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Vacation rental beach houses in Anna Maria

Vacation rental beach houses in Anna Maria

Book beachfront vacation rental houses, cottages, and more on Airbnb

Top-rated houses in Anna Maria

Guests agree: these stays are highly rated for location, cleanliness, and more.

5 Star Property!  Spring-Summer ‘21 Limited Avail.
SUPERHOST
Entire house · 8 guests · 5 beds · 2 baths

5 Star Property! Spring-Summer ‘21 Limited Avail.* It doesn't get much better than being right on the water, located on a wide canal, and ½ block from the beach. * Enjoy the large 16' x 30' private pool in a picturesque tropical landscape along with a 30' fishing/boat dock. * Within walking distance of Pine Avenue, City Pier, Two Scoops, Waterfront Restaurant, Galati's Marina, and Island Ocean Star Restaurant. * There's no better way to unwind and forget all your troubles, than staying at Sunshine Cottage, located in the City of Anna Maria!

Cozy Beachhouse 800 steps to beach
SUPERHOST
Entire house · 3 guests · 1 bed · 1 bath

Cozy Beachhouse 800 steps to beachThis beautiful home is only 800 steps from one of the most beautiful beaches in Southwest Florida. Great getaway for couples. Amazing restaurants and entertainment very close. Free trolley, endless things to do: kayaking, sunbathing, and relaxing.

Luxury 3BR/3BA, Private Heated Pool, Beach
SUPERHOST
Entire house · 6 guests · 5 beds · 3 baths

Luxury 3BR/3BA, Private Heated Pool, BeachRenovated and professionally decorated single family home that sleeps 8. 3 bedrooms and 3 full bathrooms. Living room with pullout couch as well as games, books and movie library. Luxurious heated pool with waterfall and Tiki table in private tropical backyard. Large covered lanai with TV, mini-fridge, granite counter for food preparation and gas BBQ. Large size Washer/Dryer. 4 minute easy stroll to beach. Attached garage. Low traffic street. Tons of toys as well as pool and beach supplies.

Vacation rentals for every style

Get the amount of space that is right for you

  • Houses
  • Cottages
  • Apartments

Popular house amenities in Anna Maria

  • Pool
  • Pets allowed
  • Air conditioning
  • Kitchen
  • Wifi

Cottages in Anna Maria

Turtle Cottage - Anna Maria Island
SUPERHOSTEntire cottage
Turtle Cottage - Anna Maria Island
Price:ﺩ.ﺇ703 / night
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
SUPERHOSTEntire cottage
Adorable Pine Ave Cottage ❤️Walk to Beach and Bay!
Price:ﺩ.ﺇ648 / night
NEW LISTING! Sailfish Gulf Suites #4, Garden Views, Steps from the Beach
Entire cottage
NEW LISTING! Sailfish Gulf Suites #4, Garden Views, Steps from the Beach
Price:ﺩ.ﺇ551 / night
'Elegance' 100 Steps from the Beach
Entire cottage
'Elegance' 100 Steps from the Beach
Price:ﺩ.ﺇ1,157 / night
Harrington Bungalow 5 in the Heart of Anna Maria Island
Entire cottage
Harrington Bungalow 5 in the Heart of Anna Maria Island
Price:ﺩ.ﺇ533 / night
Becker's Beach Bungalow
SUPERHOSTEntire cottage
Becker's Beach Bungalow
Price:ﺩ.ﺇ530 / night
Palm Cottage in North Longboat Key
Entire cottage
Palm Cottage in North Longboat Key
Price:ﺩ.ﺇ312 / night
50 Steps to Beach🏖.  Hot Tub! 1bd modern cottage🏝
SUPERHOSTEntire cottage
50 Steps to Beach🏖. Hot Tub! 1bd modern cottage🏝
Price:ﺩ.ﺇ1,005 / night
Bay Breeze Cottages #2
SUPERHOSTEntire cottage
Bay Breeze Cottages #2
Price:ﺩ.ﺇ941 / night
MorSea Cottage: A Beachside Oasis
Entire cottage
MorSea Cottage: A Beachside Oasis
Price:ﺩ.ﺇ1,157 / night
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!
Entire cottage
Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!
Price:ﺩ.ﺇ845 / night
Whitney Beach Cottage your tropical escape.
Entire cottage
Whitney Beach Cottage your tropical escape.
Price:ﺩ.ﺇ275 / night
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Pet-friendly houses

