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$93

2 BR / 2 BA / Sleeps 6

The Seashell Cottage - Anna Maria vacation rentals
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$93

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The Seashell Cottage

2 BR / 2 BA / Sleeps 6 | Quick view

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Steps to the beach - "Old Florida" beach cottage located at 118 Palmetto Avenue, Anna Maria, Anna Maria Island, FL -- (2) Bed: (2 ) Bath: Accommodates up to (6) people: 1 King, 2 twins, 1 queen sleeper: Wireless : free long distance phone in the USA and enhanced cable channels. No smoking: Pets welcome Adorable two…
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$138

2 BR / 2 BA / Sleeps 4

1 Reviews

$138

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Holly Hideaway-730 Holly Road

2 BR / 2 BA / Sleeps 4 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Welcome to "Holly Hideaway" located on the northern end of beautiful Anna Maria Island. This lovely two bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool located in the back of the yard. You will …
  • Shared outdoor pool (unheated)
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(1)

Holly Hideaway- a private paradise

Left on May 16, 2013 for a stay in April 2013

This house was a little treasure! The living and kitchen area were spacious and well laid out. There was plenty of room for two couples to relax and feel comfortable. We really enjoyed bringing food in and eating at the large table on the screen porch! The second bedroom was fairly small, which wasn't really a problem for us since we don't spend any time there except to sleep. But for my …

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$159

3 BR / 2 BA / Sleeps 8

9 Reviews

$159

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Harmony House-779 Jacaranda Rd

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 9 Reviews

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Reviews

(9)

What a special place! Remember days gone by in this Key West style island getaway with sparkling pool in a tropical paradise setting. Spacious three bedroom plus den and two bath vacation rental home in desirable Anna Maria City. This property is close to everything including the azure gulf waters, pristine white…
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(9)

We keep coming back!

Left on Jul 25, 2008 for a stay in June 2008

We have stayed at this house four times in the last three years and would love to go back every chance we get. It is beautiful, comfortable, clean and has all you need at a home away from home. The location is perfect: minutes from the beach but completely away from traffic. We will be back soon!

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$79

2 BR / 1 BA / Sleeps 6

414 A Magnolia - Anna Maria vacation rentals
1 / 11

$79

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414 A Magnolia

2 BR / 1 BA / Sleeps 6 | Quick view

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This newly remodeled two bedroom duplex is situated halfway between the Gulf of Mexico and the Tampa Bay. Not more than 3 blocks in either direction. It is located on the north end of Anna Maria Island on Magnolia Avenue. The duplex is furnished with Tommy Bahama style furniture which offers a rich and comfortable …
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$189

3 BR / 2 BA / Sleeps 8

3 Reviews

$189

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Bikini Bottom-213 Periwinkle

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 3 Reviews

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Reviews

(3)

Tropical three bedroom and two bath large beach vacation rental cottage completely renovated with everything new. The brand new pool is a tropical paradise with a spa, a small wading area great for the little ones and a shuffle board court, too! The large open floor plan of living room, Florida room, kitchen and …
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(3)

It was AWESOME!!!

Left on Jul 10, 2014 for a stay in June 2014

Bikini Bottom was the BEST house we have every stayed at! Everything was clean and just perfect. It really felt like home. My husband and I have 3 girls and this house was so WONDERFUL for us! We will be back. Thanks for the dream vacation!!

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$68

2 BR / 1 BA / Sleeps 4

2 Reviews

$68

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316 Hardin A

2 BR / 1 BA / Sleeps 4 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. This home has been decorated to make you feel like you were in Key West. The living room offers an open floor plan to the kitchen to enjoy the family during your stay. The comfy …
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(2)

Outstanding furnishings and superb ventilation

Left on Apr 14, 2011 for a stay in March 2011

As a late arrvial, we had no personal interaction with Island Rental. Key pick-up works fine. Nice to be trusted.
The funishings far exceeded our fears/expectations. No cast-off furnishings. Screened in porch was favorite spot. Great cross ventilation. Kitchen worked very well and lacked nothing. Did purchase a good knife and cutting board (and a Keurig coffee maker.) Kudos for having …

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$68

2 BR / 1 BA / Sleeps 4

1 / 10

$68

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Sand Dollar Cottage-738NShore

