Vacation Rentals & Beach Rentals in Anna Maria Island

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1,008 beach rentals

Monthly Rental, 2 bed, 2 bath, Ocean view.

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Clothes dryer Shared indoor pool

All filters match

Price per night from

$115

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Clothes dryer Shared indoor pool

All filters match

Price per night from

$172

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ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

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: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$172

LaPlaya 106A-Beach front! Steps to the white sand and turquoise Gulf of Mexico.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$376

LaPlaya 104A- Gulf front! Walk right from your lanai onto the private beach.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$311

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$221

LaPlaya 107A-Soak up the sun or float in the warm Gulf waters.

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$311

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$376

LaPlaya 205D-Spectacular sunsets from your private Gulf-front lanai or sundeck.

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 101E-Relax on your private lanai under the palms!

Longboat Key condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$276

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 204D-Beach-lovers paradise! 200 feet of private beach

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$414

LaPlaya 102B-Directly on the beach with the warm Gulf waters waiting!

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Clothes dryer, Shared indoor pool

1 of 2 filters match

Price per night from

$339

203 PERIWINKLE - PRETTY PALMS

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$553

A Gulf Front Paradise ! Newly updated , wide open wall to wall view, spacious cl

Bradenton Beach condo

  • 2 bedrooms
  • 4 bathrooms
  • sleeps 8

Responds fast! avg. 16 minutes

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$458

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$218

Beautiful, Affordable Close to famous Siesta Beach

Siesta Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“It was wonderful!” Everything about the trip and condo was great! Mike met us to give us the keys and we called him for suggestions about restaurants, etc. and he was very helpful. The condo was very clean and had everything we needed. It was also great that we were able to use the beach chairs and umbrella. I am already trying to figure out when we can go again.

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$163

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: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$241

Beachside Efficiency in Treasure Island (Blue)

Treasure Island apartment

  • 1 bathroom
  • sleeps 2

“Perfect location” The location of this stay is just amazing for the price. It's not directly on the beach but it practically feels like it is because there it is less than one minute to get to the beach without crossing any major road. The place is small, but it worked perfectly for just 2 people. Doesn't have a stove or oven so you have to resort to fruits or microwave food but it's not a big deal as there are tons of restaurants nearby. Only issue we really had was that you could hear either the neighbors next door or the above us running around and banging but it wasn't for too long and wasn't too bad. We had ignored it pretty quickly if that helps. For longer stays, be sure to get toilet paper and possibly soap. Also there is no way to wash clothes so pack a lot if this is your only stay. I don't believe there was an outdoor shower to wash off the sand before going in, but honestly we could have just missed where it was. Overall, really nice place, can't beat the price for the location.

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$86

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$344

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: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$222

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: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$388

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$194

Beach condo

Longboat Key condo

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Clothes dryer

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: Shared indoor pool, Clothes dryer

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: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$230

AMAZING LOCATION ! direct across ST, from beach

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$167

Directly across the street from the beach ! Unit # 4

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$167

Directly across the street from the Beach ! Unit #3

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$167

New Listing PERFECT LOCATION ! Unit # 5

St. Pete Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$201

Sunset Beach Cottages, 1 Bedroom Beach Cottages

Treasure Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Responds fast! avg. 2 hours 3 minutes

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$241

🏝Paradise on the Sarasota Bay, Close to Gulf Beaches🏝 (Sarasota)

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$194

St Pete Beach fun in sun!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Clothes dryer

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: Shared indoor pool, Clothes dryer

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: Shared indoor pool, Clothes dryer

1 of 2 filters match

Price per night from

$122

Viewing 38 of 1,008
rentals in Anna Maria Island

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