Vacation Rentals & Beach Rentals in Anna Maria Island

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142 beach rentals

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

“Amazing Oceanview Pool Home and Perfect Location On Anna Maria Island” Let me first say that Mark (the home owner) exceeded any and all expectations for our 15th wedding Anniversary! We booked last minute and when we wanted to stay an additional day Mark rescheduled planned maintenance in order to accommodate us. When we arrived there were fresh flowers, wine, cookies, music and a Anniversary Cake for us! The Beautiful ocean view pool home is in a perfect location on Anna Maria Island and equipped with everything you will need: floats for the pool, anything you would need to take to beach across the street, bikes to explore the island, a large kitchen stocked with everything you need to cook, very comfortable beds and spacious rooms, fresh orchids throughout the home, library of DVD's and books, and I could just keep going...make sure you take the bikes and explore - go to the Museum, to bean point, have fresh grouper sandwich at the Rod and Reel Pier, ride down to Two Scoops for an ice cream and take a walk on the City Pier, on Fridays at 12:30 you can pick up amazing fresh bread at Olive Oil Outpost with some other goodies, go have a custom snack at the Donut Experiment, A drink at the Sandbar Rest., Lunch or Dinner at the Waterfront is amazing, and more all a short bike ride away. All my wife and I can say is what a wonderful week and we will be back for sure!

Responds fast! avg. 7 minutes

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Price per night from

$397

Steps to Beach, Gulf View, Footprints in the Sand

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

“Footprints in the sand” We had a great time on Anna Maria Island. Footprints in the sand,its closeness to the beaches,restaurants and shops made it very convenient.The place was well stocked with all basic needs & amenities that were listed. Thanks (Note) 1. We were a little annoyed at times from the noise that came from upstairs tenant when their child would run and jump and bang their toys or something on the floor. 2. Bed sheet was clean but stained 3. Toilet leaks sometimes near base We thank you for the use of your place and I'm sure you will find things in good order. Thanks Carlos & Maria Diaz

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$147

On the Beach Paradise d

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

“Absolutely beautiful!” Everything was perfect. Enjoyed coffee on the beach every morning and beautiful sunsets every evening. Can't wait to go back next year!

Responds fast! avg. 2 hours 19 minutes

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$206

'Elegance' 100 Steps from the Beach!

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 5

“Amazing!” This house has it all and a perfect location makes it an even more wonderful place to vacation. We hope to be back soon!

Responds fast! avg. 3 hours 49 minutes

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Price per night from

$297

The Lime Door

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

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$278

Beautiful luxury beach front condominium

Anna Maria condo

3 bedrooms / 4 bathrooms / sleeps 6

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$722

5 Star - Private Pool & Dock, and Steps Away from the Beach - Fall Availability

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 24 minutes

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Price per night from

$399

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.

Responds fast! avg. 1 hour 8 minutes

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Price per night from

$131

Update One Bedroom/One Bath with view and steps to beach unit 234 runaway bay

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

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Price per night from

$110

Charming 2 Bedroom/2 Bath Cottage on a Canal

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

Responds fast! avg. 3 hours 39 minutes

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$308

Ah this is it v2.0! Lemon Cottage w Pool!! Relax!!

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 6

“Way more than we expected!” Our week at Lemon Cottage was just excellent! Owner, Chris, has thought of everything we would need for the beach. The house is lovely inside, and landscaped just as nicely outside. We used the two bikes to explore, and we took many walks. The lanai area, with pool, is so inviting, that we managed to spend many hours out there just relaxing and trying to decide why we needed to move on to any activity at all! One of the things we did was to take a boat trip with Captain Kim (which I had done before). We stopped at the low places in the bay at low tide and held many live sea creatures...a great trip for adults as well as children. Mote acquarium is also high on my list, and they also have an educational boat tour of Sarasota Bay. Ringling mansion tour and grounds was lovely as well, even though we were caught in a deluge of rain. Lemon Cottage was indeed a lovely place to spend a week and we are hopeful that we will be able to stay there again. I highly recommend it!

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$200

Holmes Beach Family Home w/Private Pool & 3 Decks!

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

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$295

Anna Maria Island Private Tropical Garden Home

Holmes Beach house

3 bedrooms / 2 bathrooms / sleeps 6

“Best rental, best hosts -- hands down!” I booked this rental with the intention of relaxing on the beach, soaking up the sun and hanging out with family for just over a week. Hurricane Irma had other plans, and we had to cut our vacation short. But I cannot overemphasize how gracious Kent and Pa were as hosts. Because of them--and because of how great their property is--we had such a great time before we had to evacuate. And Kent went above and beyond to make sure we had the most up-to-date weather forecasts, so that instead of watching sometimes sensationalized TV reporting we could maximize our shortened vacation with peace of mind and still safely make it off the island and eventually out of Florida with my disabled father and baby daughter. Even after the evacuation, Kent and Pa continued to check up on us and processed a refund without hesitation for the days we were evacuated. Those particular circumstances hopefully will never be applicable to anyone else, so let me say a few things about the property itself. It is AWESOME! The pool area is the best I've ever experienced, and the house is so spacious you never feel on top of one another. It's also walking distance from just about everything you could want on AMI (with immediate vicinity to the trolley stop), but landscaped so beautifully that you feel like you're on your own private island. I echo other reviews that there is a temptation not to rave about it, because you really want it all to yourself. I mean, where else could you actually deal with fleeing from a hurricane and still want to go back the first chance you get?! We can't wait to return to this little slice of paradise. We'd been to Anna Maria Island before at a bed and breakfast, and had a great time then too, but nothing can beat this rental. Wishing Kent and Pa all the best with the cleanup and repairs in the wake of Irma. I have no doubt they will restore it to the same pristine condition it existed when I checked in, because it is so obvious how much they truly care for this fantastic property.

