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Anna Maria Island Vacation Rentals

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

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect beach getaway! This beautifully renovated 2-bedroom, 2-bathroom condo comfortably sleeps up to 4 guests and offers everything you need for a relaxing coastal escape.The primary bedroom features a luxurious king-size bed and a private ensuite bathroom with a spacious walk-in...

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$128
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Bimini Sunrise special: - Concierge Collection Property - Golf cart included! - Anna Maria on Anna Maria Island - A short walk to Pine Avenue - Spacious heated pool / spa - Rooftop deck, elevator, private dock - Gas grill (propane included) - Professional Linen Service -...

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$657
avg per night
Anna Maria Island House
Sleeps 16, 7 bedrooms, 6 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • 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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$677
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 VRC19-000273 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool + Spa | Pet-Friendly This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors Completely Renovated February 2025! Welcome to Conch-Out Beach...

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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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$482
avg per night
Anna Maria Island Villa
Sleeps 12, 4 bedrooms, 4 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Ideal Location - Family Vacation Accommodation 2 Individual Villas, 4 Bedroom 4 Baths Sleeping for 8-12 Guests Pricing is for one villaDuring January February & March you can only rent 1 villa. During June & July you must rent both villas. Pricing on our site here is for only 1 villa.The...

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Featured review

"Huge pool and awesome location"

We had a great time and our kids loved the pool! We rented bikes and used them everyday. We had a party of 12 and it was big enough for all. We would love to stay again!

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$214
avg per night

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Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Hot tub
  • Pool
  • WiFi

About this property

Relax in the modern 3BR 2.5Bath condo in the majestic beachfront neighborhood in Bradenton Beach, FL. Soak up the sun by the two community swimming pools, or walk down to the sandy beach and experience the beautiful Gulf Coast.The picturesque location will leave you speechless!The Space HURRICANE...

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$221
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 4.5 bathrooms
12 reviews

Key Amenities

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

About this property

This luxurious property offers a perfect blend of indoor and outdoor living, with spacious accommodations for large groups or families, all while staying steps from the pristine white sand beaches and centrally located on Anna Maria Island!As you step through the front door, you enter a bright and...

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Featured review

"Best Stay Ever!"

I’d give it a 10 star! Absolutely perfect vacation rental! About a block and a half from beach no busy road to cross to get there! We could see the ocean from the front porch. The home is clean, fully...

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$514
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Just a block and a half from the beach, this bright and airy elevated pool home offers the perfect blend of relaxation, comfort, and coastal convenience. With 3 bedrooms and 3 full bathrooms, this spacious single-family retreat is thoughtfully designed for both families and groups looking to enjoy beachside...

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$307
avg per night
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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$202
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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$182
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

Looking for a prime location to vacation? Seagrass Flats Unit 1 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops, vinyl plank flooring...

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Featured review

"Outstanding!"

We enjoyed our stay at Seagrass Flats. Our unit was very clean, well furnished, and worked great for our vacation with the in-laws. Beds were comfy and we appreciated the little extras, like beach towels...

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$183
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Looking for a prime location to vacation? Seagrass Flats Unit 2 is a 2 bedroom/2 bathroom condo that is located less than 75 steps to the Gulf and has a shared heated pool. This unit has been completely renovated both inside and out. Bathrooms and kitchen feature quartz countertops; vinyl plank flooring...

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Featured review

"Would stay again"

I want to start by saying the accommodations were nice and the location is excellent. We would stay here again. The rest of my comments or for the rental company, owner and future renters. The check in...

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$183
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Island Dream is your perfect coastal escape. This spacious 4-bedroom, 4-bathroom coastal retreat with a fully equipped kitchen and a stunning backyard perfect for outdoor entertaining. Ideally located near the beach, shops and restaurants, it offers the perfect blend of comfort, convenience and relaxation.Step...

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Featured review

"Awesome home!!"

The house and all the amenities were perfect!! The kitchen, dining area, bar seating at island and being open to family room was really nice!! The bedrooms were spacious, having own bathrooms was great...

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$361
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

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 an elevator, cathedral ceilings, open floor plan, private heated pool & spa, private decks from every room, screened covered deck,...

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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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$246
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 2 bathrooms
4 reviews

Key Amenities

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

About this property

One of the highest rated vacation homes on Anna Maria Island with more than 160 five-star ratings from Airbnb/VRBO!Stay at the home of a NY Times best-selling food writer! Big 5-bedroom house, pet friendly, lots of space and charm, great location (5-min walk to beach) with private lagoon-style heated...

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Featured review

"Family vacation"

We truly enjoyed our stay at Kathleen’s house. We had a 11 month and a 3 yr old and it was so nice to have so much baby and kid stuff supplied. We rented a Golf cart which was great to have for transporting...

