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Anna Maria Island Vacation Rentals

(232 rentals)
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

Underwent complete INTERIOR REMODEL in Jan 2023!!! This Bean Point beauty is perfect for the family or group wanting to be ultra close & steps to one of the most beautiful sought after beaches in Florida! Aside from the fantastic location, this elevated 3 Bedroom 2 bath home has two amazing decks ...

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$898
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

Click on calendar for available 2025 dates. Book now before they are gone! CALL FOR UNBELIEVABLE SAVINGS. ONLY PHONE CALLS GET DISCOUNTS. July 26- August 16th, 2025 is available now. Special rate is available.TWO WEEK MINIMUM STAY. No exceptions. No Pets. Sorry.20 STEPS TO THE SAND - GREAT ...

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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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$245
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

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

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$175
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 2 bathrooms
2 reviews

Key Amenities

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

About this property

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

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Featured review

"Big Joe"

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

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$127
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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$305
avg per night

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Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms
1 review

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

Be one of the very first to stay in this LUXE, newly constructed custom home. Heated pool & spa, rooftop deck with GULF VIEWS. Grill, custome kitchen, wet bar on thrid level. ALL THE BELLS AND WHISTLES! This stunning 4 bedroom + bonus room (2 additional twin beds), 5 bathroom home only 2-minute ...

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Featured review

"Holmes beach"

This is an amazing property! Location and pool and lanai were awesome! Private and close to everything! There was a Publix right up the road also. We rented golf carts from zoom around and we could easily ...

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$680
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 3 bathrooms

Key Amenities

  • Air conditioning
  • Hot tub
  • Pet friendly
  • WiFi

About this property

Welcome to Waves - Your Perfect Anna Maria Island Getaway!Experience the ultimate beach retreat at Waves, a luxurious 4-bedroom, 3-bathroom vacation home located on the picturesque Anna Maria Island. Nestled just across the street from the sun-kissed sands and azure waters of the beach, this property ...

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$1,038
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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$155
avg per night
Anna Maria Island Condo
Sleeps 4, 2 bedrooms, 2 bathrooms
5 reviews

Distance to beach: 0.5 miles to Manatee Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

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

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Featured review

"Fabulous stay on Anna Maria Island"

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

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$134
avg per night
Anna Maria Island House
Sleeps 8, 3 bedrooms, 2 bathrooms

Key Amenities

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

About this property

** Damage from the storm restored! Open for Bookings! **Your Private Oasis Awaits at Isla Living! Discover a haven of comfort and style in our meticulously curated Airbnb accommodations. Immerse yourself in modern amenities and local charm, where each space tells a unique story. Whether you seek a ...

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$738
avg per night
Anna Maria Island Cottage
Sleeps 4, 2 bedrooms, 1 bathroom
12 reviews

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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Featured review

"Home away from home."

My wife and I have enjoyed the Songbird Cottage on Anna Maria Island several times in the last few years. It’s located in a nice, quiet neighborhood only a few minutes from the beach by bike. The two ...

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$120
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms
4 reviews

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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Featured review

"Great Property"

The property had everything we needed. It was very cozy! We loved the location and how it was within walking distance to everything we wanted to do. The pool was amazing! We hope to return!

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$147
avg per night
Anna Maria Island House
Sleeps 4, 2 bedrooms, 2.5 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront

About this property

The Beach House is a charming beach bungalow nestled among numerous Australian pines and sea grapes. A unique setting directly on the Gulf of Mexico shaded among the trees. Walk out the back door on your private path to a white sugar-sand beach. Best of both worlds, you have the shade and sunny beach. The ...

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$545
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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$235
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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$472
avg per night
New
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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$196
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 Townhome
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

VRC 304 60th St Unit A Holmes Beach FL 34217Escape to Azure Beach House—a stunning 3-bedroom, 2-bathroom vacation home nestled in the heart of Holmes Beach on Anna Maria Island. Located just minutes from the pristine Gulf beaches, this beautifully designed home offers the ideal setting for ...

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$385
avg per night
New
Anna Maria Island House
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

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

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$183
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Sweet Home Anna Maria! Walk to Manatee Public Beach, Grocery Stores, Restaurants, Shopping & More! Private Heated Pool & Hot Tub with Plenty of Seating for the Whole Family! Game Room with Ping Pong, Dart Board, Extra Fridge & Bathroom Every Bedroom has an Ensuite Bathroom! ...

