Vacation Rentals & Beach Rentals in Anna Maria Island

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377 beach rentals

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WESTGATE LAKES RESORT & SPA-Orlando Studio

Orlando apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 55 minutes

Match: Boat available Wheelchair adapted

All filters match

Price per night from

$129

Christmas Week Condo/ Next to Disney/ Dates Flexible/ River Island location

Kissimmee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Boat available Wheelchair adapted

All filters match

Price per night from

$196

These homes match some but not all of your filters. Clear all filters

villanirvana

Kissimmee villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Family trip” This was a wonderful trip and the house was magnificent. My family felt very at home and the pool was wonderful after a long hot day at the park.

Responds fast! avg. 3 hours 6 minutes

1 of 2 match: Boat available, Wheelchair adapted

1 of 2 filters match

Price per night from

$173

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

1 of 2 match: Boat available, Wheelchair adapted

1 of 2 filters match

Price per night from

$286

Vanderbilt Beach

Naples house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 33 minutes

1 of 2 match: Boat available, Wheelchair adapted

1 of 2 filters match

Price per night from

$73

Marriott Grande Vista Resort and SPA

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Boat available, Wheelchair adapted

1 of 2 filters match

Price per night from

$295

Studio Vacation Villa

Kissimmee villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$172

Family-Friendly Condo Minutes from Theme Parks w/ Resort Waterpark & Mini Golf

Four Corners house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$130

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$200

Lakeside Resort Condo Just 2 Miles From Disney w/ WiFi, Fireplace & More

Celebration house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$122

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$102

Beautiful Large Studio Condo on the Lake

Orlando apartment

  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$228

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$430

Waterfront Condo with Boat

Key Largo apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$441

Weeki Wachee main river .Not a canal ,walk to Rogers park beach

Weeki Wachee house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$315

Luxury 2BR Suite at Vacation Village at Weston

Weston hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 15 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$1,145

Anna Maria Island Beach Haven

Cortez house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$1,500

Cottage Haven-One Minute Walk To The Beach-Private Yards-Keyless Locks

Cortez cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$211

AMI Lighthouse Cottage-One Minute Walk To The Beach-Keyless Locks

Cortez cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$164

Entire Guest House- Sunset Hide A Way

Naples house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 22 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$594

Renzzi Wynwood Apartments

Miami apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$229

Anna Maria Island Beach Watch

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$250

Anna Maria Island Beach Happy-Direct Beach Front-1BR-1BR

Bradenton Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$228

The Caribbean Resort - Fish Tail Palm

Matecumbe Key house

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$573

1BR w/ WiFi, Lake Access, Resort Pool, Only 3 Miles From Disney!

Celebration house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$81

The Caribbean Resort - Canary Island Palm North

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$630

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$122

The Caribbean Resort - Royal Palm North

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Jamaican Palm House

Matecumbe Key cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$1,088

The Caribbean Resort - Hemingway House South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Canary Island Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$630

The Caribbean Resort - Royal Palm South

Matecumbe Key house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$1,432

The Caribbean Resort - Princess Palm South

Matecumbe Key house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$630

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$132

The Caribbean Resort - Malayan Palm North

Matecumbe Key house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$630

Family-Friendly 1BR Minutes from Theme Parks w/ Resort Waterpark & Mini Golf

Four Corners house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$90

Lovely Condo Just 1 Mile From Disney w/ Resort Pool, WiFi & More

Celebration house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$91

The Caribbean Resort - Bird of Paradise - One Bedroom One Bath

Matecumbe Key house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 27 minutes

1 of 2 match: Wheelchair adapted, Boat available

1 of 2 filters match

Price per night from

$573

Viewing 38 of 377
rentals in Anna Maria Island

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