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$685
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to your island retreat in the heart of Holmes Beach, Florida. This pet-friendly property offers a light-filled, thoughtfully laid-out interior that blends coastal charm with everyday comfort, perfect for your vacation getaway.The main living space features an open-concept design with warm...

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$261
avg per night
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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$252
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 VRC17-000113 Fully Renovated February 2025 Welcome to Beach Bliss, a beautifully updated 3-bedroom, 3-bathroom...

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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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$336
avg per night
Anna Maria Island House
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Island Charm special: - Holmes Beach on Anna Maria Island - Short 5 min walk to Gulf Beaches - Heated pool - sun shelf and dining in pool - Grill (propane included) - Professional Linen Services - Complimentary WiFI - Beach chairs, beach wagon & beach umbrella - Parking...

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$293
avg per night
Special Offer
Anna Maria Island Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
3 reviews

Key Amenities

  • Air conditioning
  • Beachfront
  • Pool
  • WiFi

About this property

Escape to paradise in this beautiful 3-bedroom, 2-bathroom vacation rental home located just steps away from the white sandy beaches.The spacious living area is perfect for relaxing after a day at the beach, with comfortable seating and a large flat-screen TV. The kitchen is fully equipped with everything...

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Featured review

"Fabulous on beach condo"

This 3 bedroom, 2 bath condo in Holmes Beach was a fabulous place for our vacation of 6 retirees. From the spacious living area, open kitchen, sunny lanai, pool and good size bedrooms to being located...

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$288
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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$296
avg per night
Last Minute Deal
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

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

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Featured review

"Excellent Stay"

Location was perfect! Condo had everything we needed, nicely decorated and clean. Morgan was wonderful to work with. Thanks Morgan!

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$128
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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$558
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Costa Lotta is "home away from home”. All the amenities you will need in this 2,100 sq.ft. home. Costa Lotta is the perfect vacation spot for relaxation on Anna Maria Island! Just 200 steps and you are on a gorgeous, white sandy beach looking at the spectacular Gulf of Mexico! Walking distance...

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$325
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Pelican Cove is a beautiful Gulf to Bay property with a prime location just steps to the beach, five-star restaurants, shops and more - it's the tropical vacation you've been dreaming of offering you all of the conveniences you would want in an island stay. This beautiful condo was completely...

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Featured review

"Great Island Location"

Clean, cute updated condo. Photos represent the property correctly. Great view of the bay, right on the water. Only a short walk across the street to the beach. Easy walk (5 blocks) to great shopping...

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$187
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2.5 bathrooms

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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$177
avg per night
Anna Maria Island House
Sleeps 10, 5 bedrooms, 3 bathrooms
2 reviews

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Recently renovated! Flip Flops Forever is a traditional Florida home just steps from the beach nestled in the quiet residential area in the heart of Holmes Beach. Offering 5 bedrooms/3 bathrooms, Flip Flops Forever is located in the perfect location for a great family vacation. Only a few seconds walk...

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Featured review

"Perfect Beach House for just about anyone"

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

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$372
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your perfect coastal getaway on beautiful Holmes Beach, just one block from the shimmering Gulf of Mexico with its turquoise-blue waters and powdery white sand. This charming 3-bedroom, 2.5-bath single-family home captures the essence of Anna Maria Island living, featuring soft pastel interiors...

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$287
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Looking for a great vacation location on beautiful Holmes Beach? Then look no further. Island Haven is a two-story, private home that features 4 bedrooms (two of which are primary bedrooms), 3 full bathrooms, game room and private saltwater, heated pool. Upon entry, you will find the open-concept living...

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$344
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

A 2-bedroom, 2-bath coastal condo perfectly positioned across the street from the white sands of Bradenton Beach on Anna Maria Island. Seagrass Sunsets delivers comfort, charm and an unbeatable Bradenton Beach location. Seagrass Sunsets is your effortless home base for Gulf Coast Living.You'll...

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$166
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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$351
avg per night
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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$206
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Bay Breeze Bungalow special: - North end of Anna Maria - private home on cul-de-sac - Pool (not heated) - Canal front with 15 ft dock (6 ft clearance) - Enclosed screened-in patio - Grill (propane included) - Professional Linen Services - Complimentary WiFi - Beach chairs,...

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$310
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Recently Renovated!Welcome to your perfect beach retreat! This beautifully renovated 2 bedroom/2 bathroom condo offers fresh charm with brand new stainless steel appliances, new flooring, and stylish new furniture and decor throughout. Every detail has been thoughtfully updated, and you get to be...

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$170
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Private 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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$220
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • 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....

