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Holmes Beach (Anna Maria Island, Florida) Vacation Rentals

(134 rentals)
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

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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$372
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

VRC16-000137 Welcome to "Luana Breeze" located at 208 68th Street, Holmes Beach. Find ease and relaxation the moment you arrive, this property is about 100 steps to the Gulf of Mexico and one of the best beaches on the West Coast of Florida.This ground level beach house offers 4 bedrooms,...

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Featured review

"A True Retreat"

This is a true retreat any time of the year. The backyard and pool area is well designed and an oh so private area that includes a hot tub, a pool, ping pong table, mini golf and hammocks for relaxing....

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$792
avg per night
Anna Maria Island Bungalow
Sleeps 4, 1 bedroom, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • WiFi

About this property

VRC16-000680 The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit B.Unit B: Visit Unit BWelcome to “The Magic Dolphin A” an elevated vacation rental located on the...

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Featured review

"Magic Dolphin A"

We had a wonderful stay at Magic Dolphin A. The unit was very clean and well maintained, which made settling in easy and comfortable. The beds were especially cozy- we slept great throughout our trip.It...

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$293
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private 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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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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$274
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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$386
avg per night

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New
Anna Maria Island House
Sleeps 8, 3 bedrooms, 3 bathrooms

Key Amenities

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

About this property

Location, Location, LocationStaying near the Holmes Beach public beach means you get the best of the island without the hassle:Easy, stress-free beach access (no long walks or parking) Nearby public amenities like restrooms, showers & lifeguards Walk to restaurants, cafes & beach...

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$788
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

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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$417
avg per night
Anna Maria Island House
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

A three-minute walk with easy access to the sugar sand beach on the famous Anna Maria Island. This newly remodeled, pet-friendly 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 from the trolley...

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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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$269
avg per night
Anna Maria Island Bungalow
Sleeps 4, 1 bedroom, 2 bathrooms

Key Amenities

  • Air conditioning
  • WiFi

About this property

VRC16-000681 The Magic Dolphin Unit A and B can be booked together for larger groups up to 8 people. Please call our office or use the link provided below to check availability on Unit A.Unit A: Visit Unit AWelcome to “The Magic Dolphin B” an elevated vacation rental located on the...

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$291
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

NEW MANAGEMENT! Spend your days at the beach, your afternoons by the pool, and your evenings unwinding at Cheerful North Beach Getaway — a peaceful island villa just a three-minute walk from the soft white sands of the Gulf in Holmes Beach on Anna Maria Island.This freshly renovated 2-bedroom,...

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$233
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

VRC19-000080 Come experience Unit 204 at Sun Plaza West on beautiful Anna Maria Island. This 2-bedroom 2-bathroom Condo is in the heart of Holmes Beach within walking distance to restaurants, shopping, and the Islands Free Trolley. Sun Plaza West complex offers secure entry, an elevator, heated pool,...

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$314
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

Seahorse Beach House by Beach Retreats Vacation Rentals 202 81st St, Holmes Beach, FL 34217 VRC17-000118 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub Pet Friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsBook with confidence:...

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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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$561
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 VRC19-000188 4118 5th Ave, Holmes Beach, FL 34217 6 Bedrooms | 3.5 Bathrooms | Sleeps 12 | Elevator | Heated Pool & Hot Tub This home can park up to 4 vehiclesWelcome to Angel Sea—a stunning 6-bedroom, 3.5-bathroom vacation home designed...

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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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$856
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Chasing Waves by Beach Retreats Vacation Rentals 107 78th St, Holmes Beach, FL 34217 VRC21-000089 2 Bedrooms | 2 Bathrooms | Sleeps 6 This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighbors “You are vacationing in a residential area. Please be a good neighbor...

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$271
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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$406
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 Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private 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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Featured review

"Sun plaza west unit 215"

One of the best sunsets views on Ami clean well maintained condo, the grounds have been updated the tenants are wonderful we look forward to coming back every year

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$276
avg per night
New
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Wake up just steps from the sugar-white sands and sparkling shoreline in this beautifully updated coastal retreat. Perfectly positioned across the street from the beach, this inviting 2-bedroom, 2-bathroom condo offers the ideal blend of comfort, style, and convenience.Inside, the space feels light,...

