Holiday Houses in Anna Maria Island

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2,358 Holiday homes

runaway bay 2 bedroom condo with wonderful access to restaurant, beach, shopping

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

from £141 / night

£1,128 / week

Anna Maria Island, 2 Bed, 2 Bath Condo in quiet setting near to Beaches

Holmes Beach condo

2 bedrooms / 2 bathrooms / sleeps 4

10

from £91 / night

£635 - £841 / week

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

38

Responds fast! avg. 7 minutes

from £92 / night

£638 / week

2-Unit Beach to Bay Cottage...NOT Grandma's place!...100 feet to beach!

Bradenton Beach cottage

3 bedrooms / 2 bathrooms / sleeps 8

10

from £99 / night

£826 - £2,076 / week

AMI Bradenton Beach Ground Condo

Bradenton Beach condo

2 bedrooms / 1 bathroom / sleeps 4

1

from £118 / night

£708 / week

Beach side rental steps to Holmes Beach

Holmes Beach condo

1 bedroom / 1 bathroom / sleeps 6

from £77 / night

£540 / week

BAY FRONT HOUSE WITH PRIVATE DOCK

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 6

5

from £165 / night

£987 / week

Charming cottage w/ free WiFi just two blocks from the beach, near free trolley!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

from £152 / night

£1,059 / week

Dog-friendly cottage w/ private heated pool - minutes from beaches & more!

Anna Maria house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 56 minutes

from £269 / night

£1,881 / week

Canalfront home w/ pool, dock & lanai - 2 blocks to the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £212 / night

£1,480 / week

'Seascape' PEACEFUL, Newly renovated, steps to beach & fishing dock on bay

Bradenton Beach condo

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 2 hours 57 minutes

from £113 / night

£731 - £1,788 / week

BEACHFRONT HOME, PRIVATE BEACH, DOGS STAY FREE, GREAT VIEWS, WALKING BEACH

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 8

6

Responds fast! avg. 2 hours 23 minutes

from £188 / night

£1,315 / week

Islands End- 792 North Shore Dr, Anna Maria

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 6

from £71 / night

£493 - £780 / week

Cozy Cabana West - Private Pool - Close to Beach

Holmes Beach villa

2 bedrooms / 2 bathrooms / sleeps 6

6

Responds fast! avg. 2 hours 32 minutes

from £156 / night

£944 - £1,652 / week

AMI Island Living -Walk to Beach-Ground Level Unit

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

2

from £141 / night

£940 / week

CHARMING 2 Bed 2 Bath with Heated PRIVATE HEATED Pool SPA Sleeps 6 F

Holmes Beach townhouse

2 bedrooms / 2 bathrooms / sleeps 6

2

from £187 / night

£1,309 / week

A Puff Away East- 114 Magnolia Ave East, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £86 / night

£595 - £813 / week

Oceanfront dog-friendly home w/private pool & ocean view - right on the beach!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £541 / night

£3,782 / week

Bright and cheery waterfront home with private pool and spa

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £263 / night

£1,842 / week

Spacious house w/ private yard & great location near the beach - dogs ok!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £102 / night

£711 / week

Steps to Beach, Gulf View, Footprints in the Sand

Bradenton Beach apartment

2 bedrooms / 1 bathroom / sleeps 4

22

Responds fast! avg. 3 hours 21 minutes

from £149 / night

£850 - £1,038 / week

Sandy Toes- 116 Palmetto Ave, Anna Maria

Anna Maria house

2 bedrooms / 1 bathroom / sleeps 4

6

from £89 / night

£616 - £813 / week

Coconuts Tahitian 205

Holmes Beach apartment

1 bedroom / 2 bathrooms / sleeps 4

3

Responds fast! avg. 3 hours 25 minutes

from £123 / night

£679 / week

Palm Court Villas- 210 B Magnolia Ave, Anna Maria

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 4

1

from £123 / night

£677 - £944 / week

Watch Sunsets, Dolphins, or Just Relax - Bermuda Bay 1453

Bradenton Beach apartment

3 bedrooms / 3 bathrooms / sleeps 6

12

from £235 / night

£1,128 - £1,832 / week

742 Jacaranda Rd

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

from £175 / night

£1,222 - £2,626 / week

Ohana Hale Seaside 2 Bedroom

Anna Maria Island condo

2 bedrooms / 1 bathroom / sleeps 6

1

Responds fast! avg. 3 hours 16 minutes

from £127 / night

£799 - £1,269 / week

Blue Bayou

Holmes Beach apartment

2 bedrooms / 2 bathrooms / sleeps 6

9

from £118 / night

£679 - £1,085 / week

private pool/spa beach gear

Holmes Beach townhouse

4 bedrooms / 3 bathrooms / sleeps 8

1

from £423 / night

£2,960 / week

Ohana Hale North 2 Bedroom on Anna Maria

Holmes Beach house

2 bedrooms / 1 bathroom / sleeps 6

23

Responds fast! avg. 3 hours 16 minutes

from £128 / night

£802 - £1,274 / week

On the Beach Paradise d

Holmes Beach cottage

2 bedrooms / 1 bathroom / sleeps 6

6

Responds fast! avg. 2 hours 16 minutes

from £170 / night

£1,076 / week

Waterfront and dog-friendly home with private pool, dock, views, and lanai!

Anna Maria house

3 bedrooms / 3 bathrooms / sleeps 8

1

Responds fast! avg. 56 minutes

from £174 / night

£1,217 / week

Chateau Relaxo- 106 75th St, Holmes Beach

Holmes Beach house

3 bedrooms / 3 bathrooms / sleeps 6

from £112 / night

£780 - £1,026 / week

Old Florida-style cottage w/ private heated pool - walk to the beach - dogs OK!

Anna Maria house

2 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £136 / night

£947 / week

Coconuts Beach Front 106 Ground Floor

Holmes Beach apartment

1 bedroom / 1 bathroom / sleeps 4

6

Responds fast! avg. 3 hours 25 minutes

from £208 / night

£1,132 / week

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Bradenton Beach apartment

2 bedrooms / 2 bathrooms / sleeps 5

1

from £142 / night

£991 / week

'Elegance' 100 Steps from the Beach!

Bradenton Beach house

2 bedrooms / 2 bathrooms / sleeps 5

11

Responds fast! avg. 3 hours 48 minutes

from £245 / night

£1,710 / week

Beautiful, well-maintained home w/private pool - walk to beach, dining, & more!

Anna Maria house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 56 minutes

from £263 / night

£1,842 / week

1/2 price summer rate sale! 'HideAway Bay' Stunning bay view! Just remodeled!

Bradenton Beach bungalow

2 bedrooms / 1 bathroom / sleeps 5

1

Responds fast! avg. 2 hours 57 minutes

from £179 / night

£1,131 - £2,376 / week

Fun In The Sun- 304 Gulf Blvd, Anna Maria

Anna Maria house

4 bedrooms / 2 bathrooms / sleeps 8

1

from £200 / night

£1,395 - £2,216 / week

Viewing 40 of 2,358
rentals in Anna Maria Island

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