Vacation Rentals with Pool in Anna Maria Island

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Filtering by: Swimming pool

1,803 vacation rentals

(46) Excellent 

21

Gulf Beach Place - Just a few steps from the beach

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Another Fantastic Stay” This is my second time staying at Kay’s Gulf Place Condo! Very clean, comfortable and charming! Location has it all! Sunsets from the rooftop deck are to die for! No detail missed!
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Price per night from

$121

Responds fast!
avg. 1 hour 56 minutes

Price per night from

$121

(9) Very Good 

29

The beautiful Cove on Anna Maria Island

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0.8 mi
  • Swimming pool
“Beautiful condo, close to everything!” Everything was perfect in the condo which was new and updated! The 2 new full size beds in the 2nd bedroom were too hard. The pool was a nice size and stayed sunny most of the day. Shopping was close and the c
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Price per night from

$105

Price per night from

$105

18

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

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 30 nights min

  • 2 bedrooms
  • sleeps 6
  • 30 nights min
  • Nearest beach 1 mi
  • Swimming pool
  • Car not necessary

Price per night from

$173

Price per night from

$173

(38) Excellent 

123

Ocean View 3 bedroom, pool, North Shore Drive

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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 M
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Price per night from

$207

Responds fast!
avg. 49 minutes

Price per night from

$207

25

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

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$237

Price per night from

$237

(3) Excellent 

22

Cozy Cabana West - Private Pool - Close to Beach

Anna Maria Island / Holmes Beach

Holmes Beach villa

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$187

Responds fast!
avg. 3 hours 53 minutes

Price per night from

$187

41

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

Anna Maria Island / Anna Maria

Anna Maria house

4 8 min stay varies

  • 4 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$358

Price per night from

$358

52

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

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$537

Price per night from

$537

37

Bright and cheery waterfront home with private pool and spa

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$303

Price per night from

$303

48

Midnightchannel

Florida / Anna Maria Island

Anna Maria Island house

7 16 7 nights min

  • 7 bedrooms
  • sleeps 16
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$458

Price per night from

$458

43

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

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$304

Price per night from

$304

(1) Excellent 

14

AMI Bradenton Beach Ground Condo

Anna Maria Island / Bradenton Beach

Bradenton Beach condo

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Air conditioning

Price per night from

$173

Price per night from

$173

(31) Excellent 

Certificate of Excellence

52

Happy Island Cottage with heated private Pool

Anna Maria Island / Holmes Beach

Holmes Beach house

3 8 6 nights min

  • 3 bedrooms
  • sleeps 8
  • 6 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Exceeded expectations!” For several years, I've wanted to spend Christmas on AMI with my family. This past Christmas, I was able to do that, and we stayed at Happy Island Cottage. This was a wonderful house to stay in, and Alex was great and very re
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Certificate of Excellence

Price per night from

$309

Responds fast!
avg. 2 hours 13 minutes

Price per night from

$309

(11) Excellent 

25

'Elegance' 100 Steps from the Beach!

Anna Maria Island / Bradenton Beach

Bradenton Beach house

2 5 4 nights min

  • 2 bedrooms
  • sleeps 5
  • 4 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“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!
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Price per night from

$298

Responds fast!
avg. 1 hour 43 minutes

Price per night from

$298

(7) Very Good 

23

**PARADISE RETREAT IN BRADEN RIVER LAKES**

Anna Maria Island / Bradenton Beach

Bradenton Beach house

3 10 min stay varies

  • 3 bedrooms
  • sleeps 10
  • min stay varies
  • Beach / lakeside relaxation
  • Nearest beach 6 mi
  • Swimming pool
“Just like being at home.” Great location very quiet neighborhood, Close to grocery, gas, restaurants. We were 30 minutes to an hour from different beaches, we visited 3, Clearwater, Anna Marie Island and Siesta Key. Then we could come back to relax in
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Price per night from

$127

Responds fast!
avg. 1 hour 30 minutes

Price per night from

$127

28

Bermuda Bay 1467

Anna Maria Island / Bradenton Beach

Bradenton Beach condo

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly

Price per night from

$172

Responds fast!
avg. 1 hour 2 minutes

Price per night from

$172

(12) Excellent 

Certificate of Excellence

27

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

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

3 7 7 nights min

  • 3 bedrooms
  • sleeps 7
  • 7 nights min
  • Beach / lakeside relaxation
  • Nearest beach 0 mi
  • Swimming pool
“Great place, great location, and everything you need!” We stayed here to go to my sister's wedding at The Beach House. We loved this townhouse. It had spacious rooms, beautiful decor, and a great view of the ocean from the balcony. I was really imp
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Certificate of Excellence

Price per night from

$196

Price per night from

$196

35

NEW LISTING! Breezy condo w/shared pool -minutes from beach & dining

Anna Maria Island / Bradenton Beach

Bradenton Beach house

1 4 min stay varies

  • 1 bedroom
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$107

Price per night from

$107

(2) Very Good 

15

AMI Island Living -Walk to Beach-Ground Level Unit

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 4 7 nights min

  • 2 bedrooms
  • sleeps 4
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Suitable for children age 5+

Price per night from

$173

Price per night from

$173

23

Dog-friendly house with private pool, island views & nearby beach access!

