Vacation Rentals & Beach Rentals in Anna Maria Island

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419 beach rentals

Luxury 3BR GulfFront "Grateful to be at the Gulf"

Hudson apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Responds fast! avg. 1 hour 59 minutes

Match: Climbing frame Pets

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Price per night from

$99

Savannah

Davenport villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Excellent as usually” We just got back again and the house was excellent as usually no complaints at all y'all will definitely enjoy it.

Responds fast! avg. 2 hours 34 minutes

Match: Climbing frame Pets

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Price per night from

$126

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Charming 3Bd Close to Disney * 3109 Sun Lake

Four Corners apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Pets

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Price per night from

$139

First Floor Beachfront Apartment

Cocoa Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 of 2 match: Climbing frame, Pets

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Price per night from

$126

Updated Condo in Beachfront Complex

Cocoa Beach apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 of 2 match: Climbing frame, Pets

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Price per night from

$103

Beachfront Condo - Best Price, Panoramic View

Cocoa Beach apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Awesome rental!!!” My husband and I rented this place right on the beach for a week and we couldn't have asked for anything more (except maybe better weather, haha)!! Clean, wonderful, homelike accommodations! Can't wait to use this rental again! Suzan

1 of 2 match: Climbing frame, Pets

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Price per night from

$126

BAYSIDE CONDO WITH BOAT

Key Largo apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Want to go back” We just got home from our vacation in this apartment. We loved it. Jay took great care of us and was quick to help with any problems or needs. We rented the boat with the apartment and loved being able to walk downstairs and get onto our boat and out fishing for the day. We enjoyed using the grill on the porch and being able to eat our dinner outside enjoying the weather and views. We will definately return again. Thanks for a great vacation Jay.

1 of 2 match: Climbing frame, Pets

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Price per night from

$430

3 BR 3 BA Oasis, perfect location in Olde Naples

Naples house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

“Lovely location in Naples” Our family of five (three boys under the age of 11) spent a wonderful week in this home. We found everything to be just as described and very comfortable. The house is clean and very well stocked with everything you need to enjoy the sun and live comfortably. The pool is delightful, the neighborhood is quiet & inviting, and the beach/restaurants/bars/shops are just a short walk/bike ride away. We even found an ice cream shop with several vegan gelato flavors that our egg/dairy/nut allergic son could enjoy. We grilled out most evenings so that the boys could enjoy the pool and the parents could relax on the porch with a cocktail. The owners could not have been more responsive, accommodating, and hospitable. It was a truly delightful experience!

1 of 2 match: Climbing frame, Pets

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Price per night from

$500

“It does not get any better than this in Cocoa Beach” There is check-box beneath this text field asking if I'd recommend this vacation rental to a friend. Absolutely not. No way. I'm not telling anybody, I'm keeping this place to myself. We were in town for the annual Cocoa Beach Art Show, plus a class reunion. Rooms were tight in CB, and many of our friends were staying at the local chain hotel/motels. I had first heard about Jackie and Dave's guest cottages a few months ago, but I didn't act. Much to my surprise, it popped up on TA and was available for the weekend. Best move we ever made. The Manatee Suite is over-the-top great. Bordering on kitsch, but not. Beach Kitsch. Brightly painted stucco, manatees, mermaids, sea turtles, and oh that beautiful spacious lanai, about as big as the entire suite. And a koi pond. All enclosed in a very private tropical garden that gives one little incentive to ever leave. There is a very comfy queen bed...a king would be nice, but would seriously cut into the navigation...and a kitchenette/hang-out area with a pull-out perfect for a couple of little ones or just to flop and watch tv (wall mounted flat-screen, extends to full view in either of the two rooms). No stove in the kitchenette, but a fridge and micro, as well as coffee maker and all the basic utensils and plates and drinkware. The Manatee Suite is in the back of the cottage, with the owner's residence and another suite out front. This is perfect, as it provides a buffer from the traffic noise of A1A. Jackie and Dave's little doggie will great you every time you walk by. The gate locks, adding another level of privacy to the beautiful lanai on a sunny day. ;) My wife and I grew up in Cocoa Beach, and return regularly. For some odd reason we'd never heard of the Done Roam Inn Guest Cottages. I hesitate to tell anyone else about it, because it is simply the best place in CB for for a casual vacation. Located one in from the corner of 3d St. North and AIA, it's within walking distance of virtually everything Downtown Cocoa Beach has to offer in terms of restaurants (breakfast, lunch, dinner), bars, coffee shops, you name it. We parked the car and rarely used it. Of course, the beach is right across the street. I mean, like right there. The cottage also comes with a couple beach chairs and extra beach towels. It felt like we were staying with some friends, certainly not in a cold hotel. I think our future plans will be to rent both suites and have a Thanksgiving on the beach. This is a homey and comfy as you'll find in Cocoa Beach...take it from a guy who grew up here and knows his way around this town. My only advice would be to NOT stay here at any of the times we're in town. I'll be sad if the Manatee Suite is not available for us. We showed a few pictures and invited a few friends over and got the same response from every one...jaw dropping, "why didn't we stay here?!" I may be shooting myself in the foot by posting this review, but Jackie and Dave deserve all the positive vibes I can send. In my travels I've found few places that have made me feel so welcome, so at home, than Done Roam Inn. When we checked out, Jackie and my wife shared a hug. I cannot think of one negative thing to post about the place.