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$208
avg per night
Anna Maria Island Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
15 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Quiet Nights of Quiet Stars on Anna Maria IslandThe Vibe: Quiet, Comfortable, and Updated for 2025 Escape to "Songbird," a charming purple getaway tucked away on a peaceful side street. If you’re looking for a clean, ground-level home where the "quiet nights and quiet stars"...

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Featured review

"Just what we needed"

My wife and I have been coming to A.M.I. since about 2016 and have never actually stayed on the Island. We really wanted to come and stay on the Island this year so I came across Songbird Cottage and as...

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$131
avg per night
Anna Maria Island Bungalow
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

The Blue Haven by Beach Retreats Vacation Rentals 322 64th Street Holmes Beach, Anna Maria Island VRC25-000096 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighbors Please note: The pool technician will need to...

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Featured review

"Wonderful stay!"

This was our first time on Anna Maria and we loved it. Beautiful home. Fully equipped, everything seemed new and updated. Small pool but really nice set up with great outdoor furniture, grill. The beds...

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$306
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

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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$238
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Salt Air East by Beach Retreats Vacation Rentals 7106 Marina Ave Holmes Beach, FL 34217 ​​​​​​​VRC19-000278 2 Bedrooms | 2 Bathrooms | Sleeps 6 | Heated Pool Pet friendly This home can park up to 2 vehicles Quiet hours at 10p-7a: please respect neighborsBook with confidence:...

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$274
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
9 reviews

Key Amenities

  • Air conditioning
  • Rentals by owner
  • WiFi

About this property

Repairs are complete! Peacock Place is back! Many of our beloved regulars who cannot wait to return have secured their time - but there is still lots of availability!Peacock Place is now a three-bedroom, two-bath home and can sleep six adults. Large living room with HDTV & Roku and a big kitchen....

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Featured review

"We had a wonderful time in "old Florida", and were lucky enough to do it again"

My husband and I stayed in the Peacock house 2 years in a row and loved it. Denise is an excellent host and the house was amazingly roomy. The kitchen was outfitted with every item you could imagine....

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$429
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

28-Night Minimum Maximum capacity shall not exceed 6 personsWelcome 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...

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$160
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, and...

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$836
avg per night
Anna Maria Island Condo
Sleeps 5, 2 bedrooms, 2 bathrooms
6 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Oceanfront
  • Private pool
  • Rentals by owner
  • WiFi

About this property

TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT VIEWWe are cheaper than any two bedroom, two bath on the island. We are priced to stay booked.Private high speed internet!This gorgeous open concept, two bedroom, two bath, family room, dining area and kitchen...

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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 House
Sleeps 8, 4 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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$527
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms

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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Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Property Highlights: - Short walk to the beach - Accommodates up to 4 guests - 2 king beds - Private screened balcony - Tasteful coastal décor throughout - Fully equipped kitchen - Indoor and outdoor dining space with room for 4 - Beach essentials: chairs, umbrella, cart - Covered parking...

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$155
avg per night
Anna Maria Island Villa
Sleeps 8, 3 bedrooms, 3 bathrooms
1 review

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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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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$515
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

BRAND NEW LISTING! Beautiful Gulf-front, 2 br 2ba, second-story condo directly on the beach. Our unit 216 is a 5-star listing at Tiffany Place Condominiums, with stunning sunset views from the top-floor private balcony. The master bedroom faces the brilliant Gulf of Mexico waters and includes a California...

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$399
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

30 day stays make this condo community wonderfully quiet and special. The view overlooks the big pool and the Bay. Bring your swimsuit, we are a short distance to AMI's famous white sand beaches, umbrella, beach canopy, cooler, beach towels, and chairs make for a perfect beach day and sunset and...

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$201
avg per night
Anna Maria Island Villa
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Beachcomber showcases spacious decking and a bright, open-concept living, dining, and kitchen area, radiating coastal luxury and charm. The main bedroom features a sumptuous king-size bed and a stylish en-suite bathroom with a soaking tub and a shower, while the second bedroom can be configured as either...

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Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Have you been dreaming about the water here on Floridas Beautiful Gulf Coast? Well, come enjoy "Bay Dreamin" Walk To Bayfront Park located directly across the street! .03 Miles to Pine Ave. Fishing, Shopping, Restaurants, and more! Private Heated Pool/Spa, Putt-Putt Golf Fully Renovated...

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$571
avg per night
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