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Anna Maria Waterfront Vacation Rentals, Beach Rentals & More - 178 Rentals Available.

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178 Vacation rentals

Filters applied: Waterfront

(23)

1 / 49

Anna Maria House

  • 4
  • 8
  • 28 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0.2 mi
  • Swimming pool

Responds fast! Avg. 2 hours 37 minutes

“Whether you are a couple or three families under one roof, the layout of this home fits the bill. Three eating areas, three gathering areas plus the pool area is amazing. Newer homes on the island have five bedrooms....great...right but there is...”
- Review left on 06/25/2015

$201.00

Very Good (23 reviews)

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from $201.00 / night

(1)

1 / 21

Anna Maria House

  • 3
  • 6
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$573.00

Excellent (1 reviews)

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from $573.00 / night

1 / 51

Anna Maria Apartment

  • 5
  • 12
  • 4 nights min
  • Child friendly

$799.00

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from $799.00 / night

1 / 14

Anna Maria House

  • 2
  • 5
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$573.00

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from $573.00 / night

(2)

1 / 47

Anna Maria House

  • 2
  • 4
  • min stay varies
  • Swimming pool
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 9 minutes

$383.00

Excellent (2 reviews)

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from $383.00 / night

1 / 55

Anna Maria House

  • 4
  • 8
  • 4 nights min
  • Child friendly
  • Pet friendly

Responds fast! Avg. 1 hour 14 minutes

$687.00

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from $687.00 / night

Your search has been expanded 19.8 miles to include more rentals

(2)

1 / 27

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$152.00

Excellent (2 reviews)

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from $152.00 / night

(1)

1 / 66

Redington Beach House - 19.8 miles away

  • 5
  • 14
  • 3 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$343.00

Excellent (1 reviews)

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from $343.00 / night

1 / 13

Lakewood Ranch House - 18.9 miles away

  • 2
  • 4
  • 14 nights min
  • Swimming pool
  • Air conditioning
  • Private garden

$279.00

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from $279.00 / night

1 / 12

Bradenton Cottage - 16.9 miles away

  • 1
  • 4
  • min stay varies
  • Child friendly
  • Air conditioning

$107.00

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from $107.00 / night

1 / 16

Bradenton House - 10.2 miles away

  • 3
  • 4
  • min stay varies
  • Nearest beach 10 mi
  • Swimming pool
  • Child friendly

$155.00

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from $155.00 / night

1 / 8

Sarasota Condo - 12.6 miles away

  • 1
  • 2
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 9 mi
  • Swimming pool

$57.00

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from $57.00 / night

(18)

1 / 50

Treasure Island Condo - 15.5 miles away

  • 2
  • 5
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Car not necessary

Responds fast! Avg. 3 hours 1 minutes

“We absolutely loved our stay at sunset cove. The condo is very clean and has everything you could possibly need. Plenty of room for 2 adults and 2 teen girls. The location is great very close to restaurants and activities. We will definitely be...”
- Review left on 01/09/2017

$110.00

Excellent (18 reviews)

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from $110.00 / night

(2)

1 / 9

St. Petersburg Condo - 18.6 miles away

  • 1
  • 2
  • 30 nights min
  • Ask about children
  • Air conditioning
“I stayed for the month of May while finding a place for our move. Place is in great location with plenty to walk to. 10 minute walk and you are at great restaurants, movie theatre, and the bay. Place is great for a single person or a couple, and...”
- Review left on 06/01/2016

$37.00

Excellent (2 reviews)

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from $37.00 / night

(1)

1 / 33

Anna Maria Island Villa - 4.9 miles away

  • 2
  • 3
  • min stay varies
  • Child friendly

Responds fast! Avg. 3 hours 9 minutes

$201.00

Excellent (1 reviews)

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from $201.00 / night

(11)

1 / 13

Treasure Island Condo - 16.9 miles away

  • 1
  • 4
  • 2 nights min
  • Beach/lakeside relaxation
  • Ask about children
  • Air conditioning
“Wonderful property at the Malyn. Very personable owner, attentive to all our needs. Went above and beyond to help us out of a tight situation. The unit is designed in a delightful manner, views from our sliding door was gorgeous, sunsets to die for....”
- Review left on 07/25/2016

$167.00

Excellent (11 reviews)

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from $167.00 / night

(1)

1 / 23

Lido Key House - 17.8 miles away

  • 3
  • 9
  • 4 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$399.00

Excellent (1 reviews)

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from $399.00 / night

(1)

1 / 42

Treasure Island Condo - 15.5 miles away

  • 3
  • 8
  • 4 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning

$850.00

Excellent (1 reviews)

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from $850.00 / night

1 / 19

Madeira Beach Condo - 19 miles away

  • 2
  • 5
  • min stay varies
  • Swimming pool
  • Child friendly
  • Air conditioning

$258.00

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from $258.00 / night

(24)

1 / 30

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“Gulf front condo in Madeira Beach; location/view is outstanding and condo was fully equipped. Convenient to restaurants, shopping and attractions. Only two complaints were the carpet in unit was dirty, stained and worn and needed to be cleaned or...”
- Review left on 11/28/2016

$229.00

Very Good (24 reviews)

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from $229.00 / night

(3)

1 / 16

Bradenton House - 17.1 miles away

  • 3
  • 6
  • min stay varies
  • Nearest beach 20 mi
  • Swimming pool
  • Child friendly

Responds fast! Avg. 3 hours 50 minutes

“we rented this home for a week in July, the home is beautiful, it is equipped with every thing you could possibly need. the pool area was very relaxing and enjoyable. we loved the hone and would rent again...”
- Review left on 07/13/2014