Responds fast! avg. 3 hours 52 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$201

Disney for the Holidays! 3 Bedroom in Orlando

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Pets

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Price per night from

$315

Orlando Florida, 3-Bedroom Lock-off Disney!

Orlando apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Pets

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Price per night from

$344

Waterside

Kissimmee house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$287

Budget Friendly Spacious Home With Private Pool Area 6 Miles To Disney

Kissimmee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

Villa Paradiso

Kissimmee villa

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$287

Room For Everyone! Spacious Private Pool & Spa Home.

Kissimmee house

  • 6 bedrooms
  • 4 bathrooms
  • sleeps 10

“Thanksgiving 2016” Great home, clean and spacious. The Gemstone company was very accommodating and Mary, the host, was available even during the holiday. Definitely recommend this home for trips with large groups.

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$287

Golf Oasis Anyone? Stay Right Next to Champions Gate!

Davenport house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“Vacation Home in Davenport, FL” Great experience in this home, booking was very easy and communication with owners very agile. House was as described in the advertising and is a very comfortable home for family and/or groups up to 8 people.

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

Located Only 6 Miles To Disney Property In Gated Community

Kissimmee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

“A dream week” A beautiful home..spacious..confortable.. quiet and safe.. close to attractions..

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

Watch Disney Fireworks From The Privacy of Your Pool

Davenport studio

  • Studio
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

So Close To It All With A Country Feel

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Great place to stay with kids, for the kids and adults!” Really nicely acquitted, close to everything. Great stay but the only thing that could have been better was if we didn't have to go off site and try to figure out where the place to get registered for our stay was. Otherwise I would definitely and will definitely be back again.

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

Watch Fireworks Over the Water Minutes From Disney

Kissimmee house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Watersedge of Indian Wells” This was a lovely house and it made our stay perfect. It was clean and well equipped. The rooms bedrooms were large as well as the beds. The kitchen well set-up and the living-room furniture very comfortable. The pool area was very lovely and the view over the pond was beautiful. The only real drawback of the pool is the safety alarm on the door to access it. The alarm rings every time you open this door and it becomes a fairly minor annoyance. The managers of this house were always quick to respond to queries and every staff member I spoke to was very friendly and polite. Check-in and check-out procedures were similarly simple. The house was in a great location only 15 minutes drive to Disney and 20 minutes to Universal. Walmart is also located just 5 minutes walk away. A great place that I gladly recommend it!

Responds fast! avg. 1 hour 9 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$172

Palm Retreat- FOR OWNER USE ONLY

Davenport apartment

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

“Amazing” One of the best time ever!! Thank you and we would stay there again.

1 of 2 match: Climbing frame, Pets

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Price per night from

$117

CCVR - Villa Paloma

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Pets

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Price per night from

$223

CCVR - Villa Leonie

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Pets

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Price per night from

$300

CCVR - Villa Saxony

Cape Coral house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 of 2 match: Climbing frame, Pets

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Price per night from

$283

CCVR - Villa Moody River

North Fort Myers house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Pets

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Price per night from

$169

CCVR - Villa Country Club Residence

Biggar house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 of 2 match: Climbing frame, Pets

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Price per night from

$277

Vista Dreams

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$171

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$247

Gentle Breeze

Orlando house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$171

Serene Waters

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$195

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$247

Tropical Essence

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$178

Waterside at Vista Cay

Orlando condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$179

Lakeside Luxury

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$194

Contempo Suite

Orlando condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$166

Lakeview Penthouse

Orlando condo

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$224

Kings Palace

Orlando house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$217

Elegant Luxury

Orlando house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 53 minutes

1 of 2 match: Climbing frame, Pets

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Price per night from

$148

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rentals in Anna Maria Island

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