Vacation Rentals & Beach Rentals in Anna Maria Island

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32 beach rentals

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

Longboat Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Bicycles available Shared outdoor pool (unheated)

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Price per night from

$742

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Steps from beach! Air-conditioned - shared pool

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$109

Steps from Beach! Grill - Wifi - By LoveRentals

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$158

Full Kitchen - Shared pool - By LoveRentals

Holmes Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$210

SAPPHIRE - HARBOR ISLE

Bradenton Beach townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$286

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: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$191

Anna Maria Island Sunshine Kiss Villa

Holmes Beach studio

  • Studio
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$151

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$283

Sunset Beach 101 Beach Front Unit

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$366

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: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$208

Songbird Cottage

Anna Maria Island cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$110

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 (unheated), Bicycles available

1 of 2 filters match

Price per night from

$514

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$628

Tripletail

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$1,712

Cloud 9

Anna Maria house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$1,940

Walk to the beach, from this remodeled condo! Pool, WIFI, restaurants, shopping

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 16 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Responds fast! avg. 16 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$127

Updated w/bay view , across from the beach , pool, elevator , close restaurants

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 16 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 16 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$168

Responds fast! avg. 16 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$232

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$298

Luxury waterfront home with a heated pool and spa!

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$537

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 (unheated), Bicycles available

1 of 2 filters match

Price per night from

$474

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$741

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$620

Waves on Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$970

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$451

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$1,141

Serendipity

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$1,260

Serendipity Deux- Beachfront 4 Bed/heated pool/elevator

Anna Maria house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Bicycles available

1 of 2 filters match

Price per night from

$2,290

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$156

Responds fast! avg. 3 hours 41 minutes

1 of 2 match: Bicycles available, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$170

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