Anna Maria Island / Anna Maria

Anna Maria house

2 4 min stay varies

  • 2 bedrooms
  • sleeps 4
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$212

Price per night from

$212

(2) Excellent 

39

Dolphin Pointe

Anna Maria Island / Anna Maria

Anna Maria house

3 8 7 nights min

  • 3 bedrooms
  • sleeps 8
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$278

Responds fast!
avg. 1 hour 9 minutes

Price per night from

$278

(33) Very Good 

Certificate of Excellence

46

Gorgeous views,spectacular home!

Anna Maria Island / Anna Maria

Anna Maria house

5 12 min stay varies

  • 5 bedrooms
  • sleeps 12
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Majestic Views” Our family loved our visit to Anna Maria. The house is gorgeous and spacious. My kids enjoyed the pool and eating outside. We hope to return in the near future.
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Certificate of Excellence

Price per night from

$408

Responds fast!
avg. 2 hours 25 minutes

Price per night from

$408

17

Club Bamboo South 223

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

1 4 7 nights min

  • 1 bedroom
  • sleeps 4
  • 7 nights min
  • Swimming pool
  • Car not necessary

Price per night from

$228

Responds fast!
avg. 2 hours 5 minutes

Price per night from

$228

(9) Excellent 

26

Blue Bayou

Anna Maria Island / Holmes Beach

Holmes Beach apartment

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Air conditioning
“"Home from Home"” A very well appointed apartment in a great location that had everything you would wish for to enhance your vacation experience. A real home from home that is clean, well furnished and spacious. The owners have been great to deal wi
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Price per night from

$144

Price per night from

$144

29

Runaway Bay 248

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly

Price per night from

$148

Price per night from

$148

34

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

Anna Maria Island / Anna Maria

Anna Maria house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$187

Price per night from

$187

(1) Excellent 

37

Charming house with private heated pool, patio, and grill - steps from beach

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$237

Price per night from

$237

29

NEW! Holmes Beach Home w/ Pool - Steps to Beach!

Anna Maria Island / Holmes Beach

Holmes Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning

Price per night from

$296

Responds fast!
avg. 10 minutes

Price per night from

$296

35

Breezy canalfront home w/ pool & dock - 3 blocks to Bean Point Beach!

Anna Maria Island / Anna Maria

Anna Maria house

3 8 min stay varies

  • 3 bedrooms
  • sleeps 8
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$303

Price per night from

$303

(1) Excellent 

13

AnnaMariaIsland a Paradise. MINUMIM RENTAL 2 WEEKS

Anna Maria Island / Bradenton Beach

Bradenton Beach apartment

2 5 14 nights min

  • 2 bedrooms
  • sleeps 5
  • 14 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$172

Price per night from

$172

27

Gulf-front condo w/ balcony & shared heated pool - steps to the beach & trolley!

Anna Maria Island / Holmes Beach

Holmes Beach house

2 6 7 nights min

  • 2 bedrooms
  • sleeps 6
  • 7 nights min
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$146

Price per night from

$146

(4) Excellent 

30

90 steps to the Beach!

Anna Maria Island / Holmes Beach

Holmes Beach condo

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“Amazing” Absolutely loved our stay! Beautiful condo right next to the beach. Had everything we needed! We will definitely be back!
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Price per night from

$196

Price per night from

$196

(6) Excellent 

23

Blue Heron Waterfront House Anna Maria island

Anna Maria Island / Anna Maria

Anna Maria house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly

Price per night from

$286

Responds fast!
avg. 2 hours 8 minutes

Price per night from

$286

(9) Very Good 

26

Bermuda Bay Club betwn the Beach and Bay , elevator, nicely furnished

Anna Maria Island / Bradenton Beach

Bradenton Beach house

3 6 7 nights min

  • 3 bedrooms
  • sleeps 6
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 ar
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Price per night from

$206

Responds fast!
avg. 3 hours 20 minutes

Price per night from

$206

(5) Average 

26

Anthony Beach Cottages Island Retreat

Anna Maria Island / Holmes Beach

Holmes Beach house

4 8 3 nights min

  • 4 bedrooms
  • sleeps 8
  • 3 nights min
  • Swimming pool
  • Child Friendly
  • Air conditioning
“Family friendly” My family and I enjoyed our stay in Florida and we all loved being able to be under one roof again. My mothers dream was to take us 6 kids, now adults, to the ocean again. Also, she wanted her two new grand-sons to see the ocean fir t
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Price per night from

$345

Responds fast!
avg. 2 hours 57 minutes

Price per night from

$345

46

Upscale tropical getaway with private pool, hot tub, elevator, and more!

Anna Maria Island / Holmes Beach

Holmes Beach house

3 6 min stay varies

  • 3 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$298

Price per night from

$298

(8) Very Good 

30

Runaway Bay - Bradenton Beach - Bay View Unit 193

Florida / Anna Maria Island

Anna Maria Island condo

2 5 7 nights min

  • 2 bedrooms
  • sleeps 5
  • 7 nights min
  • Beach / lakeside relaxation
  • Swimming pool
  • Child Friendly
“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 righ
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Price per night from

$131

Responds fast!
avg. 34 minutes

Price per night from

$131

37

Charming, dog-friendly duplex with a shared pool and a Key West-style deck!

Anna Maria Island / Bradenton Beach

Bradenton Beach house

2 6 min stay varies

  • 2 bedrooms
  • sleeps 6
  • min stay varies
  • Swimming pool
  • Child Friendly
  • Car not necessary

Price per night from

$42

Price per night from

$42