2 BR / 1 BA / Sleeps 4 | Quick view

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This Island holiday home with easy access to the Gulf of Mexico and colorful sunsets. Two bedroom and one bath vacation rental in a desirable north end of Anna Maria location. It is also just a flip-flop walk to the pristine gulf beaches. Pet friendly and wireless internet There are so many island activities you …
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$180

3 BR / 2 BA / Sleeps 6

1 / 30

$180

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Heavenly Holly-721 Holly Road

3 BR / 2 BA / Sleeps 6 | Quick view

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Welcome to 721 Holly Road located on the northern end of beautiful Anna Maria Island. This lovely single family elevated three bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool & spa overlooking …
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$124

2 BR / 2 BA / Sleeps 7

8 Reviews

$124

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Sea's the Day - 207 Coconut

2 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 8 Reviews

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Reviews

(8)

The various shades of blue throughout 207 Coconut might be a bit misleading since you'll feel anything but during your stay in it. But then again, this is the water lover's dream vacation cottage. You have the option of swimming in either natural or manmade beauty. The beach is located less than 100 steps away, but …
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(8)

Vacation in Paradise

Left on Dec 03, 2009 for a stay in August 2009

Our family has vacationed on the west coast of Florida - Longboat Key and Anna Maria - for almost 30 years. Our stay at 207 Coconut was, by far, one of the best vacation experiences we have ever had. For one thing, Anna Maria is definitely the perfect beach destination, and Coconut fit our family's needs and expectations to a "T". We were thrilled at its location and ambiance and the pool was …

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$141

3 BR / 2 BA / Sleeps 6

2 Reviews

$141

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Down by the Sea-268 Gladiolus

3 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 2 Reviews

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Reviews

(2)

This lovely ground level vacation rental home -- three bedrooms and two full baths private home in a quiet Anna Maria City neighborhood. Beautiful tropical setting with a brand new heated salt water pool. Lovingly and locally decorated to make you feel right at home! Walking distance to the pristine white sand …
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(2)

Cozy comfy great time

Left on Jul 20, 2014 for a stay in July 2014

Gladiolus on Anna Maria was super comfortable for a great family vacation. A good living area, a big dining table for all of us, a garage spot, a private pool, and comfortable kitchen and rooms. We had enough privacy and space for all of us plus plenty of open space for us to feel connected. The location was great for walks to the pier, bike rides to Pine Ave (shops), and quick access to the …

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$140

4 BR / 3 BA / Sleeps 10

1 Reviews

$140

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Peony House-405 Spring Ave

4 BR / 3 BA / Sleeps 10 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Welcome to Peony House! This brand NEW, custom-built, elevated vacation rental home features four bedrooms, three baths, a large living room, and a dining room area for entertainment. From the moment you walk through the front door into this light and airy house, you will be happy that you chose Peony House. The large…
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(1)

Ami

Left on Aug 07, 2014 for a stay in August 2014

The house was awesome. The only thing that could have been better was the location on the island. It wasn't a far walk from the beach but most other things were a little out of the way. The island was great thou and I would definitely recommend Rudy's sub shop and mr. Bones BBQ. They were our favorites.

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$286

2 BR / 1 BA / Sleeps 6

1 / 16

$286

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Sea Grape Lane - 103 Seagrape

2 BR / 1 BA / Sleeps 6 | Quick view

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DIRECT GULF FRONT cottage in City of Anna Maria. This totally remodeled vintage beach cottage is located directly on the beautiful white sand beaches on Anna Maria island. As you can see, the cottage faces west on one of the best rated beaches in the world by several travel magazines. This ground level cottage,(no …
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$114

3 BR / 2 BA / Sleeps 7

2 Reviews

$114

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620 Rose Street

3 BR / 2 BA / Sleeps 7 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

This lovely elevated vacation rental home features three bedrooms, two baths and a large living/dining room area for entertainment. The large screened lanai off the living room makes a pleasant place for morning coffee, evening meals or just sitting back, relaxing and reading. The lush enclosed garden below has …
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(2)

Wonderful Retreat

Left on Apr 28, 2009 for a stay in March 2009

This was such a relaxing expereince to be at this home. The screened porch just added so much to the home and we all loved it. The location was perfect and we were able to walk to restaurants and stores. It was very quiet and serence. The garden was lush and lovely. We hope to return next year.