Responds fast! avg. 3 hours 10 minutes

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$294

Chic~ Pet Friendly~ Brand New Heated Pool/Spa

Holmes Beach house

2 bedrooms / 3 bathrooms / sleeps 4

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$263

5 Bed/3.5 Bath/2900sq ft/Heated Pool/Golf Cart/Game Room/Beach Across St

Bradenton Beach house

5 bedrooms / 4 bathrooms / sleeps 14

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Price per night from

$1,370

On the Beach Paradise u

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 2 hours 19 minutes

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Price per night from

$207

Contemporary Beach House, Very Private Yard & Pool - 1.5 Blocks to Beach

Holmes Beach house

2 bedrooms / 2 bathrooms / sleeps 5

Responds fast! avg. 1 hour 50 minutes

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$196

NEW! Waterfront Holmes Beach Condo w/ Pool Access!

Holmes Beach condo

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 4 minutes

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Price per night from

$101

Treehouse Escape

Bradenton Beach house

6 bedrooms / 5 bathrooms / sleeps 18

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Price per night from

$1,029

The Magnolia Lady - Anna Maria Beach Front Rental

Anna Maria house

4 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$630

Beautiful Sunkst Cottage Bradenton Beach - AMI-Tropical Setting - Heated Pool

Bradenton Beach house

3 bedrooms / 2 bathrooms / sleeps 10

“Rain” The house was adorable. It was well stocked considering we couldn't go out due to the rain. It is close to the beach,just a short walk.

Responds fast! avg. 3 hours 46 minutes

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Price per night from

$302

Surfside AMI, Many Amenities included!

Holmes Beach house

5 bedrooms / 4 bathrooms / sleeps 10

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Price per night from

$899

Anna Maria Island Beach Paradise

Anna Maria Island condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$458

Songbird Cottage

Anna Maria Island cottage

2 bedrooms / 1 bathroom / sleeps 5

Responds fast! avg. 1 hour 30 minutes

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Price per night from

$110

Anna Maria Island Beach Breeze

Anna Maria Island condo

2 bedrooms / 1 bathroom / sleeps 6

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$343

The Anna Maria Island Beach Paradise 10

Anna Maria Island condo

1 bedroom / 1 bathroom / sleeps 3

Responds fast! avg. 3 hours 48 minutes

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Price per night from

$164

SAPPHIRE - HARBOR ISLE

Bradenton Beach townhouse

3 bedrooms / 3 bathrooms / sleeps 6

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Price per night from

$286

Great rentals within 20 miles that match your search

Siesta Key Oceanfront on Gulf with western sunsets, 1250 sq ft Townhome

Siesta Key villa

2 bedrooms / 3 bathrooms / sleeps 4

“Absolutely Perfect---one Kodak sunset after another” This townhome was gorgeous! We totally enjoyed our 3 week stay and hated to leave. Kelley (owner) could have not been more helpful. We fished off the dock and enjoyed watching the birds fish then dry their wings. Town is a short, enjoyable jaunt. Just a few blocks further are the most gorgeous beaches with sand like flour! If you are adventureous, walk to Point of Rocks at beach access 13 for the best shelling ever (only at very low tide)!!! We would come back in a heartbeat. The views from the lanai and upstairs balcony were awesome. Townhome was beautifully maintained and fully stocked. Thanks to Kelley and her daughter for a never-to-be-forgotten vacation.

Responds fast! avg. 2 hours 13 minutes

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Price per night from

$138

E12-Pass a Grille Isl Steps to Beach w/WiFi&Bikes

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 2

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Price per night from

$138

Late SALE Sep/Oct only -Lakeside villa Uni. Park,golf,cycles,pool, beach

Sarasota villa

3 bedrooms / 2 bathrooms / sleeps 4

“A perfect setting and location” Everything about this vacation is perfect from start to finish. Joyce guides you through the pre vacation procedure seamlessly. All relevant information is sent concerning local amenities and events occurring during your stay. The house is spacious, clean and full of all the homely touches to make your stay so enjoyable. You can have a chilled out holiday round the pool and barbecue, or for the more energetic like us, there is golf and tennis on the doorstep. You can swim in the pool at the house or there is a 15 metre community pool round the corner. The beaches are a short drive from the villa, fantastic white sands with plenty of space for the sun seekers. There are plenty of good restaurants in the locality if you choose to eat out, and shopping malls are nearby for those gifts to take back home. All in all a fantastic vacation and excellent value. My wife and I have now returned 3 times from the U.K. Enough said !!!!

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$205

The MacGregor House is 1925 Old Florida elegance

Sarasota house

4 bedrooms / 3 bathrooms / sleeps 7

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Price per night from

$314

Florida Ocean Front Condo March 21- March 28 or April 11 -21, 2020

Longboat Key condo

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 41 minutes

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$331

Charming 2 Bedroom House, Fenced and Private

Sarasota house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 2 hours 21 minutes

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Price per night from

$229

Modern Waterfront St Pete Beach Private Pool Home

St. Pete Beach house

3 bedrooms / 2 bathrooms / sleeps 8

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Price per night from

$221

Serene Sarasota Getaway near shopping and golfing.

Fruitville villa

3 bedrooms / 2 bathrooms / sleeps 6

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Price per night from

$115

NW Bradenton Exectitive Home

Bradenton house

4 bedrooms / 3 bathrooms / sleeps 10

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Price per night from

$451

NEW - Desirable Art District

Gulfport bungalow

2 bedrooms / 1 bathroom / sleeps 6

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Price per night from

$109

(N22)Island Beach House 2ndfloor w/ Wifi & Bikes

St. Pete Beach cottage

1 bedroom / 1 bathroom / sleeps 4

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Price per night from

$185

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