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Villas in Anna Maria Island and Holiday rentals - Holiday Lettings - Holiday Rentals Anna Maria Island

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3,045 Holiday homes

Bradenton Beach holiday home rental

Bradenton Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £277 / night

£1,778 / week

1 / 20

Holmes Beach holiday cottage let

Holmes Beach cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £370 / night

£2,309 / week

1 / 22

Holmes Beach holiday apartment rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Our all-time favorite vacation spot!!!” Easy rental process, great communication, excellent accommodations, condo is exactly as described!! We couldn't ask for anything more. Been back 4 times and counting since 2001. Love it!!

from £139 / night

£832 - £1,109 / week

1 / 28

Holmes Beach holiday home rental

Holmes Beach house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

from £555 / night

£3,879 / week

1 / 14

Apartment letting in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £210 / night

£1,552 / week

1 / 56

Holiday cottage in Bradenton Beach

Bradenton Beach cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

from £277 / night

£1,940 / week

1 / 25

Holiday cottage in Bradenton Beach

Bradenton Beach cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £301 / night

£2,771 / week

1 / 17

Apartment rental in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £210 / night

£1,552 / week

1 / 56

Holiday apartment rental

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £148 / night

£870 - £3,046 / week

1 / 62

Holmes Beach holiday apartment rental

Holmes Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £347 / night

£2,494 / week

1 / 30

Bradenton Beach holiday apartment rental

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £146 / night

£880 - £3,050 / week

1 / 47

Anna Maria holiday home rental

Anna Maria house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £336 / night

£2,347 / week

1 / 39

Condo rental in Holmes Beach

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

from £221 / night

£1,546 / week

1 / 31

Holiday villa in Bradenton Beach

Bradenton Beach villa

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from £462 / night

£3,233 / week

1 / 28

Apartment rental in Anna Maria Island with golf nearby

Anna Maria Island apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Perfect Condo and location” You will not be disappointed with this Condo. The place was clean, beds great, nice and cool from the wonderful heat of the day. 1 minute walk to an amazing beach and evening sunset. 2 minutes walk to a free trolly to take you from one end of the island to the other; and to a great grocery store. We will be returning, the only problem is...not soon enough! Do not hesitate to book this place. :-)

from £200 / night

£1,205 - £4,187 / week

1 / 70

Bradenton Beach holiday apartment accommodation

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £196 / night

£1,183 - £3,930 / week

1 / 49

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £159 / night

£1,109 / week

1 / 13

Holiday home in Bradenton Beach

Bradenton Beach house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 12

from £1,012 / night

£7,080 / week

1 / 44

Holiday home with swimming pool in Anna Maria

Anna Maria house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from £313 / night

£2,192 / week

1 / 42

Holiday townhouse in Bradenton Beach

Bradenton Beach townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £149 / night

£1,041 / week

1 / 13

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,320 - £4,572 / week

1 / 59

Holiday cottage in Bradenton Beach

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“Clean and modern in great location” Entire house recently renovated with modern appliances, central a/C, flat screen TV, dependable Wifi, unique design touches, cheery environment. Delightful owners very responsive. Young neighbors threw loud party while we were there. No idea if this is common. Twin beds designed more for children.

from £198 / night

£1,386 - £3,233 / week

1 / 39

Cottage rental in Bradenton Beach

Bradenton Beach cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

from £184 / night

£1,570 - £2,216 / week

1 / 25

Villa rental in Holmes Beach with shared pool

Holmes Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £169 / night

£1,183 / week

1 / 16

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £185 / night

£1,089 - £3,808 / week

1 / 60

Bradenton Beach holiday condo rental

Bradenton Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

from £221 / night

£1,546 / week

1 / 32

Holiday home with swimming pool in Holmes Beach

Holmes Beach house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

from £293 / night

£2,050 / week

1 / 49

Home rental in Holmes Beach

Holmes Beach house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,109 / night

£7,758 / week

1 / 20

Holiday home in Anna Maria

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,201 / night

£12,930 - £13,854 / week

1 / 53

Holiday condo in Anna Maria Island

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.

from £169 / night

£1,178 / week

1 / 68

Condo letting in Holmes Beach

Holmes Beach condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

from £194 / night

£1,340 - £1,386 / week

1 / 9

Holiday condo in Holmes Beach

Holmes Beach condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £277 / night

£1,940 / week

1 / 2

Holiday home with swimming pool in Anna Maria

Anna Maria house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

from £434 / night

£3,032 / week

1 / 65

Holiday home in Holmes Beach

Holmes Beach house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

from £151 / night

£1,054 / week

1 / 18

Holiday villa in Holmes Beach

Holmes Beach villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £159 / night

£1,112 / week

1 / 14

Holiday apartment with swimming pool, golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

from £172 / night

£989 - £3,431 / week

1 / 48

Holiday apartment with golf nearby in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

“Loved everything about our vacation” We had an amazing vacation. Everything in the condo was very clean and looked brand new. Bradenton beach is by far the best beach we have ever been to. There are plenty of great restaurants around and many fun day time activities to do as well. We hope to be back soon.

from £262 / night

£1,511 - £5,254 / week

1 / 48

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

from £229 / night

£1,320 - £4,572 / week

1 / 41

Home rental in Holmes Beach

Holmes Beach house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

from £1,663 / night

£11,545 - £12,930 / week

1 / 40

Holiday villa with shared pool in Holmes Beach

Holmes Beach villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from £128 / night

£893 / week

1 / 11

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Anna Maria Island holidays

Just south of Tampa Bay on the turquoise Gulf of Mexico, sits a quaint Barrier Island located on Florida's West Coast. Lined by a seven-mile strip of beautiful white-sand beaches, Anna Maria Island is a cosy paradise that has long been considered one of the state's hidden gems. Here, "Old Florida" charm abounds and visitors can get a feel for Florida, the way it used to be.