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$105

2 BR / 2 BA / Sleeps 6

1 / 12

$105

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Sea 'Esta - 890 North Shore

2 BR / 2 BA / Sleeps 6 | Quick view

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Welcome to Sea 'Esta, located at 890 North Shore and enjoy this upscale designer home. Your beach access is a short stroll away and easy walk to the Rod N Reel Pier.Enjoy the feel of old Florida in this nicely furnished 2 bedroom 2 bath vacation rental get away. This is a desirable location is well sought after with …
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$100

3 BR / 2 BA / Sleeps 8

4 Reviews

$100

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Maple Cottage-120 Maple

3 BR / 2 BA / Sleeps 8 | Quick view
“ Very Good ” 4 Reviews

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Reviews

(4)

Great ground level home on Maple Ave in Anna Maria CIty. West of Gulf Drive with no busy roads to cross. Three bedrooms and two baths. Extra bonus sun room off new deck perfect for a cookout. Kitchen is large enough to try your hand at island cusine, yet the Sandbar Restaurant is just up the street as well! …
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(4)

One of our best family vacations ever!

Left on Jul 24, 2008 for a stay in June 2008

We had a wonderful time during our vacation to AMI. One of the things that made our vacation so enjoyable was our unit. With 3BRs, a huge kitchen, top of the line decor and tons of living space the condo was definately top notch. The beach was absolutely beautiful and the trolley made getting around the island easy. We definately plan to return for another wonderful vacation next year. The Atwell…

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$136

3 BR / 2 BA / Sleeps 6

1 / 19

$136

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Casa Campoamor 11107 Gulf Dr.

3 BR / 2 BA / Sleeps 6 | Quick view

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Steps to the beach - "Old Florida" beach cottage located at 11107 Gulf Drive, Anna Maria, Anna Maria Island, FL -- (3) Bed: (2 ) Bath: Accommodates up to (6) people: 2 Kings 1 Queen, Adorable three bedroom and two bath beach cottage rental so close to the beach you can smell the salt air. The sugar sand beach is only…
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$192

3 BR / 2 BA / Sleeps 8

7 Reviews

$192

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Willow Cottage - 108 Willow

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 7 Reviews

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Reviews

(7)

Welcome to Willow Cottage located West of Gulf Dr at 108 Willow and on beautiful Anna Maria Island.This lovely ground level Anna Maria Island beach bungalow awaits you for the vacation you deserve! This rental home is stylishly decorated with touches of both new and old Florida. Rare and highly desirable three bedroom…
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(7)

Fabulous relaxing getaway!

Left on Jul 24, 2008 for a stay in June 2008

The house on Willow Ave. was the cutest little house on the outside. Once you get inside, however you discover a very spacious home. The backyard was wonderful with a bbq, lawn chairs, and the most beautiful smelling flowering tree. It took us only 2 minutes to walk from the front door of the house to the clear warm water of the beach. The house was stocked with EVERYTHING you could possibly need…

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$215

3 BR / 2 BA / Sleeps 8

1 / 15

$215

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Sweet Retreat Cottage-748 NoSh

3 BR / 2 BA / Sleeps 8 | Quick view

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Right across from the beach! This new ground level home awaits you and your family for a wonderful vacation. Enjoy everything from the heated pool to the soft sand beaches of Anna Maria Island. Everything is new and top of the line for your all of your holiday needs. This is a well sought after location on the quiet …
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$178

3 BR / 2 BA / Sleeps 6

1 / 34

$178

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La Vie en Rose 616 Rose St

3 BR / 2 BA / Sleeps 6 | Quick view

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Welcome to "La Vie en Rose"" located at 616 Rose Street on the northern end of beautiful Anna Maria Island. This lovely three bedroom and two bath vacation rental features all that you will need to stay a week or a month! Feel the breezes through the screened lanai or lounge by the new heated pool located in the back …
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  • Suitable for children - ask
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$132

3 BR / 3 BA / Sleeps 7

1 / 25

$132

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Sangria Sunrise 506 SoBay Blvd

3 BR / 3 BA / Sleeps 7 | Quick view

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Directly on beautiful Tampa Bay and views of the Sunshine Bridge makes this the picture perfect vacation rental. "Sangria Sunrise" Cottage is a 3 bedroom 3 bathroom ground level single family home in the City of Anna Maria. The bay front patio is perfect for soaking up the sun and you have your own slice of bay beach …
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$429

5 BR / 4 BA / Sleeps 12

2 Reviews

$429

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My Sisters Beach House

5 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

Welcome to "My Sister's Beach House" located at 520 Bayview Place on beautiful Anna Maria Island, Florida. This luxurious home has just been all updated and welcomes the vacationers who want to make their time on our beautiful island a wonderful experience. This luxury vacation rental is located on the highly …
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(2)

Blended family getaway!

