Vacation Rentals & Beach Rentals in Anna Maria Island

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

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Smoking allowed

All filters match

Price per night from

$172

Royal Heir: Central 2BR Apt, 10 mins to DTSP pet friendly

Pinellas Park apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (unheated) Smoking allowed

All filters match

Price per night from

$201

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Tortuga Shoals

Tierra Verde townhouse

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$99

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: Smoking allowed, 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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$109

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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$210

19th Hole: Luxe 4/2 Stay W Pool and Mini Golf Course, 5 Mins to St. Pete Beach

South Pasadena house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$689

The Hideaway: 4/2 W Heated Pool and Outdoor Spaces, 10 mins to Sarasota Beach

Gulf Gate Estates house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$373

Blue Heron Inn: 1/1 Spacious Apartment, 15 mins to beaches, pet friendly

Oneco apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$127

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$259

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$316

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$172

Lady Palm Apt: 1/1 with 2 beds, garden vibes and outdoor spaces! Pet friendly

Bradenton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$144

Delightful Oasis #2

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$178

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: Smoking allowed, 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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$115

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: Smoking allowed, 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 40 minutes

1 of 2 match: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$119

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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$366

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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$92

Beach Dreams - Beach Cottage 2103

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great unit, perfect location” Been coming to Beach Cottage for over ten years and love the decor and location of Beach Cottage 2103. Indian Shores Vacation is the only place we think of for summer beach vacation.

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$436

The blu door spot in st.pete

Pinellas Park house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$97

House of Blues - Lovely 2-Bedroom Condo with Pool, W&D and Patio

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$201

Private Waterfront Home, Resort & Marina Sleeps 18

Madeira Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 18

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$153

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$158

Mansion away from home

St. Petersburg house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Responds fast! avg. 1 hour 32 minutes

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$459

Deluxe Queen Suite in Gorgeous Pop Art Gallery Pool Home Close to Everything!

St. Petersburg private room

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared outdoor pool (unheated), Smoking allowed

1 of 2 filters match

Price per night from

$144

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: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$161

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: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, 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: Smoking allowed, Shared outdoor pool (unheated)

1 of 2 filters match

Price per night from

$155

Viewing 38 of 504
rentals in Anna Maria Island

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