Vacation Rentals & Beach Rentals in Anna Maria Island

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1,633 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: Fridge Wheelchair adapted

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Price per night from

$286

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Tropic Terrace #9 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #8 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$165

Tropic Terrace #5 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace Resort #27 - Beach View Suite

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$154

Tiny Home Camping Experience

St. Petersburg yurt

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$287

Tiny House Siesta - Yellow Lifeguard Stand Tiny House

Siesta Key hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$423

Tiny House - Green Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$465

Tiny House - Blue Lifeguard Stand

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$423

Tiny House - Margarita

Gulf Gate Branch house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$471

Tiny House - Flamingo

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$400

Tiny House - Seashell

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$315

Tiny House - The Siesta

Gulf Gate Branch house

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$374

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: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$114

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: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$458

Tropic Terrace Resort #59 - Beach View Penthouse

Treasure Island condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$258

Tropic Terrace #41 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$184

Tropic Terrace #15 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #44 - Beachfront Resort

Treasure Island condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$165

Tropic Terrace #37 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$154

Tropic Terrace #29 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$236

Tropic Terrace #49 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #55 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #35 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$154

Tropic Terrace #40 - Beachfront Resort

Treasure Island house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$208

Tropic Terrace #18 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #54 - Beachfront Resort

Treasure Island studio

  • Studio
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #48 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$117

Tropic Terrace #32 - Beachfront Resort

Treasure Island condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$166

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, Fridge

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: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$86

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: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$163

Private modern 3BR home, salt water pool

Bradenton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Wheelchair adapted, Fridge

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: Wheelchair adapted, Fridge

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: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$138

Sarasota Downtown, Best Location For Your Vacation !!!

Lido Key apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 7

Responds fast! avg. 1 hour 46 minutes

1 of 2 match: Wheelchair adapted, Fridge

1 of 2 filters match

Price per night from

$194

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, Fridge

1 of 2 filters match

Price per night from

$448

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, Fridge

1 of 2 filters match

Price per night from

$222

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rentals in Anna Maria Island

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