Left on Jun 29, 2014 for a stay in June 2014

This was our first family trip so it was important that it be perfect and it was! There was plenty of room for all of our grown children and their spouses and grandchildren. The pool was wonderful and the game room was utilized every evening! There were several chefs among us and the kitchen did not disappoint. Everything was supplied and the table was large enough for everyone! We will …

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$136

3 BR / 2 BA / Sleeps 9

1 Reviews

$136

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Sandy's Getaway-122 Peppertree

3 BR / 2 BA / Sleeps 9 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Three Bedroom elevated recently renovated private home. This property in Anna Maria City and West of Gulf Drive! Gorgeous outdoor elevated covered deck is a perfect spot to relax and let your cares be whisked away by the Gulf Breezes. Just a few hundred steps from the Gulf of Mexico with no streets to cross. Just …
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(1)

Anna Maria Island - A Fantastic Summer Destination

Left on Jul 15, 2014 for a stay in July 2014

Where do I start! First, if you live anywhere near central Florida, this is one of those magical FL west coast places you must visit. A little, secluded, but quaint paradise just a couple hours away from Orlando. Second, the beaches are second to none; white sugar-like sand with a perfect relaxed shore, ideal for bathing and just relax. This time of year, the water is WARM - about 80F on average…

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$200

5 BR / 8 BA / Sleeps 10

1 / 22

$200

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The Palms - 810 NShore Dr

5 BR / 8 BA / Sleeps 10 | Quick view

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Welcome to "The Palms," a large and spacious Island holiday home with views of the Gulf of Mexico and colorful sunsets. Relax in a five bedroom and 3 1/2 bath vacation rental at the desirable northern end of Anna Maria. It is just a flip-flop walk to the pristine gulf beaches. The Bean Point beach access is right out …
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$134

2 BR / 2 BA / Sleeps 5

1 Reviews

$134

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Mangrove Cottage-105 Mangrove

2 BR / 2 BA / Sleeps 5 | Quick view
“ Terrible ” 1 Reviews

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Reviews

(1)

Mangrove Cottage Welcomes You! A charming two bedroom, two bath vacation rental home only one house from the sandy beach of Anna Maria Island on the Gulf of Mexico. Mangrove Cottage is very comfortable, bright and decorated for relaxed tropical living. Should you desire to lounge waterside in the comfort of your …
  • Shared outdoor pool (unheated)
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(1)

Absolutely disappointing. Dated, uncomfortable, poorly designed, run down!

Left on Nov 08, 2014 for a stay in November 2014

We have stayed in 6 places on the Island over the past 6 years. This is absolutely the worse place we have seen. The pictures are very misleading. The pool is at the back of the house, with no way to it except to go out the side door and all the way around the back. The inside of the house is awful, dated, and very run down. The "living" room has one very uncomfortable couch and 2 other …

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$258

4 BR / 3 BA / Sleeps 8

1 / 35

$258

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Living The Dream 703 So Bay

4 BR / 3 BA / Sleeps 8 | Quick view

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"Living The Dream" is a spacious 2,650 sq. ft. luxurious private vacation rental home with an attached 1 car garage and has been recently re-modeled with ALL NEW furnishing throughout. This 4 bedroom, 3 bath island home sleeps 8 comfortably with new Stearns & Foster and new Sealy Posturpedic mattresses. The bedrooms…
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$360

3 BR / 8 BA / Sleeps 6

6 Reviews

$360

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619 Rose - Dream Maker

3 BR / 8 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

Absolutely stunning in every way! This ultimate luxury beach vacation rental home is for relaxing with family and friends at the highly coveted north end of Anna Maria Island. It's just a short stroll from Bean Point beach and an easy walk to the Rod & Reel and City piers for fishing, dining or strolling. This …
  • Shared outdoor pool (unheated)
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(6)

