Vacation Rentals & Beach Rentals in Anna Maria Island

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164 beach rentals

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“Anniversary Trip” Had a wonderful time at LA Siesta Condominiums for our anniversary vacation. Beautifully furnished and do close to the best beach in the USA

Match: Table tennis Wheelchair accessible

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Price per night from

$245

Land's End: Gulf-front Luxury, WIFI, HDTV

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$393

*** Isla Del Sol Paradise ***

St. Pete Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$172

Luxurious Beachfront Condo at Redington Towers

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$344

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

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Price per night from

$117

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$115

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$172

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Peace and Quiet in Gated Community on Boca Ciega Bay

Gulfport apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$77

4 Minutes From Beach, Beds for 6!

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$105

Gulfport Waterfront Mid-Century Modern Masterpiece

Gulfport house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$367

3 Bed/2 Bath Handicap Madeira Beach Gulf side Condo w/ Heated pool and Spa

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$344

TROPICCAL, 4 min from the beaches! Meticulously cleaned and sanitized!

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

“Lovely home in an awesome location!” Literally a minute's drive from the beach, this very clean and welcoming home is also convenient to great restaurants and shopping opportunities. It really is in a perfect location, especially considering the affordable price. Walking to restaurants and a rental shop is easy thanks to the sidewalk on Cortes. We even enjoyed a morning run to the beach - biking to the beach would also be a great option (3.5 mi one way.) The home might appear small at first, but we fit 6 comfortably, including 4 teenagers! The best part is the lovely décor that greets you after a long day at the beach or running around. Two thumbs up!

Responds fast! avg. 2 hours 28 minutes

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$144

Lovely one story home on the water

Palmetto house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$458

2 MINUTE WALK TO SIESTA BEACH!! (really) 1 MINUTE TO POOL. GREAT VALUE!!!

Siesta Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Happy Customer” We had an amazing time. The owners were so nice & made us feel so welcomed. I couldnt have been happier with our stay & we look forward to staying there again soon when life slows back down. Highly recommend this home♡

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$258

Condo on the Key

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Immaculate” I had a wonderful stay at the condo in the key. Robin was easy to work with and always responsive. The condo was very clean and well stocked. If you are looking for a place where you can lay back and relax this is a nice condo. I loved that it's in a gated area.

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$206

St.Armands Circle condo ( Kingston Arms )

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 3 hours 25 minutes

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$258

Oceanfront 1400 sq ft Condo at Beach Cottage One! Private Beach, Big Pool

Indian Shores apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“We had a great vacation at this condo.” My family has been visiting indian rocks beach for nearly two decades, and we continue coming back to this resort and specifically, Martin's condo. It is always kept updated and we had a nice relaxing stay. It has WiFi for the kids and has a picture perfect view of the beach, ocean, sunsets and pool deck. You won't be disappointed.

Responds fast! avg. 2 hours 11 minutes

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$245

502 Beach Place top floor condo view of bridge, water/John's Pass

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$378

Beach Front Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$447

White Sand Beaches- Bayfront Park

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$630

Unit #112 Sand Cay Beach Resort Pool and Garden View

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$278

Madeira Bay Resort 606

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$228

Madeira Bay Resort 402

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

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Price per night from

$137

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: Table tennis, Wheelchair accessible

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Price per night from

$201

Updated! Just Steps to the Sand! Cable, Wi-Fi, BBQ, Onsite Laundry Room & Parkin

North Redington Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 48 minutes

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$119

Come join us for your Winter Migration!!!!!!!!!!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$103

Direct Beachfront Unobstructed Ocean View Feet on White Sand Condo With Pool

Madeira Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$344

Fine Waterfront Living . Steps to Beach

St. Pete Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$487

Amazing Beachfront Condo, Siesta Key,

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$344

FANTASTIC VACATION! STEPS FROM THE POOL AND BEACH, VERY CLEAN CONDO!

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$271

New 6 Bedroom, Luxury Home in Gated Community

Siesta Key house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$999

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$284

Redington Towers 1 Beachfront 2 Bedroom Condo

Redington Shores condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$218

Charming 1 Bedroom Condo on Gulf of Mexico Beach

Indian Shores condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$287

Family friendly condo on the beach - Ocean Sands

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$158

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Best home away from home at the beach.” I spent a lot of time searching for a bungalow at the beach and my expectations were surpassed when I opened the door! The owners were thoughtful in design, layout and furnishings to provide a laid back experience at the beach. I wished I could have stayed forever - it was that nice. I especially enjoyed the fully stocked kitchen which included colorful dishes to match the colorful walls and great blue floor! Best of all - location - you can walk everywhere as you are right in the historic Bridge Street neighborhood.

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$245

Reserve now! Beautiful Siesta key Beach

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$344

Luxury Water Front Condo - Intercoastal Waterway

Treasure Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Exceptional” We just returned from a 4 week stay at another/similar condo in this same building, same owner. The unit was clean, comfortable, spacious and located in close proximity to everything we needed (i.e. Beach, supermarket, restaurants, shops). John (owner) was more than accomodating with helping us get online (wifi) and being flexible with our schedule. The Gulf view was great and the building was relatively quiet considering it was Spring Break month. Will definitely be returning.

1 of 2 match: Table tennis, Wheelchair accessible

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Price per night from

$240

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