Vacation Rentals & Beach Rentals in Anna Maria Island

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714 beach rentals

Luxury Penthouse Condo Overlooking Beach/Gulf

Treasure Island apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Review” The place was amazing! Perfect weather and a great week! Thank you so much for the opportunity! We had the best week!

Match: Ceiling Fans Wheelchair adapted

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Price per night from

$286

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4 Minutes From Beach, Beds for 6!

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$105

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$193

Fabulous Flamingo Cottage

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$161

Sunset Beach Paradise

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$60

SUNSET VISTA ON LONGBOAT KEY

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$287

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$258

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$287

Beautiful Beachfront Condo on the FL Gulf Coast

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful family beach vacation condo” The condominium is a great place to stay. All the amenities you need to enjoy a relaxing family vacation. There is an picturesque view of the beach on the balcony and a large pool to enjoy. The location of the condo is convenient to shopping and restaurants. Carol (the owner) is always very helpful and accessible if you have any questions about your stay. We have found a new place to stay on our summer vacation and can't wait to visit again next year!

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$241

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: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$96

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 33 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$144

Beachfront Madeira Beach - Across from Johns Pass!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$456

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$23

Kima 503 Madeira Beach Front 2bd/2bath Condo Top Floor WHITE SANDY BEACHES!

Madeira Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Wonderful !!!” I never know from the pictures posted when they were taken and the true condition of the home. With this property we were not disappointed. We took beach chairs, towels and all of that was provided at the house. The house was clean and just as pictured. The only thing that I can suggest is knife's for the kitchen. There are towels and lines galore. and the location was good. Close to all we wanted to do but quiet as we wanted it to be. The house has an apartment upstairs that we rented for our son and it worked out great. Plenty of room. No fighting for bathroom time to shower. There was 7 of us and we have already voted on this property for our next years trip to the beach...

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$222

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: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$206

Tiny House Siesta - Sand Dollar – A private master loft and open living space

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$448

Treasure Island Beach Duplex S

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$287

Beach condo

Longboat Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$516

Great location, quiet, peaceful, and comfortable

Sarasota house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$46

Sunset Beach One Bedroom Gulf View

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$230

Luxury Beach Condo built 2023

Madeira Beach condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$343

Turtle Heaven apartment by the beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$183

Flamingo Love Apartment by the beach

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$183

Dolphin Pod Apartment by the beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$183

Palm Haven on Treasure Island By the Beach

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$183

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: Wheelchair adapted, Ceiling Fans

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: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$172

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$155

The Coconut on St Pete Beach - private pool - walk to water and dining!

St. Pete Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$195

Beautiful Condo near Anna Maria Beaches & IMG Academy

South Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$123

Bromeliad at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$490

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$490

Pineapple at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$490

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$138

Starfish Bungalow 1B/1B 2 Min from Bay and Beach!

St. Pete Beach bungalow

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$459

Renovated 1BR Haven - 2 Mins from Sunset Beach!

Treasure Island house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$206

Cute 1 bedroom - 5 min Walk to Beach

Treasure Island apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$241

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

Madeira Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 10

1 of 2 match: Wheelchair adapted, Ceiling Fans

1 of 2 filters match

Price per night from

$379

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rentals in Anna Maria Island

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