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

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1,745 Holiday homes

Holiday home in Bradenton Beach

Bradenton Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from £131 / night

£916 / week

1 / 36

Holiday apartment rental

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £224 / night

£1,396 - £1,935 / week

1 / 30

Holiday apartment in Holmes Beach

Holmes Beach apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £213 / night

£1,486 - £1,921 / week

1 / 32

Holiday home in Holmes Beach

Holmes Beach house

3 bedrooms • 2 bathrooms • sleeps 6

from £281 / night

£1,963 - £2,310 / week

1 / 38

Bradenton Beach holiday condo rental

Bradenton Beach condo

2 bedrooms • 2 bathrooms • sleeps 6

from £214 / night

£1,499 / week

1 / 18

Home rental in Holmes Beach

Holmes Beach house

3 bedrooms • 2 bathrooms • sleeps 6

from £295 / night

£1,643 - £2,348 / week

1 / 37

Holiday apartment with golf nearby in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £118 / night

£824 - £1,121 / week

1 / 36

Holiday townhouse in Bradenton Beach

Bradenton Beach townhouse

3 bedrooms • 3 bathrooms • sleeps 6

from £209 / night

£1,457 / week

1 / 16

Holiday apartment in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £223 / night

£1,389 - £1,926 / week

1 / 22

Holiday apartment in Holmes Beach

Holmes Beach apartment

3 bedrooms • 2 bathrooms • sleeps 6

from £213 / night

£1,486 - £1,921 / week

1 / 33

Holiday home in Holmes Beach

Holmes Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from £232 / night

£1,624 - £1,972 / week

1 / 24

Holmes Beach holiday apartment rental

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £178 / night

£1,103 - £1,602 / week

1 / 31

Holiday apartment with shared pool in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £231 / night

£1,616 - £2,017 / week

1 / 26

Holiday apartment in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £232 / night

£1,624 - £2,027 / week

1 / 28

Holiday apartment with golf nearby in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £176 / night

£1,086 - £1,336 / week

1 / 36

Holiday apartment rental

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 6

from £178 / night

£1,103 - £1,602 / week

1 / 28

Holiday apartment in Holmes Beach

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 4

from £195 / night

£1,361 - £1,898 / week

1 / 29

Holmes Beach holiday apartment rental

Holmes Beach apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £176 / night

£1,086 - £1,336 / week

1 / 36

Holiday condo in Holmes Beach

Holmes Beach condo

2 bedrooms • 2 bathrooms • sleeps 4

from £97 / night

£678 - £967 / week

1 / 31

Holiday condo rental

Holmes Beach condo

1 bedroom • 1 bathroom • sleeps 6

from £58 / night

£403 / week

1 / 40

Holiday villa in Holmes Beach

Holmes Beach villa

2 bedrooms • 2 bathrooms • sleeps 6

from £151 / night

£1,004 - £1,582 / week

1 / 22

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 £87 / night

£750 - £3,334 / week

1 / 39

Bradenton Beach holiday condo rental

Bradenton Beach condo

1 bedroom • 1 bathroom • sleeps 2

from £216 / night

£1,412 - £1,807 / week

1 / 35

Bradenton Beach holiday home rental

Bradenton Beach house

2 bedrooms • 2 bathrooms • sleeps 4

from £211 / night

£1,179 / week

1 / 20

Holiday home in Anna Maria

Anna Maria house

3 bedrooms • 2 bathrooms • sleeps 8

from £166 / night

£1,160 / week

1 / 44

Holiday home rental

Holmes Beach house

2 bedrooms • 1 bathroom • sleeps 6

“Wonderful place, wonderful people” Danny Chin did a beautiful job of remodeling this duplex. It was lovely and comfortable. Danny and Brenda were very kind and gracious hosts. They took care of our every need, and answered our every question. The home was spotless when we moved in. Plenty of room for a couple. The bedroom had a nice ceiling fan above the bed. The bed was comfortable, with a large walk-in closet. All kitchen appliances worked well. The kitchen was well stocked with everything we needed. The air-conditioning worked flawlessly. The location was great. A very short walk to the beach and shopping. My wife and I would gladly stay there again.

from £150 / night

£916 - £1,250 / week

1 / 17

Anna Maria Island holiday condo rental

Anna Maria Island condo

2 bedrooms • 1 bathroom • sleeps 6

from £150 / night

£1,250 / week

1 / 23

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

3 bedrooms • 3 bathrooms • sleeps 6

from £209 / night

£1,458 - £1,999 / week

1 / 27

Holiday home in Bradenton Beach

Bradenton Beach house

2 bedrooms • 1 bathroom • sleeps 6

“Perfect! Clean, convenient!” We loved staying here! I is not only clean, but up to date and convenient to the beach. We walked every day. I loved sitting on the porch watching birds. The free trolley means your park your car and truly enjoy your stay. We have reservations to stay again!!

from £150 / night

£916 - £1,250 / week

1 / 24

Holiday home in Anna Maria

Anna Maria house

3 bedrooms • 3 bathrooms • sleeps 8

from £262 / night

£1,832 - £5,621 / week

1 / 37

Cottage rental in Holmes Beach

Holmes Beach cottage

2 bedrooms • 1 bathroom • sleeps 6

from £151 / night

£951 / week

1 / 13

Holiday townhouse in Bradenton Beach

Bradenton Beach townhouse

2 bedrooms • 2 bathrooms • sleeps 5

from £86 / night

£601 / week

1 / 45

Holiday home rental

Bradenton Beach house

3 bedrooms • 3 bathrooms • sleeps 6

“Excellent condo with elevator for all the ladies” Sharkey's Bar and Grill was by far the bet prime rib around. Sandbar had the best fish platter and Skinny's the best burgers and the City Pier Restaurant had great shrimp overall excellent food all around.

from £271 / night

£1,836 / week

1 / 26

Cottage rental in Bradenton Beach

Bradenton Beach cottage

4 bedrooms • 4 bathrooms • sleeps 15

from £108 / night

£750 - £5,001 / week

1 / 57

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

2 bedrooms • 2 bathrooms • sleeps 5

from £126 / night

£876 / week

1 / 13

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 £126 / night

£876 / week

1 / 30

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 £90 / night

£625 - £941 / week

1 / 28

Holiday home in Anna Maria

Anna Maria house

3 bedrooms • 2 bathrooms • sleeps 6

from £324 / night

£2,268 / week

1 / 23

Holiday home in Anna Maria

Anna Maria house

3 bedrooms • 3 bathrooms • sleeps 6

from £222 / night

£1,551 / week

1 / 29

Holiday apartment in Bradenton Beach

Bradenton Beach apartment

2 bedrooms • 1 bathroom • sleeps 6

from £150 / night

£1,250 / week

1 / 14

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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
Brand New Renovation Sea Waves Cottage
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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