Vacation Rentals & Beach Rentals in Anna Maria Island

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37 beach rentals

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Table tennis

All filters match

Price per night from

$623

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Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$430

2 bedroom Florida condo unit 13 at family friendly resort

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

1 bedroom single story condo near pool

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$295

2 bedroom poolside condo steps from ocean beach and dock on bay

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$426

1 bedroom single story ocean view

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$360

Walk to Beach, private condo with pool

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$258

AMI Beach Front Condo - heated pool and less than 50 steps to the Beach!

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Amazing Village Cottage! Walk to Whitney Beach!

Longboat Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$394

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,064

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,147

Longboat Key Cedars Beach House-Pet Friendly-2 Minute To The Beach

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$192

Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Poo

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$216

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$209

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$101

Beach front condo in Longboat Key

Longboat Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$430

Anna Maria Island Vacation Rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$167

Blue Bayou

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Home away From Home” I've been staying at the Graham's condo once or twice a year for the last 9 years or more. It's always been pristine clean. Accomodations are the best. Rooms large and bright and fully equipped. Decor is so welcoming. Location is the best. Only decisions to make are beach or pool, and where to eat tonight! I consider it my "home away from home." You won't be disappointed, and the value cannot be beat. Don't hesitate to book your reservation.

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$201

Castnetter Beach Resort 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$316

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$316

Bermuda Bay Club Un09 Special discount for February price reduced last minute

Bradenton Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Excellent accomodation and locality” This is the second time we have stayed here, in different units. Everything was excellent. No fuss, and just so convenient with the trolley at the roadside and the beach a walk across the road

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

Bradenton Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really impressed with how many little things were available. There were plenty of towels, soap and shampoo dispensers in the bathroom, spices in the cabinet, beach towels, and even aloe gel for burns. In the garage there is an area full of sand toys and floats and a grill. We felt so comfortable and had a true vacation.

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$401

Beautiful Longboat Key Home!

Bradenton Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 27 minutes

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$516

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$459

Runaway Bay unit 192 bay view 2bed/2Bath - Bradenton Beach - Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$194

Cheers to this 2 BR Gulf-front/Intercoastal Endless Summer Beach Retreat!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 52 minutes

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$352

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$453

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Perfect Luxury” Our 5-week stay at this vacation rental was absolutely perfect. The house was everything you could ask for and more. We have stayed in many vacation rentals in the last 20 or so years that we have been coming to anna Maria Island and I have to say this one was right at the top of the list. The kitchen was outfitted with everything you could want. The beds were very comfortable. The neighborhood was nice and quiet. Short walk to the beach. The owners were very nice to deal with and always responded quickly and were very warm and helpful. Definitely can recommend this vacation rental.

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$476

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$574

March 23-March 30, 2024 Springbreak 3bdr on the beach Longboat key

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$746

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$975

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Table tennis

1 of 2 filters match

Price per night from

$1,262

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