Really liked this house

Left on Oct 08, 2009 for a stay in March 2009

Our family really enjoyed this house. The house was very comfortable - all
the furnishings were new and we really like the way it was decorated -
beachy but not overdone. The kitchen was well equipped - good
appliances, large fridge and plenty of storage. The beds were very
comfortable and it was very convenient that each bedroom had its own
washroom and tons of closet space . The salt …

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$319

4 BR / 3 BA / Sleeps 10

1 / 23

$319

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SeaDreams - 721 North Shore Dr

4 BR / 3 BA / Sleeps 10 | Quick view

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Enjoy fantastic sunsets and views of the aqua blue waters of the Gulf of Mexico from this 4 bedroom 3 bath Anna Maria City vacation rental home. Enjoy the best location on Anna Maria Island, on the north end. The quiet relaxing location allows you to listen to your cares get swept away by the balmy Gulf of Mexico …
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$132

2 BR / 2 BA / Sleeps 8

1 Reviews

$132

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Grant's View - 412 S Bay Blvd

2 BR / 2 BA / Sleeps 8 | Quick view
“ Poor ” 1 Reviews

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Reviews

(1)

This bay front private home is on Tampa Bay and you will enjoy the views of the water not to mention Dolphins swimming by. The bayfront is furnished with beach style furniture which offers a rich and comfortable atmosphere and is fully furnished with all comforts of home for a worry-free holiday; virtually everything…
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(1)

Location the only good thing

Left on Nov 03, 2014 for a stay in October 2014

This house has great location and that's about it. Sorry to say the place needs updating, needs to have more furnishings,like dishes and pots and pans etc....furniture was cheap and old. The place smelled musty and had cockroaches, dead and alive. No hot water in master shower and the shower door was about to fall off the track. Outlet in bedroom was hanging out of the wall and the cleaning crew…

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$250

3 BR / 4 BA / Sleeps 8

1 / 35

$250

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HoneyWood House 243 Willow

3 BR / 4 BA / Sleeps 8 | Quick view

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Living at the beach is like living anywhere else except it's BETTER in almost every way imaginable! You will enjoy the morning sun as it rises over the dock & canal and floods the living room with light. Experience it for yourself in 243 Willow Ave, Anna Maria Island. This beautiful 3 bedroom, den and 4 full …
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$114

3 BR / 2 BA / Sleeps 8

1 / 21

$114

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North Shore Cottage-871 NShore

3 BR / 2 BA / Sleeps 8 | Quick view

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Welcome to 871 No Shore guest cottage. Enjoy the feel of "old Florida" with this charming split level 3 bedroom 2 bathroom accommodations located behind the main house. Great bayfront location with direct access to bay. Feel free to walk along the main house with easy access to the Bay beach on Tampa Bay. This …
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$211

2 BR / 2 BA / Sleeps 6

1 / 43

$211

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A Sassy Seahorse 264 Gladiolus

2 BR / 2 BA / Sleeps 6 | Quick view

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The special "North End" vacation rental is immaculately clean and whimsically decorated, professionally landscaped, and boasts one of the larger pools and larger backyards on the Island. The spa is accented by iridescent glass. The 20' tall Chickee (tiki) hut was hand-built by Native Americans and houses the bar and …
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$143

2 BR / 2 BA / Sleeps 6

1 / 12

$143

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Garden Cottage-420 Spring Ave

2 BR / 2 BA / Sleeps 6 | Quick view

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Welcome to "Garden Cottage" located in the heart of Anna Maria City. Enjoy this charming island cottage and you will enjoy all that the island has to offer. Stroll to dining and all the new shops on Pine Ave. Just a short stroll and you will be at the City Pier where you can catch your own dinner and enjoy the views …
  • Internet Access
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$200

3 BR / 2 BA / Sleeps 8

1 / 19

$200

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Anna Maria Chateau

3 BR / 2 BA / Sleeps 8 | Quick view

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Anna Maria Chateau 612 Fern Street Anna Maria, Fl 34216 Perfect island getaway, nestled at the North end of Anna Maria Island. Anna Maria Chateau, open and spacious, a newly and completely renovated, well equipped 3 bedroom, 2 bath home with vaulted ceilings in the living area and in all bedrooms. This house has …
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    $214

