Vacation Rentals & Beach Rentals in Anna Maria Island

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546 beach rentals

Amazing views, 11th flr, On the beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (unheated) Housekeeping Included

All filters match

Price per night from

$410

Perfecto's Suite #2

Bay Pines apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Match: Shared outdoor pool (unheated) Housekeeping Included

All filters match

Price per night from

$167

NSS Pattam, custom 84 foot traditional motor yacht downtown.

St. Petersburg yacht

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 42 minutes

Match: Shared outdoor pool (unheated) Housekeeping Included

All filters match

Price per night from

$1,376

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Housekeeping Included

All filters match

Price per night from

$172

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

Queen Bed Room at Palm Grove Inn Downtown St Pete

St. Petersburg hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$344

Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$413

Bay Mariner - Gorgeous water front condo!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$99

Steps from beach! Air-conditioned - shared pool

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Housekeeping Included, 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 39 minutes

1 of 2 match: Housekeeping Included, 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 39 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$210

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$287

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: Housekeeping Included, 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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

Casa Sea Esta Executive Studio / Condo at Sara Cay

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Housekeeping Included, 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 39 minutes

1 of 2 match: Housekeeping Included, 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 39 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$366

Blue Heron Studio / Condo 2 miles from Airport!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$119

NEW! Staying with friends or family? Ask them to rent you a GuestWing!

St. Petersburg caravan/mobile home

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$206

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$155

Tiny Treasure - Stunning waterfront condo with dock (102)

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 2 hours 7 minutes

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$229

Sarasota Waterfront and Marina Community with Tikki Bar and Grill

North Sarasota condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Housekeeping Included

1 of 2 filters match

Price per night from

$102

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: Housekeeping Included, 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: Housekeeping Included, 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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Housekeeping Included, 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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$172

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$155

Backyard Tiny House Oasis!

St. Petersburg guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$101

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$118

Ocean Sands 504 Beachfront Studio Condo

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$131

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$140

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$174

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: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$139

Responds fast! avg. 16 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$168

Responds fast! avg. 16 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$127

Responds fast! avg. 16 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$232

Exceptional Beachfront Location. Heated Pool. Expansive Private Corner Balcony!

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 minutes

1 of 2 match: Housekeeping Included, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$234

Viewing 38 of 546
rentals in Anna Maria Island

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