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Anna Maria Island Vacation Rentals with Private Pool

(165 rentals)
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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$226
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.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 ...

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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
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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$226
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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$473
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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$375
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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$682
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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$498
avg per night
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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$911
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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$256
avg per night
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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$406
avg per night
Anna Maria Island House
Sleeps 8, 4 bedrooms, 4.5 bathrooms

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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$666
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 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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$248
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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$1,050
avg per night
Anna Maria Island House
Sleeps 12, 4 bedrooms, 3 bathrooms
1 review

Key Amenities

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

About this property

Check out our new Summer Last Minute Deals!Aug 9 - 16, 2025 now $2,499/wk* plus fees & taxes Aug 16- 23, 2025 now $2,499/wk* plus fees & taxesSirenia Cove is as good as new and ready to receive you! The pool is heated and the hot tub bubbling!Many new items not shown in photos;- ...

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Featured review

"Such a perfect place for our entire family"

We loved our time at Sirena Cove. There were so many amenities and room for all of our adult children, their spouses and our grandchildren all under the age of four. The pool was great fun and we enjoyed ...

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