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$68

2 BR / 1 BA / Sleeps 4

Sand Dollar Cottage-738NShore - Anna Maria vacation rentals
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$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 …
  • Internet Access
  • Parking
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(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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$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…
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(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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$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

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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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$141

2 BR / 1 BA / Sleeps 4

3 Reviews

$141

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TURTLE TRAX

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

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Reviews

(3)

This adorable remodeled duplex sits quietly in the highly desirable north end of the Island in the City of Anna Maria. It is a short walk of only a little more than a block to the Gulf beach where the sand is sugary white and the water is a beautiful blue-green color. There is a King in the master with TV, a Queen …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(3)

Great week at a great place

Left on Aug 08, 2013 for a stay in April 2013

We had a great visit in april. The weather was great, the pool was even better. Cannot wait to get back in 2014.

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$141

2 BR / 1 BA / Sleeps 5

YELLOWBIRD COTTAGE  A - Anna Maria vacation rentals
1 / 30

$141

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YELLOWBIRD COTTAGE A

2 BR / 1 BA / Sleeps 5 | Quick view

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Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private Washer/Dryer, Cable TV, …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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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 …
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(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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$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 …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(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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$93

2 BR / 2 BA / Sleeps 6

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$93

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The Seashell Cottage

2 BR / 2 BA / Sleeps 6 | Quick view

Details

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…
  • Internet Access
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$141

2 BR / 1 BA / Sleeps 5

1 Reviews

$141

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YELLOWBIRD COTTAGE B

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

Details

Reviews

(1)

Beautiful 2B/1B cottage on the quiet North end, only 5 houses to the beach, and no streets to cross. Beautiful new Heated Pool. Twins can be converted to King in all bedrooms. NO dishwasher, no garbage disposal.Rear trash pick up! Charcoal Grill, not gas. Both units also include private Washer/Dryer, Cable TV, …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Very close to the beach

Left on Aug 02, 2013 for a stay in June 2013

Excellent service, from booking to checking into Yellowbird B. The cottage was lovely and clean and had everything we needed to enjoy our stay, including chairs for the beach.
Brilliant location only a few steps from the lovely sandy beach.
Only negative bathroom although very clean could do with an update.
We had a fantastic holiday and hope to come back.

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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

Details

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 …
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$175

2 BR / 2 BA / Sleeps 6

6 Reviews

$175

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Blue Dolphin Inn - Heron Up

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

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Reviews

(6)

The Heron unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, two bath upstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki table. The Blue Dolphin…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

great location

Left on Mar 30, 2011 for a stay in March 2011

we enjoyed our second stay at the blue dolphin. the unit has a great floorplan, huge porch and was very nicely appointed and decorated. everything was new and comfortable, the kitchen had everything needed and every appliance. washer and dryer and most furniture new, unit was freshly painted and tastefully decorated. location was superb.

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$129

2 BR / 2 BA / Sleeps 6

1 / 25

$129

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Casa Nana

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Enjoy an old fashioned Florida beach vacation at this wonderful cottage just 4 houses from the beach! One Florida family has spent over four decades building happy summer memories right in this spot, and they invite you to create some of your own treasured moments on your next visit to Anna Maria. Located right in …
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Parking
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$79

2 BR / 1 BA / Sleeps 6

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 …
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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

Details

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 …
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(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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$150

2 BR / 1 BA / Sleeps 6

6 Reviews

$150

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Coral Cottage 2 BR in Anna Maria 1 Blk to Beach

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 6 Reviews

Details

Reviews

(6)

1940’s Classic beach cottage located at 9901 Gulf Drive Anna Maria, recently renovated, two bedrooms, one bath, with an eclectic, artistic decorating style that will bring a smile to your face and make your stay here a memorable experience. Located only five houses from the white, sugar sand beaches of the Gulf of …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Central heating
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(6)

Location Location Seriously Location!!!!

