Vacation Rentals & Beach Rentals in Anna Maria Island

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1,127 beach rentals

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

Sarasota condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared indoor pool Linen provided

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: Shared indoor pool Linen provided

All filters match

Price per night from

$173

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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: Linen provided, 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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$173

LaPlaya 206C-Gorgeous vistas of the Gulf

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Linen provided, 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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$275

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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$376

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

Longboat Key condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$414

1 of 2 match: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$414

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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$339

1 of 2 match: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$220

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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$311

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: Linen provided, Shared indoor pool

1 of 2 filters match

Price per night from

$376

4 Minutes From Beach, Beds for 6!

St. Petersburg apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$105

Queen Bed Room at Palm Grove Inn Downtown St Pete

St. Petersburg hotel apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$345

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$332

Fabulous Flamingo Cottage

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Linen provided

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: Shared indoor pool, Linen provided

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$288

Gulfview front house

St. Pete Beach house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 8

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$184

Charming Private Studio in Historic Downtown Area

Sarasota studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$259

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$423

IDEAL LOCATION ! directly across st from the beach Unit # 6

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 0 minutes

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$167

The Country Inn: spacious 1 bedroom w sofa bed, shared pool centrally located

Pinellas Park apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$114

4 Bed 3bath Water front home

Sarasota house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$435

Pass-A-Grille Beach House

St. Pete Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$219

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$144

Newly Remodeled Spacious Loft in Sarasota!

Sarasota apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$296

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, Linen provided

1 of 2 filters match

Price per night from

$242

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, Linen provided

1 of 2 filters match

Price per night from

$87

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$345

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$23

SunWay Suites Unit 4 Pelican

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$138

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, Linen provided

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: Shared indoor pool, Linen provided

1 of 2 filters match

Price per night from

$206

Viewing 38 of 1,127
rentals in Anna Maria Island

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