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$377
avg per night
Anna Maria Island Apartment
Sleeps 4, 2 bedrooms, 1 bathroom
4 reviews

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

Key Amenities

  • Air conditioning
  • Beachfront
  • WiFi

About this property

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

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Featured review

"Beautiful Property"

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

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

Key Amenities

  • Air conditioning
  • Hot tub
  • Private pool
  • WiFi

About this property

It’s all about location on vacation, and Reef Romance does not disappoint! Sail away to this beautiful four-bedroom, four-and-a-half-bathroom custom-built home for a dose of luxury at the beach. Located on the prestigious north end of Anna Maria Island, you’re just a few houses away from the ...

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$766
avg per night
Anna Maria Island House
Sleeps 6, 3 bedrooms, 3 bathrooms
5 reviews

Distance to beach: 250 feet to About a 50 second walk

Key Amenities

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

About this property

This home was great before but now it's undergone a 2+ year no expense spared renovation making it exceptional in every way! Our newest 3 bedroom/3 full bathroom home is one of the most deluxe vacation rentals available on Anna Maria Island and located in most sought after part of island and only ...

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Featured review

"Excellent"

This house is in a great location close to the beach, the pier and bridge street. The kitchen is probably one of then best stocked I have ever scene. I highly recommend this house. Great indoor and outdoor ...

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$423
avg per night
Anna Maria Island Apartment
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Brand New Listing! Hello Sunshine...Take time and breathe again at this special and tranquil getaway. This 1 bedroom 1 bath corner unit is in a charming beachside complex with a lovely pool & gardens directly across & just 20 steps from the beautiful beaches of Anna Maria Island & the sparkling ...

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$233
avg per night
New
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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$209
avg per night
Anna Maria Island Villa
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Sea Site Unit B! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Private Patio for Beach Equipment and Grilling King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWelcome, too Sea Site Retreat Unit B! ...

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

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to Sea Site Unit A! 100 Steps to the World Class Beaches of Anna Maria Island Close to Restaurants, Shopping, and More Water Views from Balcony King, King, & Two Full Beds High speed Wi-Fi & Smart lock for Self-Check-inWaking up to a view of the coast with your morning cup of ...

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$299
avg per night
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • WiFi

About this property

Welcome to "Down On The Island" the perfect beach destination for your next family getaway! .01 Miles to the World Class Beaches of Anna Maria Island Nearby Park with Basketball, Playground, Kayak Launch Fully Stocked Kitchen for Home-Cooked Delights Seamless Arrival with Fast Wi-Fi & ...

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$271
avg per night
New
Anna Maria Island Condo
Sleeps 6, 2 bedrooms, 1 bathroom

Key Amenities

  • Pool
  • WiFi

About this property

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

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$185
avg per night
Anna Maria Island House
Sleeps 17, 7 bedrooms, 7.5 bathrooms

Key Amenities

  • Air conditioning
  • Pet friendly
  • Private pool
  • WiFi

About this property

Welcome to Ocean Star! .01 Miles to Amazing Gulf Coast Beaches Private Heated Pool/Spa with Outdoor Seating & BBQ Beach Equipment Available for Use Every Bedroom Has a Private Bathroom Fully stocked kitchen for all of your favorite home-cooked meals High-speed Wi-Fi, Smart lock for Self Check-in ...

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$855
avg per night
New
Anna Maria Island Condo
Sleeps 4, 1 bedroom, 1 bathroom

Key Amenities

  • Air conditioning
  • Pool
  • WiFi

About this property

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

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$169
avg per night
New
Anna Maria Island House
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Beachfront
  • Private pool
  • WiFi

About this property

Reel Coastal PropertiesThe space Highlights • 2-minute walk to the Beach of Anna Maria Island • 5-minute walk to Pine Ave. • Private Pool • Outdoor Shower • Beach gear (chairs, umbrella, towel, kids toys)Blue Mermaid by Reel Coastal Properties 111 Sycamore Ave Anna ...

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$397
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 232 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 $105 per night with an average price per night of $299.

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 162 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 13 oceanfront rentals in Anna Maria Island available on FloridaRentals.com. Use our filters to search and book yours today!