$144.00

Excellent (3 reviews)

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from $144.00 / night

1 / 45

Anna Maria Island Condo - 2.5 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

Responds fast! Avg. 3 hours 29 minutes

$344.00

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from $344.00 / night

(22)

1 / 31

St. Pete Beach House - 12 miles away

  • 1
  • 4
  • 1 night min
  • Beach/lakeside relaxation
  • Nearest beach 1 mi
  • Child friendly

Responds fast! Avg. 2 hours 31 minutes

$167.00

Excellent (22 reviews)

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from $167.00 / night

(27)

1 / 11

Bradenton House - 17.2 miles away

  • 4
  • 10
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning
“The home was a great place for our group to stay. It was clean and well maintained. The location was ideal, close to golf courses and shopping and many good restaurants. We would definitely stay there again. The owner, Larry was very good to work...”
- Review left on 02/01/2017

$211.00

Excellent (27 reviews)

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from $211.00 / night

1 / 19

Holmes Beach Townhouse - 1.1 miles away

  • 3
  • 8
  • 4 nights min
  • Swimming pool
  • Ask about children
  • Air conditioning

$500.00

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from $500.00 / night

(21)

1 / 11

Holmes Beach Townhouse - 2.7 miles away

  • 2
  • 6
  • 7 nights min
  • Nearest beach 0.05 mi
  • Swimming pool
  • Child friendly
“This was my family's first visit to Anna Maria Island and it won't be our last. We loved the beaches, restaurants, and amazing sunsets. The Gulf View Townhouse was clean and centrally located, and it was an added bonus to have a pool on the...”
- Review left on 07/19/2016

$172.00

Very Good (21 reviews)

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from $172.00 / night

(1)

1 / 18

Madeira Beach Condo - 19 miles away

  • 2
  • 6
  • 7 nights min
  • Swimming pool
  • Child friendly
  • Air conditioning

$152.00

Excellent (1 reviews)

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from $152.00 / night

(9)

1 / 15

Madeira Beach Townhouse - 18.1 miles away

  • 2
  • 4
  • 7 nights min
  • Nearest beach 30 mi
  • Swimming pool
  • Child friendly
“I have stayed at Townhouse 343 for several years and have recommended it to several of my friends and co-workers. Neither I, nor any of my friends have ever been disappointed. The owners are hospitable and think of every detail to make your stay...”
- Review left on 10/08/2016

$118.00

Very Good (9 reviews)

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from $118.00 / night

(3)

1 / 38

Redington Beach Manor house - 19.7 miles away

  • 5
  • 12
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly
“This home was amazing. We brought three generations and had plenty of space--both for together times and when we wanted privacy! Three teenage girls enjoyed the privacy of the garage suite. We called it the bachelorette pad! The pool and patio area...”
- Review left on 10/22/2017

$1,145.00

Excellent (3 reviews)

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from $1,145.00 / night

1 / 17

Madeira Beach Condo - 18.3 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Pet friendly

Responds fast! Avg. 3 hours 30 minutes

$218.00

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from $218.00 / night

1 / 13

Anna Maria Island Apartment - 5 miles away

  • 2
  • 6
  • min stay varies
  • Child friendly
  • Air conditioning

$252.00

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from $252.00 / night

(3)

1 / 11

Sarasota Condo - 16.7 miles away

  • 2
  • 6
  • 30 nights min
  • Nearest beach 20 mi
  • Swimming pool
  • Ask about children
“This condo was extremely well appointed and had everything that we needed. We stayed 3 months and enjoyed every minute. The owners were gracious and responsive to every question. The view was outstanding. How much did we like it -we are renting it...”
- Review left on 03/30/2015

$115.00

Excellent (3 reviews)

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from $115.00 / night

(1)

1 / 13

St. Petersburg Apartment - 18.6 miles away

  • 1
  • 2
  • 30 nights min
  • Ask about children
  • Air conditioning
“great location,location,location comfortable has everything you need just bring yourself and your swim suit freindly safe neigborhood area all kinds of events at the bay two blocks away this is our third year staying here started with one month now...”
- Review left on 04/06/2016

$39.00

Excellent (1 reviews)

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from $39.00 / night

1 / 9

Lakewood Ranch Cottage - 19.2 miles away

  • 1
  • 2
  • 5 nights min
  • Nearest beach 10 mi
  • Air conditioning
  • Private garden

Responds fast! Avg. 3 hours 10 minutes

$126.00

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from $126.00 / night

1 / 21

Madeira Beach Condo - 19.1 miles away

  • 3
  • 8
  • 5 nights min
  • Beach/lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool

$264.00

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from $264.00 / night

(1)

1 / 13

St. Pete Beach Condo - 14.5 miles away

  • 2
  • 6
  • min stay varies
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$202.00

Very Good (1 reviews)

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from $202.00 / night

1 / 15

Madeira Beach Condo - 19.4 miles away

  • 2
  • 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Swimming pool
  • Child friendly

$287.00

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from $287.00 / night

(1)

1 / 38

St. Petersburg Apartment - 12.5 miles away

  • 2
  • 4
  • min stay varies
  • Beach/lakeside relaxation
  • Nearest beach 4 mi
  • Swimming pool

$82.00

Excellent (1 reviews)

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from $82.00 / night

1 / 34

St. Petersburg Condo - 12.3 miles away

  • 2
  • 4
  • min stay varies
  • Nearest beach 4 mi
  • Swimming pool
  • Child friendly

$85.00

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from $85.00 / night

1 / 16

Oneco Cottage - 11.4 miles away

  • 1
  • 2
  • min stay varies
  • Air conditioning
  • Pet friendly

$64.00

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from $64.00 / night