Anna Maria Island Duplex w/ private pool (side B)
SUPERHOSTEntire house
Anna Maria Island Duplex w/ private pool (side B)
Price:ﺩ.ﺇ882 / night
Beachfront Private Beach, Dogs ok, Backyard beach
Entire house
Beachfront Private Beach, Dogs ok, Backyard beach
Price:ﺩ.ﺇ1,285 / night
Dog-friendly home w/heated private pool, near beach, shopping, dining
Entire house
Dog-friendly home w/heated private pool, near beach, shopping, dining
Price:ﺩ.ﺇ815 / night
The Sandbox
Entire house
The Sandbox
Price:ﺩ.ﺇ1,117 / night
Upscale Home 2 blocks to beach! Private Pool +Tiki
SUPERHOSTEntire house
Upscale Home 2 blocks to beach! Private Pool +Tiki
Price:ﺩ.ﺇ1,028 / night
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
SUPERHOSTEntire house
5 STARS! Tropical Salt H2O Pool, Steps to BEACH!!
Price:ﺩ.ﺇ1,194 / night
AMI Boathouse
SUPERHOSTEntire house
AMI Boathouse
Price:ﺩ.ﺇ1,759 / night
AMI Retreat
SUPERHOSTEntire house
AMI Retreat
Price:ﺩ.ﺇ1,388 / night
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️ Seaside Sanctuary ⭐️ fischervacationrentals
Price:ﺩ.ﺇ731 / night
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
SUPERHOSTEntire house
⭐️Escape to Anna Maria ⭐️ fischervacationrentals
Price:ﺩ.ﺇ731 / night
The Anna Maria Beach Cottage - East
SUPERHOSTEntire house
The Anna Maria Beach Cottage - East
Price:ﺩ.ﺇ557 / night
Top-rated Anna Maria, Florida Vacation Rental
SUPERHOSTEntire house
Top-rated Anna Maria, Florida Vacation Rental
Price:ﺩ.ﺇ1,131 / night
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Houses with pools

Golf cart +4bd/2b w large outdoor pool/shower/deck
SUPERHOSTEntire house
Golf cart +4bd/2b w large outdoor pool/shower/deck
Price:ﺩ.ﺇ1,784 / night
Spectacular home 700 feet from the beach!
SUPERHOSTEntire house
Spectacular home 700 feet from the beach!
Price:ﺩ.ﺇ663 / night
Captain's Quarters at Spinnakers Vacation Cottages
SUPERHOSTEntire house
Captain's Quarters at Spinnakers Vacation Cottages
Price:ﺩ.ﺇ1,138 / night
North Island Beach Escape
Entire house
North Island Beach Escape
Price:ﺩ.ﺇ819 / night
Walk 2 Beach + PRIVATE Pool with TIKI + Golf Cart
SUPERHOSTEntire house
Walk 2 Beach + PRIVATE Pool with TIKI + Golf Cart
Price:ﺩ.ﺇ1,194 / night
Anna Cabana B
SUPERHOSTEntire house
Anna Cabana B
Price:ﺩ.ﺇ590 / night
Laid-back beach escape w/ heated private pool, screened lanai, Ping-Pong, more!
Entire house
Laid-back beach escape w/ heated private pool, screened lanai, Ping-Pong, more!
Price:ﺩ.ﺇ801 / night
Beachfront Oasis - Elegant beach front home! Views for days, private pool, beach access!
Entire house
Beachfront Oasis - Elegant beach front home! Views for days, private pool, beach access!
Price:ﺩ.ﺇ1,807 / night
Exquisite Private Pool  Elevator Beach/Bay views
SUPERHOSTEntire house
Exquisite Private Pool Elevator Beach/Bay views
Price:ﺩ.ﺇ1,990 / night
Happy Island Cottage - Heated Pool
Entire house
Happy Island Cottage - Heated Pool
Price:ﺩ.ﺇ1,208 / night
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
SUPERHOSTEntire house
New Prof Decor-Pool/Spa 5 Mn walk 2 ocean Discount
Price:ﺩ.ﺇ1,675 / night
Salty Dogs Beach House -  Special Rate Dec 5 - 12!
SUPERHOSTEntire house
Salty Dogs Beach House - Special Rate Dec 5 - 12!
Price:ﺩ.ﺇ1,418 / night
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