Left on Dec 09, 2013 for a stay in December 2013

TheLocation of this dog friendly cottage is awesome. It is right on Gulf drive, only a block from the beach (gulf side) and a few blocks from Tampa Bay. It is also very short walking distance from any local businesses you might need or want to visit (coffee shop, bars, restaurants, general store, sub shop, etc). The price was very reasonable. We were impressed with this size of the home & …

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$156

2 BR / 1 BA / Sleeps 6

9 Reviews

$156

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Blue Dolphin Inn - Skimmer Down

2 BR / 1 BA / Sleeps 6 | Quick view
“ Very Good ” 9 Reviews

Details

Reviews

(9)

The Skimmer unit at the Blue Dolphin Inn, located at 404 Alamanda in the Historic Village of Anna Maria is a wonderful two bedroom, one bath downstairs unit furnished in a tropical theme. The Blue Dolphin Inn consists of four units surrounding a free style heated pool with fountains and nearby tiki table. The Blue …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Grill
  • Pet friendly - ask
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(9)

relaxing

Left on Oct 01, 2010 for a stay in August 2010

great time ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok ok

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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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$186

2 BR / 2 BA / Sleeps 4

1 / 21

$186

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Tequila Sunset: 2BR Island Home with Heated Pool

2 BR / 2 BA / Sleeps 4 | Quick view

Details

This lovely two bedroom family- and pet-friendly Anna Maria Island vacation rental is just a few houses from the island's white sand beach and azure blue waters of the Gulf of Mexico. Located on the quiet north end of the island in the city of Anna Maria, at 950 square feet, this classic elevated beach home with both…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Pet friendly
  • Suitable for children - over five
  • Suitable for the elderly - ask

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$171

2 BR / 2 BA / Sleeps 6

4 Reviews

$171

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Island Oasis: 2BR Canal Home with Pool and Dock

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

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Reviews

(4)

Come and enjoy your own private Island Oasis! Located on the north end of Anna Maria Island in the city of Anna Maria, one block from the bay and a few blocks from the City Pier, this charming vacation rental will allow for some serious relaxation. This home-away-from-home offers two bedrooms and two baths, with a …
  • Waterfront
  • Spa/Whirlpool
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(4)

Best Stay Yet!

Left on Jul 11, 2013 for a stay in May 2013

We were lucky to find Island Oasis. The wife and I have visited Siesta Key and anna Maria Island several times. This was the best stay yet. We caught snook across the bay in Perico Bayou and grouper at Longboat Pass. The backyard pool is the nicest and being able to hop in the boat and to the beach is just wonderful.

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$143

2 BR / 2 BA / Sleeps 4

1 Reviews

$143

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Birds Eye View

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

Details

Reviews

(1)

Birds Eye View 802 Gladiolus Street Anna Maria, FL 34216 This spacious and charming 2 bedroom, 2.5 bath elevated home is just three houses from the Gulf of Mexico! It is located near popular Bean Point at the prestigious northern tip of Anna Maria Island. It has fabulous island style furnishings and a bright open …
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Nice Location - Bean Point

Left on Sep 06, 2013 for a stay in September 2013

Lovely property...close to both gulf and bay beaches for sunrise/sunset. Loads of space with a huge master bedroom/bathroom. Clean and well kept but could use a few updates. Toaster looked 1960's vintage and although it worked well enough, we were a bit concerned using it due to it's age. Oven door and oven itself were tricky to operate. Several of the venetian blinds did not work, either to open…

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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

Details

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 …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$223

2 BR / 2 BA / Sleeps 6

1 / 35

$223

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TRIPLEPLAY

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Looking for that place to kick back and relax your cares away? Check out ‘Triple Play Guest House.' There's a triple chance to play: (1) walk to the beach, (2) lounge in the pool or spa or patio or (3) launch a kayak, fish or just relax on one of our two docks on the canal. Nothing quite compares to the sugary white…
  • Hot Tub/Jacuzzi
  • A/C or climate control
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly

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$157

2 BR / 1 BA / Sleeps 6

7 Reviews

$157

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Pineapple Cottage: 2BR Quaint Pet-Friendly Cottage

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

Pineapple Cottage, centrally located on historic Pine Avenue in the city of Anna Maria, is the perfect place to slow down and catch your breath! This Anna Maria Island cottage is tastefully decorated with wood floors, granite and stainless kitchen, tiled shower and comfortable furnishings. The master bedroom boasts a…
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Porch
  • Pet friendly
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(7)

peaceful place

Left on Jul 25, 2013 for a stay in June 2013

I love aMI, I am a visitor since 2003 from Miami. I love, love this place and Pineapple Cottage was the best place for us to stay. I felt right at home with all the comodities anyone can desire. We thank you for sharing this house with us. See you soon.