With seven miles of uninterrupted beach, Anna Maria Island offers plenty of opportunities to enjoy fun in the sun and explore. The island shares its beach life with local wildlife. Turtles visit from May - November every year (nest tours are offered in the summer) and year round visitors shouldn't be surprised to see manatees, dolphins, rays and exotic fish beyond the waves.

In addition to its picturesque beaches, Anna Maria Island is home to many award-winning dining options, including bistros, cafes and restaurants (there are no chain restaurants to be found). The island has been recognised nationally for its locally sourced food, unique menu items and on-the-water locations offering top views. Diners can expect gourmet dining options offering cuisine from England, France, Germany, Italy, Asia and Spain, as well as "Floribbean" dishes and seafood delicacies straight from the nearby sea. Top seafood choices include: grouper, red snapper, mullet and blue crab. Visitors are even invited to bring their catch into some of the area's top restaurants, like the Sandbar and Beachhouse.

For guests looking for fun off the sand as well, there are many art galleries, museums or aquariums in the area. And, the island is surrounded by nature parks and gorgeous naturally landscaped paths worth exploring.

Anna Maria Island also offers many top options for shopping at its many souvenir, jewellery, clothing and antique stores. Pine Avenue (known as the Greenest Little Main Street in America) is lined by great stylish boutiques and speciality shops and leads directly on to the 100 year old Anna Maria City Pier which offers picturesque views of the bay. Holmes Beach offers seven blocks of stores, small unique gift shops, adorable café's, art galleries and a grocery store. Additionally, stores on the newly restored Bridge Street in Bradenton Beach offers an unusual blend of arts and crafts unique to the island, reflecting its Bohemian roots.

Anna Maria Island also boasts a wide variety of accommodations ranging from historic bed and breakfasts, to beach-side cottages, cosy luxury homes, as well as condo rentals and spacious villas, which are all locally owned and operated and offer a unique experience. Tall sky-rise and commercial buildings do not exist on Anna Maria Island, with most accommodations measuring at less than three stories.

Additionally, the island is becoming a top choice for beach destination weddings. So much so that many are referring to the setting as the "Beach Wedding Capital of Florida". Forbes named Anna Maria Island the "#3 Prettiest City in the Country" in 2013 and was a "TripAdvisor Traveller's Choice Destination Winner 2013 and 2014" and #3 of the top 10 islands in the US to go to in 2014.

Information provided by: Bradenton Area Convention and Visitor's Bureau

Top Destination reviews

Gorgeous views,spectacular home!
Absolutely fantastic.

Just spent a week at this fantastic property. Party of 8 adults including family and friends from the UK. It was to celebrate a special birthday and we were not disappointed, the house exceeded our expectations and everyone loved it and of course the gorgeous views of the ocean were indeed a bonus. The kitchen was well stocked with everything you needed and we loved the pool area, we grilled several evenings and having the bar and large table everyone in the party could be seated. The bedrooms were very comfortable and so nicely decorated, large comfortable couches in the living room when you wanted to relax so it really was a wonderful experience. We will certainly be back.see more
Beautiful Anna Maria Island
FABULOUS!!

My husband and I went for our twenty-fifth wedding anniversary! Those were wonderful and amazing! Very communicative! Condo was absolutely perfect down to being well it equipped , a beautiful setting and furnished perfectly! We will definitely be going back again and again! … see more
Sea Waves in Anna Maria Island with Private Dock
A lovely holiday

We had a wonderful holiday on this very special Island, the location of the cottage is excellent and we very much enjoyed being able to watch the many beautiful birds from the deck. The Cottage is very convenient for all of the attractions of Anna Maria which is one of our favourite destinations, thank you Jenny, it was lovely to meet you and you were very helpful. Best wishes Christinesee more
A Pearl of a Beach Home - now with luxury Saltwater heated pool and hot tub
Great holiday

A lovely house, very well equipped. Good location for the beach. Really close to local amenities, easily within walking distance. Beautiful pool and spa. Spacious house, really enjoyed our table tennis tournaments in the garage. Great place … see more
Spectacular Beach House With GulfView Only Steps to a Pristine Beach
very comfortable, clean, fully-equipped and right by the beach

We stayed in May 2016 with 5 adults and had a very comfortable stay here. The house is exactly as per the photos and it's just a one minute walk to the beach. The best thing about the house was how equipped it was - especially for the beach - the trolley with the canopies, deck chairs etc made our beach days so easy. It was great having the bikes since there aren't many cafes or restuarants in the area (10min cycle away), and you definitely need a car for groceries etc. The owner is very friendly and helpful and checked several times that we were happy with everything. My only observation was that the there were many rentals available in that area during our stay and this one did seem relatively highly priced in comparison - perhaps because this area is more "upmarket", also the interior is nicer compared to some of the more dated places near by. All in all we had a great stay and Id recommend it to families and adults.see more

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