    4 BR / 3 BA / Sleeps 8

    1 / 17

    $214

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    Sundown South

    4 BR / 3 BA / Sleeps 8 | Quick view

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    Sundown South 300 N. Shore Unit A Anna Maria, Fl. 34216 This is a one of a kind brand new construction on Anna Maria Island. Sundown South has 4 bedrooms and 3 full baths and a private heated pool. Located on a beautiful lake on the prestigious North Shore Drive and only a very short walk to famous Pine Ave. It…
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
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    $294

    3 BR / 2 BA / Sleeps 8

    1 / 26

    $294

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    Paradise Pointe 411 Poinsettia

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    Paradise Pointe located in the quiet north end of beautiful Anna Maria awaits the vacationer in you. This picture perfect ground level three bedroom two bathroom vacation rental single family home is located on a lagoon canal and has a private heated pool & spa. Also, it is about 2 blocks to the Bean Pt and the best …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Parking
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $214

    3 BR / 2 BA / Sleeps 6

    1 / 23

    $214

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    Havana Cay

    3 BR / 2 BA / Sleeps 6 | Quick view

    Details

    Havana Cay 109 Cedar St. Anna Maria, Fl. 34216 With this secluded and historic property, you will feel like you are vacationing at your own private 5-star resort. Havana Cay sits only 4 houses in from the beach and there are no busy streets to cross and zipping to and from the beach will be so easy! A quick 30 …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $350

    5 BR / 3 BA / Sleeps 15

    1 / 31

    $350

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    Lighthouse Lagoon

    5 BR / 3 BA / Sleeps 15 | Quick view

    Details

    Lighthouse Lagoon 508 Spring Avenue Anna Maria, Fl. 34216 Lighthouse Lagoon is a beautifully updated 5 bedroom, 3 bathroom Island home located on Spring Street on the North-end of Anna Maria Island. The rear of the house backs up to outstanding Pine Avenue with it's quaint shops, wonderful restaurants and of …
    • Private Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $145

    4 BR / 2 BA / Sleeps 8

    2 Reviews

    $145

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    Whispering Winds

    4 BR / 2 BA / Sleeps 8 | Quick view
    “ Excellent ” 2 Reviews

    Details

    Reviews

    (2)

    Whispering Winds 210 Sycamore Avenue Anna Maria, Fl 34216 Key West style 4 bedroom, 2 bath home just a short walk from the Gulf of Mexico. This home offers private heated pool, three covered decks overlooking pool, BBQ grill, two car garage, cathedral ceilings, tile, carpet, open floor plan with large kitchen…
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (2)

    Can't wait to go BACK!

    Left on May 13, 2014 for a stay in March 2014

    We stayed at Whisper Winds,3 houses to the wonderful White Sand... Great house with 4 bdrm ,heated pool, great location with plenty of room for Family Vacation.. This is our 2nd trip to AnnaMaria. So many quaint shops,be sure you visit the fresh donuts shop..get their early their worth the wait. The north end is great if your traveling with small kids. Bring your bikes or rent them their.. So …

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    $243

    2 BR / 2 BA / Sleeps 4

    4 Reviews

    $243

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    Wave Crest: 2BR Gulf-Front Beachfront Cottage

    2 BR / 2 BA / Sleeps 4 | Quick view
    “ Excellent ” 4 Reviews

    Details

    Reviews

    (4)

    This gulf-front vacation rental cottage is located right on the beach on the secluded north end of Anna Maria Island. Step out Wave Crest's door and into the waiting lounge chairs and rub your toes in the beautiful white sand beaches of AMI or enjoy the views of the sparkling Gulf of Mexico waters from the Florida …
    • Waterfront
    • Ocean or water views
    • Wireless Internet
    • Washing Machine
    • Clothes Dryer
    • Suitable for children - over five
    • Suitable for the elderly

    Details

    Reviews

    (4)

    Best kept secret in the country

    Left on Jul 14, 2013 for a stay in March 2013

    If you want the beach as your back yard, along with a quiet and empty beach, you just found it. This house was perfect for my wife and I and our two daughters. Having been to Mexican all inclusive resorts twice, my daughters said they actually enjoyed this more. It was so relaxing and being able to look at the beach and water before bed and we woke up was incredible. The sand is so fine, you won'…