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$175

2 BR / 2 BA / Sleeps 4

1 / 15

$175

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Windsong Cottage

2 BR / 2 BA / Sleeps 4 | Quick view

Details

Windsong Cottage 119 Beach Avenue Anna Maria, Fl 34216 Windsong Cottage is a charming 2 bedroom 2 bath elevated home just five houses from the Gulf. It has an open floor plan with new, comfortable furnishings that make you feel *right at home*. The plantation shutters add to that "Old Florida" charm. You won'…
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$190

2 BR / 2 BA / Sleeps 10

17 Reviews

$190

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Anna Maria Escape

2 BR / 2 BA / Sleeps 10 | Quick view
“ Excellent ” 17 Reviews

Details

Reviews

(17)

The Anna Maria Escape located at 725 North Shore Drive in Anna Maria city is just that - a peaceful, relaxed place to get away from it all. You can stroll on the beach for miles in either direction! It’s a perfect Anna Maria Island vacation home!This spacious and charming two bedroom, two bath Gulf front home has …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Grill
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

Details

Reviews

(17)

peaceful tranquilty

Left on Feb 23, 2009 for a stay in July 2007

No need to travel to paradise when it is right here in our own backyard. The Escape provided everything we needed and had plenty of room for our family of 6. We already know we'll be coming back to the Escape.

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$124

2 BR / 2 BA / Sleeps 6

1 / 13

$124

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Sunny Side Up

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Sunny Side-Up 267 Gladiolus Street Anna Maria, Fl. 34216 Trendy colorful, happy cottage located in popular Anna Maria City. This 2 bedroom 2 bath ground level home was completely renovated inside and out. All new furniture throughout with lots of fun decor and an island feel. A delight the moment you enter …
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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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

Details

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
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$157

2 BR / 1 BA / Sleeps 4

1 / 22

$157

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Heron - 706 Rose A

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Welcome to the Heron located at 706 Rose unit A. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits the vacationer in you. Recently updated and all new furniture throughout will accommodate up to 4 people. There is a queen bed, 1 twin bed and a queen …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$157

2 BR / 2 BA / Sleeps 6

1 / 24

$157

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Cook's Cove: 2BR Elderly-Friendly Steps From Beach

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Grab your flip flops and your bathing suit for your fabulous vacation in this well-appointed Anna Maria home! Cook's Cove is located just steps away from the beautiful, white sand beaches of Anna Maria Island and the azure water of the Gulf of Mexico. Both elderly- and family-friendly, this lovely, two-bedroom, 2.5-…
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

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$223

2 BR / 2 BA / Sleeps 6

4 Reviews

$223

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LAZY LAGOON

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Newly remodeled 2 bedroom/2 bath home. Brand new pool, hot tub, and landscape with a serene canalfront setting. Located on a quiet dead-end street, close to the trolley, the beach, and walking distance to Anna Maria shops and restaurants. Bring your boat and take part in some of the best fishing on the West Coast or …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(4)

friendly retreat

Left on Aug 14, 2013 for a stay in July 2013

This was our 3rd visit to the island. we usually
share with family but we travelled ourselves this
year. Lazy Lagoon was a beautiful 2 bed canal
home with pool. This smaller property offered
everything the larger homes we previously rented had.
My daughter (19) fished for hours every day even the
rain did not bring her in. A lovely walk to the short
walk to the beach and short walk to sand …

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$129

2 BR / 1 BA / Sleeps 4

2 Reviews

$129

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Light House: 2BR/1BA Canal-Front Home with Dock

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

Details

Reviews

(2)

The Light House welcomes you in with its tropical landscaping, canal view and calming green exterior. This nicely furnished two-bedroom, one-bath vacation rental on Anna Maria Island has everything you need to begin a relaxing and restful vacation. Newer appliances will make quick work of breakfast or dinner, leaving…
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(2)

