Vacation Rentals & Beach Rentals in Anna Maria Island

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500 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Shared outdoor pool (unheated)

All filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Shared outdoor pool (unheated)

All filters match

Price per night from

$173

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Shared outdoor pool (unheated)

All filters match

Price per night from

$173

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

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$575

CFP! St.PeteBeach Rental for 4! 01/09-11/2017. College Football Nat'l Champs

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$575

Remodeled Sunset Vistas 303N - Booking for Summer 2021, with No Cleaning Fees!

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$259

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$150

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$212

Anna Maria Islands best location Heated pool Best prices!

Anna Maria Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$863

Siesta Key Beach Cottages on Crescent

Siesta Key cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$225

Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$414

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$210

Bay Mariner - Gorgeous water front condo!

Tallevast studio

  • Studio
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Children's pool, 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: Children's pool, 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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$158

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$98

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$283

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$119

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$366

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), Children's pool

1 of 2 filters match

Price per night from

$478

Grand accomdation on USA #1 Beach - Siesta Key Fl

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$206

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$192

*** SUPER SPECIAL RATES at Harbor Towers ***

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 56 minutes

1 of 2 match: Shared outdoor pool (unheated), Children's pool

1 of 2 filters match

Price per night from

$114

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$266

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$96

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$173

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$156

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$147

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$123

Ocean Sands 504 Beachfront Studio Condo

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 50 minutes

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$131

Backyard Tiny House Oasis!

St. Petersburg guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$101

Hibiscus Hideaway Condo Walk to Historic Bridge St

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Children's pool, 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 39 minutes

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$537

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: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$178

Front Row Seat to World Class Sunsets. Beachfront and Across from Johns Pass Vi

Madeira Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$189

Waterfront Picnic Area, Fishing Dock, Solar Heated Pool, Across from Beach. Comf

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 3 minutes

1 of 2 match: Children's pool, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

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rentals in Anna Maria Island

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