunshine and light breezes during your trip, regardless of the season. No matter what time of the year you visit, you won’t have to miss out on any of the quintessential Florida experiences.

The Best Way to Experience Anna Maria Island

If you want to make the most of your journey to Anna Maria Island, you shouldn’t stay anywhere other than Holmes Beach rentals. Many of the island’s most sought-after restaurants, bars, and shops are located at Holmes Beach. With all that and one of the Florida coast’s most inviting beaches, you can’t go wrong with Holmes Beach as your destination.

Book early to make sure you secure your dream vacation home at Holmes Beach, Anna Maria Island. Find it now among our wide selection at FloridaRentals!