Island Paradise

Left on Jan 07, 2014 for a stay in December 2013

One block from bay and four blocks from Gulf or Bean Point...what more could you want?!! Easy walk to all the restaurants and shopping on the North end of island (our favorite part of anna Maria). We brought our own bicycles and the garage was a good storage area for them.
Loved the backyard view of the canal and the Florida room was excellent for dining in on those occassions.
Cozy little …

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$128

2 BR / 2 BA / Sleeps 8

1 / 23

$128

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North Bay Hideaway- 809 North Bay Blvd, Anna Maria

2 BR / 2 BA / Sleeps 8 | Quick view

Details

The best of both worlds on the Island is where the Gulf meets the Bay at the "Tip" of Island in Anna Maria. Beautiful Sunsets, Fishing Piers, a Park and Bird Watching can be found at the Northern tip of the Island. This 2BR/2BA plus a Loft is located one property from the beach access at Bean Point. Peeks of the Gulf …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask
  • Wheelchair accessible - ask

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$157

2 BR / 1 BA / Sleeps 4

1 / 25

$157

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Dolphin - 706 Rose B

2 BR / 1 BA / Sleeps 4 | Quick view

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Welcome to the Dolphin located at 706 Rose unit B. This quaint 2 bedroom 1 bath duplex located on a quiet street on the north end of beautiful Anna Maria Island awaits the vacationer in you. Recently updated and all new furniture throughout will accommodate up to 4 people. There is a queen bed, 1 twin bed and a queen …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$95

2 BR / 1 BA / Sleeps 6

1 Reviews

$95

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414 B Magnolia

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

Details

Reviews

(1)

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. A new heated pool was just installed and only can be used by this unit. The home is furnished …
  • Shared outdoor pool (unheated)
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Neat duplex in an excellent location

Left on Nov 25, 2014 for a stay in October 2014

We usually book a house on Anna Maria a year in advance but this was a late booking, just for the two of us and we were not disappointed. The duplex was roomy, well equipped and the pool was an additional bonus. It's location was excellent, only a short walk to restaurants, shops and bars. And, more importantly to both piers which we love. We met the owner whilst we were there and he was a really…

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$179

2 BR / 1 BA / Sleeps 4

1 / 14

$179

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Moondance

2 BR / 1 BA / Sleeps 4 | Quick view

Details

Moondance 206 Spring Lane Anna Maria, Fl. 34216 If you are looking for a unique property you have found it! This property sits right out on the beach and has a private balcony from the property to the beach. Nestled in the heart of Anna Maria, Moondance offers quaint privacy but is only a very short walk over to …
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$186

2 BR / 2 BA / Sleeps 6

7 Reviews

$186

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Whispering Pines: 2BR Classic Cottage Near Beach

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 7 Reviews

Details

Reviews

(7)

This two-bedroom, two-bath vacation rental is located on the quiet north end of Anna Maria Island. Whispering Pines is just three houses from one of the most beautiful beach accesses on the island. This classic 1920's beach cottage has been lovingly restored. The original wood molding, fireplace, high ceilings, and …
  • Internet Access
  • Fireplace
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(7)

Perfect Old Florida

Left on Jul 25, 2013 for a stay in April 2013

Whispering Pines has everything you could possibly want in an aMI vacation rental home with the exception of swimming pool, but who needs a pool when you are fifty yards from beach access and the Gulf?

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$171

2 BR / 2 BA / Sleeps 4

4 Reviews

$171

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Simpatico: 2BR Pet-Friendly Canal Home with Kayaks

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

Details

Reviews

(4)

With its luscious landscaping, eclectic look and colorful Key-West style, Simpatico could be right out of Coastal Living Magazine. This bungalow is perfect for the ideal secluded island vacation! Located on the north end of Anna Maria Island, this canal home, with a boat dock and kayaks, is just a short stroll to the …
  • Waterfront
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(4)

A relaxing, tropical paradise...

