Vacation Rentals & Beach Rentals in Anna Maria Island

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224 beach rentals

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Car not required

All filters match

Price per night from

$161

ROYAL REXHOST RESORTS – Madeira Beach Yacht Club (MBYCC)

Madeira Beach house

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Match: Children's pool Car not required

All filters match

Price per night from

$172

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Beach Dreams -"Dream Away Villa"

Anna Maria Island cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$338

Island Village Hideaway! Steps to Sand

Longboat Key house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$330

Spacious Apt. #1 Historic Walkable Downtown, between Siesta & Lido Beach

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$482

Beach Dreams " Sweet Dreams Villa"

Anna Maria Island villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$516

Beach Dreams "Tangerine Dreams Villa "

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$344

X Alice's Beach Bungalows 2 bdrm 500' to Beach!

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Loved it” Quiet but close to what ever you want. The beach is just across the road, one restaurant within walking distance, the main road to mainland is 1.2 miles away, but everything you need is on Gulf Blvd. The house and yard were well maintained. Inside was excellent shape with open floor plan that gave a sense of a large space. The kitchen was open and had about everything you would need including basic supplies like coffee, sugar, some spices, etc. We had arrived 1/2 hr early and cleaning lady was there so we went across the bridge to Johns Pass about a 1/4 mi and had a drink and came back as she was leaving to get a new microwave as it had broken when she checked it. There is a large back yard and private sitting area. The hot tub is in backyard along with a grill. The bedrooms were large with plenty of closet space. The bath room was roomy with a " sunken tub" that consisted of one step down for a seat and another step to the bottom for about 6-8 inches of water. However the shower was more that adequate. A really nice, comfortable place to stay for a few days.

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$373

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.

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$171

Piece of Paradise on Beautiful Anna Maria Island VRC 20-000087

Holmes Beach villa

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$148

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: Children's pool, Car not required

1 of 2 filters match

Price per night from

$166

Paradise Lane- Dolphin View on the Intercoastal Water !! Boats Welcome

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$343

Crystal Sands Unit 308 Siesta Key, Florida

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great Vacation Rental” We have been coming to Siesta Key for our Vacations for years... We have stayed at a number of Units at Crystal Sands, Crescent arms and El Presidente... Crystal Sands Unit 308 is one of the best Units we have stayed at... It has a great view of the Beach and Pool... You can watch the Sunsets and Moonsets right from the Lanai... The Unit is Roomy, Clean and had all the appliances, Dishes and Linens we needed... The Washer\Dryer in the Unit is very convenient... It has a New 60" Hdtv in the Living Room with an incredible picture... Jim left printed instructions for the Hdtv, Washer and Dryer which made it very easy to use the appliances in the Unit... We are looking forward to staying in Crystal Sands Unit 308 again for our next trip to Siesta Key...

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$430

Stunning & Serene +++ Minutes from Anna Maria Island, IMG Academy and more!

Bradenton apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 9 minutes

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$114

SunWay Suites Unit 2 Plover

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$23

Downtown Apartment in Historic Burns Square downtown Sarasota

Sarasota apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$281

Castnetter Beach Resort 2

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$315

King size Bed room 7

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$344

Island Hideaway! Bermuda-esque Guest House! Steps to the Sand!

Longboat Key guest house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$141

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 2 hours 31 minutes

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$344

Jamaica Royal Villas - Villa 42; by Beachside Management

Siesta Key condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$240

Hibiscus at The Wildflower

Siesta Key apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$489

Close to everything. w/2 Bikes

St. Petersburg house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$91

Remodeled Sunset Vistas 303N - Booking for Summer 2021, with No Cleaning Fees!

Treasure Island house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Children's pool

1 of 2 filters match

Price per night from

$258

1 of 2 match: Car not required, Children's pool

1 of 2 filters match

Price per night from

$573

CFP! St.PeteBeach Rental for 4! 01/09-11/2017. College Football Nat'l Champs

St. Pete Beach studio

  • Studio
  • 1 bathroom
  • sleeps 4

1 of 2 match: Car not required, Children's pool

1 of 2 filters match

Price per night from

$573

Your Hidden Private Gem "La Playa Azul"

Gulfport condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Car not required, Children's pool

1 of 2 filters match

Price per night from

$212

"Lovers Den" Your Hidden Private Gem

Gulfport condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Car not required, Children's pool

1 of 2 filters match

Price per night from

$149

Castnetter Beach Resort 5

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Children's pool, Car not required

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: Children's pool, Car not required

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: Children's pool, Car not required

1 of 2 filters match

Price per night from

$201

ADORABLE BEACH CONDO!!! GREAT RATES!!! FABULOUS SUNSETS ON ST. PETE BEACH!!!

St. Pete Beach condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$137

Enjoy our Beach, Pool and Dock! 100 5-Star Reviews!

Anna Maria house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$744

“Clean comfortable Siesta Key Condo with all the comforts of home...Perfect!” The condo is walking distance to shops, restaurants and quaint local tiki bar! The beach is a short walk across the street and through the beach-front section of the complex with lounge chairs and umbrellas available, very nice! I didn't mention the 2 pools (one beachside) and nice gym facilities also just downstairs of the unit. The covered parking space was an added plus! The condo was clean and very comfortable with all of the amenities of home which is greatly appreciated! You can even enjoy the view of the bayside inlet and beautiful landscaping from the kitchen through the entire wall of glass doors in the living/dining room! We had a wonderful week! The property owner Vic supplied more than enough information on the condo, local businesses and area maps! He was such a pleasure to work with! Thanks again Vic! We are already planning our next trip to Siesta Key in May!!

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$144

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$332

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: Children's pool, Car not required

1 of 2 filters match

Price per night from

$258

Cathy's Crescent Condos-Siesta Key, FL GULF FRONT

Siesta Key apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

“Great View” We stayed at Kathy’s condo during the 4th of July week. The Condo was great and the view was amazing. We enjoyed the fireworks display and easy access to the beach. We look forward to renting her condo again in the future.

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$314

Steps to beach and bay on beautiful Anna Maria Island

Bradenton Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Children's pool, Car not required

1 of 2 filters match

Price per night from

$101

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