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    $200

    2 BR / 2 BA / Sleeps 6

    1 / 20

    $200

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    A Sandbox by the Sea

    2 BR / 2 BA / Sleeps 6 | Quick view

    Details

    A Sandbox by the Sea 507 Spring Avenue Anna Maria, FL 34216 A Sandbox by the Sea has a large luxurious tropical yard with a new private heated pool complete with tanning shelf and a bubbling spa tub!! Both water features have the option of digital light shows for evening fun! A press of a button allows you to …
    • Heated Pool
    • High Speed Internet
    • Patio
    • Television
    • DVD Player
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $209

    4 BR / 4 BA / Sleeps 8

    1 Reviews

    $209

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    Sunchase Villa

    4 BR / 4 BA / Sleeps 8 | Quick view
    “ Very Good ” 1 Reviews

    Details

    Reviews

    (1)

    Sunchase Villa 302 Gulf Blvd Anna Maria, Fl. 34216 Sunchase Villa is a true Old Florida, ground level beach cottage nestled on the north end of Anna Maria Island only a short walk to restaurants and shopping. There are fantastic Gulf Views from this well-appointed 4 bedroom, 4.5 bath private home directly across…
    • Internet Access
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (1)

    Great location but property needs some improvements

    Left on Dec 15, 2014 for a stay in December 2014

    The location of this house is great---right on the beach and close to many restaurants! The house is roomy and nicely furnished, including multiple TVs for anyone who is interested. The screened-in porch looking out on the water is a real plus! However, the house needs some serious work. Many of the windows did not open, the kitchen cabinet doors kept falling open, one bathroom drain was clogged…

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    $440

    6 BR / 3 BA / Sleeps 16

    1 / 57

    $440

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    Grande Haven-804 No Shore Dr.

    6 BR / 3 BA / Sleeps 16 | Quick view

    Details

    Grande Haven is a spectacular example of high architecture, fine design and custom finishing at its best. This home was designed by the award winning Gene Leedy, combining the use of pre-stressed concrete, contemporary architecture and a splash of British East Indies Island flavor. Leedy creates something truly …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Parking
    • Dishwasher
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $209

    4 BR / 3 BA / Sleeps 8

    1 / 30

    $209

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    Pelican Villa

    4 BR / 3 BA / Sleeps 8 | Quick view

    Details

    Pelican Villa 214 Magnolia Avenue Anna Maria, Fl. 34216 Pelican Villa is a newly constructed home on the prestigious north end of Anna Maria Island. You will find 4 bedrooms and 3 full bathrooms in this property. This building is an elevated home with a large covered patio area and a private heated pool, …
    • Outdoor Pool
    • Internet Access
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $128

    3 BR / 2 BA / Sleeps 8

    1 / 26

    $128

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    316 Hardin Ave

    3 BR / 2 BA / Sleeps 8 | Quick view

    Details

    This newly remodeled and updated island vacation rental duplex is just a stroll to the Gulf of Mexico and our beautiful sunsets. This home has been decorated to make you feel like you were in Key West. This unique unit is actually two separate living spaces that adjoin in the center. Offering two separate full …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Parking
    • Dishwasher
    • Pet friendly
    • Suitable for children - ask
    • Suitable for the elderly - ask

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    $260

    4 BR / 2 BA / Sleeps 10

    15 Reviews

    $260

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    Blue Heron Beach House

    4 BR / 2 BA / Sleeps 10 | Quick view
    “ Excellent ” 15 Reviews

    Details

    Reviews

    (15)

    ** Some Fall weeks as low as $1400 - grab your week now before the owner comes to his senses ** Steps to the beach - "Old Florida" large beach cottage located at 117 Peppertree Avenue, Anna Maria, Anna Maria Island, FL -- (4) Bed: (2 ) Bath: Accommodates up to (10) people: 2 King, 2 twins, 2 bunk bed, 2 queen …
    • Shared outdoor pool (unheated)
    • Internet Access
    • Parking
    • Dishwasher
    • Suitable for children - ask
    • Suitable for the elderly - ask

    Details

    Reviews

    (15)

