Vacation Rentals & Beach Rentals in Anna Maria Island

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492 beach rentals

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Climbing frame Shared outdoor pool (unheated)

All filters match

Price per night from

$172

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Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Shared outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$114

+++ Clean & Bright +++ Minutes to Anna Maria Island

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Shared outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$178

Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$413

Downtown Hideaway Close to all

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Bay Mariner - Gorgeous water front condo!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$99

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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$210

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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$158

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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$109

Cozy & Bright+++Minutes to Anna Maria Island, IMG Academy and more

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Shared outdoor pool (unheated), Climbing frame

1 of 2 filters match

Price per night from

$117

Guest House, 750 sq ft, private, with all amenities, parking and pool

St. Petersburg cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$98

2 bed Condo in peaceful Shorewalk. Close to IMG, Beaches, shops and restaurant

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$120

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 40 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

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: Climbing frame, 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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$366

Shorewalk waterfront Condo Bradenton

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Nice and affordable condo convenient to shopping and restaurants.” This unit has been updated and is a very comfortable place to stay. The owner responded promptly when we contacted him.

Responds fast! avg. 2 hours 1 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$96

Madeira Towers 302 Beachfront 3 bedroom 2 bath at Madeira Towers

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 50 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$388

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

Serendipity Apt: 10 mins to DTSP 1/1 w/ pull out sofa bed, pet friendly

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

The Jitterbug Apt: Central 1 bedroom w pullout bed, 10 mins to DTSP pet friendly

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

Backyard Tiny House Oasis!

St. Petersburg guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$101

Madeira Towers 601 Beach front with spectacular views

Madeira Beach apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Everything you expect and more” Without a doubt I'd stay there again, we've always stayed on Madeira Beach for the last 12 visits to Florida and this is the best condo we've stayed in, excellent value for money. Very clean and quiet , very well equipped, new carpets and new kitchen floor tiles , the caretaker was brilliant , polite and helpful , I really took to him , I had great conversations with him about fishing. The condo is positioned very well to all amenities and because all entrances needed keys you felt very secure ,, this is the place for me , when we visit again this will be the first condo I will look for availability ,,,and I guess a lot of renters have done as when I looked it's booked up to May 2017,, not surprised at all to be honest.

Responds fast! avg. 50 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$140

Ocean Sands 504 Beachfront Studio Condo

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$131

The Love Shack: 1/1 Apt for couples, shared retro pool space

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$155

Madeira Towers 802 Renovated Madeira Towers Beachfront 2 Bedroom 2 Bathroom Cond

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 50 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$118

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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$424

Responds fast! avg. 16 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$232

Responds fast! avg. 16 minutes

1 of 2 match: Climbing frame, 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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$174

Responds fast! avg. 16 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$168

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: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Responds fast! avg. 3 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$132

Responds fast! avg. 3 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$132

Spectacular Gulf Front Building. Heated Pool and Spa. Great Location. Corner Uni

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$275

Corner Unit Directly on a Quiet and Private Section of Sunset Beach with an Awes

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$228

The Ultimate Florida Getaway! Picture Perfect Views, Furnishings and Location.

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Climbing frame, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$166

Viewing 38 of 492
rentals in Anna Maria Island

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