View all property information

$611
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
24 reviews

Key Amenities

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

About this property

Located on 5th Avenue in Holmes Beach this unit is out of the way on a dead end street. Seaduction offers a heated pool, and every amenity to make your stay here a comfortable one. There are only 4 units in the complex so to pool is "semi private".This beautiful unit sleeps six with a king...

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Featured review

"Wunderschöne Wohnung"

Wir haben eine Woche in der Wohnung auf Anna Maria Island verbracht. Es war traumhaft schön. Die Wohnung ist sehr gut ausgestattet: vom Eiswürfelspender bis zur Waschmaschine, vom Strandwegen mit Stühlen...

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$219
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2.5 bathrooms

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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$307
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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$204
avg per night
New
Anna Maria Island House
Sleeps 14, 7 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

A few things that make Blue Azure special: Concierge Collection Property Golf cart included on any reservation made after 6/18/26! Bradenton Beach on Anna Maria Island - 4 min walk to Gulf Beaches Pool / spa, rooftop deck Putt putt golf, ping pong, corn hole, Connect 4 Lower level refrigerator Gas...

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$633
avg per night
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom
1 review

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

35 Steps to the Sea at Runaway Bay 112 is a 1 bedroom/1 bath, ground floor condo that can sleep 4. Featuring the largest heated pool on the island, private beach access, gym, and an array of amazing amenities, this ground-floor condo is your perfect home base on the Gulf Coast. The fully-equipped kitchen...

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Featured review

"Fantastic vacation all around"

This was a very nice condo. Clean and well kept. Very close to the beach and to the pool. Location was everything we wanted. Walking distance to restaurants and the heart of town. Great food, great people....

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$124
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2.5 bathrooms
13 reviews

Key Amenities

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

About this property

This affordable & convenient 3 story home is one house off Holmes Beach. It has fantastic 2nd & 3rd level balcony beach views with no obstruction over the one story house in front of mine with no trees. The 3 bedroom 2.5 bath villa with 2 car garage accommodates 6 guests and is 150 feet from the...

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Featured review

"Great Location and Spacious Condo"

We spent a wonderful month in this unit. You can see the beach from the front balcony as it's just across the street. It's very spacious with an open concept living room, kitchen and dining area. It...

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$386
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

Paradise Found - with Pool & Hot Tub 401 42nd Street, Holmes Beach, FL 34217 VRC17-000010 5 Bedrooms | 6.5 Bathrooms | Sleeps 12 | Heated Pool & Hot Tub ​​​​​​​ Pet Friendly This home can park up to 4 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation...

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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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$570
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Welcome to your ultimate beachside escape! This beautifully renovated 2 bedroom, 2 bathroom condo offers the perfect blend of modern style, comfort and location. Whether you're here for a quick escape and a longer stay, "Days Like This" at Runaway Bay 116 offers everything you need for...

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$151
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 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....

View all property information

$874
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

Mermaid's Crossing by Beach Retreats Vacation Rentals 210 65th St, Holmes Beach, FL 34217 VRC17-000007 4 Bedrooms | 3 Bathrooms | Sleeps 8 | Heated Pool & Hot Tub This home can park up to 3 vehicles Quiet hours at 10p-7a: please respect neighbors No cancellation fees! Cancel 60+...

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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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$454
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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$278
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Resting Beach Place 5608 Gulf Dr, unit 111, Holmes Beach, FL 34217 VRC21-000018 2 Bedrooms | 2 Bathrooms | Sleeps 4 | Community Pool This home has one assigned parking spot. Quiet hours at 10p-7a: please respect neighbors Book with confidence: NO CANCELATION FEES Cancellation Policy $500...

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$265
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

This beautiful second-level condo offers the perfect blend of comfort and coastal charm. With 2 bedrooms and 2 bathrooms, Starfish Haven is ideal for families, friends, or a relaxing getaway. Step into a bright and inviting open-concept living space, where the kitchen features stainless steel appliances,...

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Featured review

"Excellent beach vacation"

Such a pleasant stay, great location for walking to restaurants, shops, steps from the beach. We loved staying on the island it's been years since we've been and really appreciated all that it has to offer....

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$161
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom
3 reviews

Key Amenities

  • Air conditioning
  • Private pool
  • WiFi

About this property

Sunset Azul is a fully-updated 2 bedroom/1 bath gulf-side ground level villa on the southern end of Holmes Beach. It's quiet, yet close to shopping, restaurants and trolley stops. Best of all, this unit is only a few short steps to the white sandy beaches. This villa has a fully-equipped kitchen,...

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Featured review

"Beautiful place - Highly recommended!!"

This is a great condo!! Full kitchen, washer and dryer IN unit, comfortable bed and beautiful natural light throughout. Only a 2 minute walk to the Gulf beach, Walgreens and Public. 2 parking spots are...

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$171
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 291 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 $79 per night with an average price per night of $285.

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 215 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 24 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!