    Slice of Paradise

    Left on Jul 24, 2008 for a stay in June 2008

    I like to start with thanking the Staff at Island Real Estate & Vacation Rentals, even thought it was raining upon our arrival they turned it in to a Sunny Day in paradise. Their professional and friendly atmosphere felt at if I was at a Five Star, Five Diamond Island Resort. The pictures and description of the rental fall short of how comfortable and covenant it was to stay at the cozy home. …

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    $225

    4 BR / 2 BA / Sleeps 10

    1 / 15

    $225

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    Cabana Breeze

    4 BR / 2 BA / Sleeps 10 | Quick view

    Details

    Cabana Breeze 511 Spring Avenue Anna Maria Island, Fl 34217 Cabana Breeze is a newly and completely renovated 4 bedroom 2 bathroom home with multiple outdoor shaded living areas, a large lot, and a brand new custom pool and pool-side cabana. This gorgeous home is located on the prestigious north end of Anna Maria …
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $250

      4 BR / 3 BA / Sleeps 10

      1 / 22

      $250

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      Bay View

      4 BR / 3 BA / Sleeps 10 | Quick view

      Details

      Bay View 804 South Bay Blvd. Anna Maria, Fl 34216 Stunning Bay views and white sandy beaches are literally at your doorstep at Bay View. This spacious, well-equipped four bedroom, three-bath ground-level property provides all the comforts of home in an ideal beach setting. It has been recently completely …
      • Internet Access
      • Dishwasher
      • Suitable for children - ask
      • Suitable for the elderly - ask

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      $350

      5 BR / 4 BA / Sleeps 12

      1 / 28

      $350

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      Villa La Concha

      5 BR / 4 BA / Sleeps 12 | Quick view

      Details

      Villa La Concha 113 Maple Avenue Anna Maria, Fl 34216 Villa La Concha is a stunning brand new elevated and luxury Island home located on the prestigious Northern end of Anna Maria Island. This lovely home is located West of Gulf Drive and just 1 minute stroll down the street from a direct beach access to the Gulf …
        • Suitable for children - ask
        • Suitable for the elderly - ask

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        $121

        1 BR / 1 BA / Sleeps 4

        4 Reviews

        $121

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        Island Place Cottage: 1BR Pet-Friendly Cottage

        1 BR / 1 BA / Sleeps 4 | Quick view
        “ Excellent ” 4 Reviews

        Details

        Reviews

        (4)

        This vacation rental is located on Anna Maria Island's historic Pine Avenue, halfway between the Gulf of Mexico and the Anna Maria City Pier! This adorable, one bedroom cottage, with high beamed ceilings, wood floors and shabby chic d├ęcor throughout is ideal for a vacation getaway! This quaint cottage offers a fully…
        • Internet Access
        • Washing Machine
        • Clothes Dryer
        • A/C or climate control
        • Parking
        • Pet friendly
        • Suitable for children - over five
        • Suitable for the elderly

        Details

        Reviews

        (4)

        Great cottage, great location.

        Left on Jul 26, 2013 for a stay in July 2013

        Cottage is perfectly located right in the heart of anna Maria. Quick walk to the Gulf beaches or to the Bay.

        Cottage was immaculate and perfect size for the three of us. A few years ago we stayed in the adjacent Pineapple House which was also perfect for our larger party during that visit.

        Would not hesitate to stay again.

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        $250

        3 BR / 3 BA / Sleeps 6

        1 Reviews

        $250

        Inquire

        Anna Maria Cottage

        3 BR / 3 BA / Sleeps 6 | Quick view
        “ Very Good ” 1 Reviews

        Details

        Reviews

        (1)

        Anna Maria Cottage 104 Magnolia Avenue Anna Maria Island, FL 34216 This beautiful historic beach cottage is a true embodiment of "Old Florida Charm". This wonderful home offers 3 suites, each with their own en-suite full bathroom, a wrap around porch with stunning Gulf views and much more! Just steps from the…
          • Suitable for children - ask
          • Suitable for the elderly - ask

          Details

          Reviews

          (1)

          Great location!

          Left on Feb 23, 2015 for a stay in February 2015

          I spent almost 3 weeks on AMI sharing this lovely cottage with my sister and some other friends and family. The location is wonderful, very close to the beautiful beach, so an easy stroll over for sunsets and long walks, and quite near the Sandbar and restaurants and shops on Gukf and Pine. The cottage is nicely decorated with vintage signs, historical photographs and local art, and the furniture…

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