Left on Apr 07, 2014 for a stay in March 2014

This cottage is the perfect getaway spot for those who want a tropical experience. Located on a canal, this home was bright, clean, and cheery and packed with tropical foliage that made us feel like we had escaped to the tropics. There is a great entertaining area and backyard which our friends loved! Coastal Cottages were terrific and extremely responsive when we called with questions during …

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$150

2 BR / 2 BA / Sleeps 8

1 / 8

$150

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Copacabana

2 BR / 2 BA / Sleeps 8 | Quick view

Details

Copacabana is a 2 bedroom, 2 bath private canal front home with a pool; with tile floors throughout and a designer's stylish touch, you will feel you have found your home away from home! Copacabana will accommodate 6-8 people and offers a separate family room with a large flat screen TV that is great for the kids. …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

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$223

2 BR / 2 BA / Sleeps 6

1 / 29

$223

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CHAMPAGNE SHORES

2 BR / 2 BA / Sleeps 6 | Quick view

Details

This great 2 Bed/2 Bath Home with Private Heated Pool resides in Anna Maria and is only one block to the beach and has no busy streets to cross to get there. You can quickly make your way to the Gulf Sands and to all of the great shops and restaurants that Anna Maria and Holmes Beach have to offer. Furnished very …
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly

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$115

2 BR / 1 BA / Sleeps 6

1 Reviews

$115

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Southern Breeze 1

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Southern Breeze #1 607 Fern Street #1 Anna Maria, Fl. 34216 ISLAND 6-PLEX - Newly renovated top to bottom June 2013! These are 2 bedroom, 1 bath ground level units located at the tip of Anna Maria Island just steps from the Bay. Heated pool with nicely landscaped surroundings. Each is decorated with the feel of…
  • Shared outdoor pool (unheated)
  • Internet Access
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Descoberta Maravilhosa!!

Left on Aug 21, 2014 for a stay in June 2014

Amei conhecer a ilha Anna Maria! tanto que estou pretendendo voltar no próximo ano para passar pelo menos um mês inteiro! Alugamos essa casa pela internet com poucos dias de antecedência, recebemos um código por email que serviu para abir um cofre na entrada liberando as chaves da casa. Tudo estava limpo, arrumado, ar condicionado ligado (estava bem quente!). Dois quartos bem mobilhados, uma …

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$150

2 BR / 2 BA / Sleeps 6

1 / 23

$150

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BLUE LAGOON SOUTH

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa. Sleeps 6. 708 Sq. ft. 76 …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

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$250

2 BR / 2 BA / Sleeps 4

2 Reviews

$250

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The Shady Mango ~ Anna Maria Island's Most Charming Coastal Cottage!

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

Details

Reviews

(2)

The Shady Mango was originally built in 1925. According to local history the heart pine used in constructing the original house came by steam boat to the City Pier and was hauled by horse-drawn lorry up Pine Avenue to the home's present site. In 2004 the home was given a major renovation consisting of replacing …
  • Hot Tub/Jacuzzi
  • Internet Access
  • Fireplace
  • Housekeeping Optional
  • Washing Machine
  • Suitable for children - ask
  • Suitable for the elderly

Details

Reviews

(2)

Magical!

Left on Apr 06, 2012 for a stay in April 2012

I've been affiliated with The Shady Mango for almost 4 years now, and not once have I had a guest stay there who didn't just love their experience! The cottage is just as charming as it looks in the pictures (one guest told me that of all the vacation rentals he and his wife have enjoyed, The Shady Mango is the only one that actually looks like its pictures!), and the back yard with its navy …

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$200

2 BR / 2 BA / Sleeps 6

4 Reviews

$200

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Starfish Dreams: 2BR Canal Home w/Dock and Pool

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 4 Reviews

Details

Reviews

(4)

Starfish Dreams is the perfect place to start your vacation! This family-friendly vacation rental is centrally located on Pine Avenue in the city of Anna Maria on Anna Maria Island, halfway between the Gulf of Mexico and Tampa Bay. If that were not enough, it also has a heated pool and is on a canal. This two-…
  • Waterfront
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children - over five
  • Suitable for the elderly - ask

Details

Reviews

(4)

Magnificent property in fantastic spot on Anna Maria

Left on Jun 14, 2013 for a stay in May 2013

This was the best holiday rental (sorry Sue) we've ever had. Right in Pine Street, where all of the boutiques and local stores are, but within 100 yards of the beach and City Pier. Fantastically appointed, with excellent quality of all the equipment, this is a really, really comfortable and well situated property.

