Vacation Rentals & Beach Rentals in Anna Maria Island

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41 beach rentals

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$101

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

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$103

Direct Beachfront 2 BR Condo on Florida’S Beautiful Gulf Coast!

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$430

AMI Beach Front Condo - heated pool and less than 50 steps to the Beach!

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Walk to Beach, private condo with pool

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$258

Limefish

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$2,061

Beach Bliss

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$1,145

Hibiscus Hideaway B - Top Floor Unit

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 39 minutes

1 of 2 match: Shared outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$283

Anna Maria Island Runaway Tropical Dream-One Minute Walk To The Beach-Heated Poo

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 3 hours 20 minutes

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$213

SPECIAL! $650 8/24 - 8/31. PRIME LOCATION AMI DIRECTLY ON BEACH HEATED POOL

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$315

Castnetter Beach Resort 6

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$315

GULF COAST DESTINATION

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$201

Lifestyle on the island

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Anna Maria Island Vacation Rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Island Paradise” The moment we arrived, exhausted after many delays and problems, the Thomas' home became our home. The condo is well appointed, with comfortable beds, a wonderful kitchen and a fully stocked linen closet, right down to beach towels. Laine, Kevin and Howard are so responsive and saw to all of our needs. Location was prime. We walked to get groceries, eat and do other shopping. There were 7 miles of beaches to explore and the quaint villages of anna Maria and Cortez and Bridge Street kept us occupied when we weren't soaking up the sun. The lanai was my favorite place to drink my coffee and check out the action at the pool each morning . We ate the majority of our meals there, under the twinkling lights. It was a wonderful month!

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$166

Blue Bayou

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Home away From Home” I've been staying at the Graham's condo once or twice a year for the last 9 years or more. It's always been pristine clean. Accomodations are the best. Rooms large and bright and fully equipped. Decor is so welcoming. Location is the best. Only decisions to make are beach or pool, and where to eat tonight! I consider it my "home away from home." You won't be disappointed, and the value cannot be beat. Don't hesitate to book your reservation.

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$172

Runaway Bay - Bradenton Beach - Bay View Unit 193

Anna Maria Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Home away from home” This place is an incredible value. It's spacious and comfortable, and we felt right at home. Sarasota Bay is just steps from the back patio, and it's so lovely to sit outside and watch water--so many fish, dolphins, and birds right there. Everything was in good working order and clean upon our arrival. The beach is a quick walk across the street from the complex, and we spent a lot of time at the heated pool. We would love to rent this unit again! PERFECT LOCATION.

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$209

Gulf Beach Place, miles of whites sandy beach

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$287

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

Bradenton Beach apartment

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really impressed with how many little things were available. There were plenty of towels, soap and shampoo dispensers in the bathroom, spices in the cabinet, beach towels, and even aloe gel for burns. In the garage there is an area full of sand toys and floats and a grill. We felt so comfortable and had a true vacation.

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$401

Bermuda Bay Club Un09 Special discount for February price reduced last minute

Bradenton Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Excellent accomodation and locality” This is the second time we have stayed here, in different units. Everything was excellent. No fuss, and just so convenient with the trolley at the roadside and the beach a walk across the road

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Anna Maria The Pink Flamingo

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 1 hour 41 minutes

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$458

Great Townhouse Very Close to the Beach, Shops, and Restaurants

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$344

Runaway Bay unit 192 bay view 2bed/2Bath - Bradenton Beach - Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$194

Cheers to this 2 BR Gulf-front/Intercoastal Endless Summer Beach Retreat!

Bradenton Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 52 minutes

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$352

Rambo's Beach Retreat! Tradewinds Unit 14

Bradenton Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Games room, Shared outdoor pool (heated)

1 of 2 filters match

Price per night from

$453

Family Reunion Villa on Anna Maria Island, Florida

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 of 2 match: Shared outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$573

Mintfish

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$1,145

Newly renovated beach house near AMI free trolley stop with Private pool

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Shared outdoor pool (heated), Games room

1 of 2 filters match

Price per night from

$561

Great rentals within 20 miles that match your search

Beautiful Island on Boca Ciega Bay & The Beach

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$115

Panoramic Ocean Views 2

St. Petersburg apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Great place to stay” I stayed in this condo last February. It is calm, bright and perfectly clean. The balcony and the view on the water are outstanding! In addition to that, Sabina is perfectly organized, answered all the question I had and made sure I was feeling perfect. I definitely recommand it!

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$201

LUXURY WATERFRONT CONDO ON ISLA DEL SOL/St.Pete's

St. Petersburg condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$430

River Strand Golf and Country Club Resort

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$229

River Strand Luxury Condo-Tennis & Golf Community

Bradenton condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$86

REDUCED FOR APRIL!

Madeira Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“get away” My experience was kinda shaky at first , I was given the wrong gate code to get in complex, plus there were a couple of wristbands for pool entry missing and a blind that was messed up,but was able to be fixed in about 15 minutes. Our reservations were never given to property managers at office as well, but as soon as Jennifer responded she was able to take care of that. I have been to 2 other units there and this unit is the most modern by far and is very clean,and a great spot in the complex.

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$171

Florida Ocean Front Condo

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$622

Seaplace Condo - 1975 GMD 104

Longboat Key condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$192

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$172

Swanky Starfish

St. Petersburg condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Shared outdoor pool (heated) Games room

All filters match

Price per night from

$126

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rentals in Anna Maria Island

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