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$150

2 BR / 2 BA / Sleeps 6

1 Reviews

$150

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BLUE LAGOON NORTH

2 BR / 2 BA / Sleeps 6 | Quick view
“ Very Good ” 1 Reviews

Details

Reviews

(1)

Completely remodeled 2 bedroom/2 bath duplex, with a beautiful tropical HEATED pool, just over a block to the beach, and the free island Trolley! There is a King and a Queen bedroom in the North Unit, and a King and Twin Bedroom in the south unit. Both units also have a queen sleeper sofa.. 708 Sq. ft. 76 North …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great Location

Left on Dec 31, 2014 for a stay in October 2014

BLN is very well located in the quieter northern part of the island. It is just a very short walk from the beach and Ginny and Jane Es. Likewise, a short walk in the opposite direction to the shops and restarants on Pine. The unit itself, while it doesn't look anything special from the outside, is very pleasant on the inside and surprisingly spacious, but don't expect 5 star luxury.

One note …

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$125

2 BR / 2 BA / Sleeps 6

1 Reviews

$125

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Star Fish Cottage-209 Palm Ave

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

When a starfish wants to get away, it's more than happy to just detach an arm and take time to recuperate. This elevated coastal cottage might be worth giving up an arm, but we can skip that part and just focus on you relaxing. Located just east of Gulf Drive, a scenic 200-yard walk will take you right to the sugar-…
  • Internet Access
  • Parking
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Perfect place to relax.

Left on Jul 18, 2014 for a stay in May 2014

I found the Star Fish Cottage in Anna Maria online and was enamored by the pictures and location. The cottage is all it promised to be and then some. A short walk to the beach, and close to local stores and restaurants. When I arrived the place was immaculate. Everything is there that you will need to enjoy a quiet, relaxing vacation. Just bring your clothes and personal items. Everything else…

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$189

2 BR / 2 BA / Sleeps 6

1 Reviews

$189

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Sapphire Surf - Heated Pool, North End, 1 Level

2 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Enjoy the quiet and comfort of SAPPHIRE SURF on the North end of Anna Maria Island. This enchanting two bedroom/two bath ranch style home is located on a quiet street and less than a 4 minute walk to Gulf Beach. Ranch style construction means easy access to and from the house with no steps to climb. The newly …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Holiday Perfection!

Left on Aug 19, 2013 for a stay in August 2013

After 10 days in Orlando we wanted to close our vacation with a week by the ocean. Anna Maria Island was recommended and we found Sapphire Surf on the web. The accommodation is in a 2 bedroom bungalow style less than 5 minutes walk from the fabulous beach which faces the Gulf of Mexico. White sands and warm water and safe for kids in the shallows. Sapphire Surf is beautifully furnished, …

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$125

2 BR / 1 BA / Sleeps 6

10 Reviews

$125

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Becker's Beach Bungalow!

2 BR / 1 BA / Sleeps 6 | Quick view
“ Excellent ” 10 Reviews

Details

Reviews

(10)

Charming, newly renovated, the Becker Beach Bungalow offers a comfortable stay less than 2 blocks from the beach. Accommodates 6 people comfortably; master bedroom with 1 queen bed, second bedroom with 2 twin beds, and an additional daybed with pop up in the sun room. The living room also has a queen size sofa bed. …
  • Wireless Internet
  • Housekeeping Optional
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly
  • Wheelchair accessible

Details

Reviews

(10)

Fabulous

Left on Jun 29, 2011 for a stay in June 2011

Becker's Beach Bungalow was a dream come true. So clean, comfortable and containing everything you would need made for a perfect vacation destination. The location is the best...right down the street from the beach, ice cream shop even closer and great restaurants and shops all around. Highly recommend this delightful "rental"...

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$85

2 BR / 2 BA / Sleeps 6

1 / 22

$85

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Villa Nora South

2 BR / 2 BA / Sleeps 6 | Quick view

Details

Only a block to the pristine white sands of our Gulf of Mexico beaches, this lovely two bedroom/two bath duplex is nestled at the end of a long shell driveway, and overlooks picturesque Lake LaVista, a body of water that began its life as a natural lake frequented by the island's early settlers. Sometime in the first…
  • Internet Access
  • A/C or climate control
  • Patio
  • Fitness Room
  • Satellite or cable TV
  • Pet friendly
  • Suitable for children - ask
  • Suitable for the elderly - ask
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