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$223

2 BR / 2 BA / Sleeps 6

TRIPLEPLAY - Anna Maria vacation rentals
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$223

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TRIPLEPLAY

2 BR / 2 BA / Sleeps 6 | Quick view

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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

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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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$274

4 BR / 2 BA / Sleeps 8

6 Reviews

$274

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HAWAIIAN PUNCH

4 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

Beautiful, cheerful and tropucal 4 bedroom/2 bath home with beautiful new furnishings throughout! Comfortable and roomy with split floor plan (two bedrooms on each side!). Ceramic tile throughout, beautiful open kitchen area with breakfast bar and granite countertops. The living room opens up onto a large paver deck …
  • Waterfront
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(6)

Best vacation ever!

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

This was our "family come together" vacation as we live in 4 different locations. We loved our rental house because it offered everything we needed - enough accommodations, pool, fenced in yard, dock access to canal, and absolutely perfect location as to proximity to shops, pier, and beach. It also helped that we had the best weather ever! It seems that every time we talk to any of our kids, …

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$188

3 BR / 2 BA / Sleeps 8

12 Reviews

$188

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Blue Dolphin Inn - Flamingo Up

3 BR / 2 BA / Sleeps 8 | Quick view
“ Excellent ” 12 Reviews

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Reviews

(12)

The Flamingo unit at the Blue Dolphin Inn, located at 780 Jacaranda in the Historic Village of Anna Maria is a wonderful and spacious three 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 …
  • 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

(12)

Megan and Justin's Wedding

Left on Oct 28, 2010 for a stay in October 2010

This was the best vacation ever. I could not have wanted any more. The hammock between two palm trees, the pool, the wooden tower, it was just amazing. I didn't want to leave. Very clean, had everything we needed. Very impressed!

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$608

9 BR / 6 BA / Sleeps 26

5 Reviews

$608

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Blue Dolphin Inn - all units

9 BR / 6 BA / Sleeps 26 | Quick view
“ Excellent ” 5 Reviews

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Reviews

(5)

The Blue Dolphin Inn, located at 780 Jacaranda and 404 Alamanda in the tranquil City of Anna Maria features four units surrounding a tropical heated pool with tiki huts, grills, rooftop observation decks and loads of charm. Each unit has its own private patio and gas grill for an evening of relaxation. Every …
  • 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

(5)

Fun and relaxing family vacation spot

Left on Aug 03, 2012 for a stay in July 2012

First time we have done this kind of vacation and it turned out wonderful! This was a great location for our family get together. Each unit complete with home style living to allow personal space as well as be able to host other family from ajoining units for visits. Our family from ms, SC, IL, and FL enjoyed the space and the private fence that included a pool as well as tiki bar! 2 blocks …

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$290

5 BR / 3 BA / Sleeps 12

6 Reviews

$290

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Gorgeous views,spectacular home!

5 BR / 3 BA / Sleeps 12 | Quick view
“ Excellent ” 6 Reviews

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Reviews

(6)

WELCOME TO ALL DECKED OUT! Whether getting away for a family vacation, with a group of friends, for a wedding or any other occasion, our gorgeous 5 Bedroom home offers everything you could want for a relaxing holiday on Anna Maria Island.... with incredible views of the Bay! Sit by the tropical courtyard garden, …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(6)

A week of Bliss!

Left on Jan 09, 2014 for a stay in May 2013

We were able to spend a week of absolute delight, fun and relaxation. The rooms are large (huge master bedroom). Flat screens in every room, Ipod docking stations everywhere, plenty of everything and large living areas. Yet the best were the views for the decks. The location is perfect. We will definitely return regardless of whether or not 5 bedrooms are needed!

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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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$250

3 BR / 2 BA / Sleeps 10

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$250

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Las Palmas

3 BR / 2 BA / Sleeps 10 | Quick view

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Las Palmas 212 Palm Avenue Anna Maria, Fl. 34216 North-end location just a few minutes walk to Pine Ave and Gulf beaches! This lovely 3 bedroom 2 bath elevated home with private heated pool is situated in the heart of the island, centrally located to everything fun. Comfortable and charming with a Southern-style …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$257

3 BR / 2 BA / Sleeps 8

1 Reviews

$257

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OURPLACEBYTHESEA

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

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Reviews

(1)

Beautiful ground level 3 bedroom/2.5 bath home, with a quiet north end location only a block to the beach! There is a King in the master with a private patio, a Queen in the second, twin beds in the third, and a queen sleeper sofa in the sunroom (which has blinds for privacy), all accommodating up to 8 people. …
  • Shared outdoor pool (unheated)
  • A/C or climate control
  • Parking
  • Grill
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great location, pool

Left on Jul 01, 2014 for a stay in June 2014

We had a great time on Anna Maria with our two college-aged sons. This house is very nicely located, and the pool is wonderful. The home was spacious and comfortable for four people. Our main negative was the beds. All of them were uncomfortable with lousy, flimsy, worn-out mattresses. Also, the kitchen was in some regards well-equipped, but lacking in quality and quantity of pots/pans/…

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$200

3 BR / 3 BA / Sleeps 8

1 Reviews

$200

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Canal Place

3 BR / 3 BA / Sleeps 8 | Quick view
“ Excellent ” 1 Reviews

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Reviews

(1)

Canal Place is a restored three bedroom, three bath Old Florida island home with a pool and hot tub; neutral and relaxing decor with a spacious living room and just a short stroll to the white sand beaches if Anna Maria. Direct waterfront with beautiful canal views. Sleeps upto 8 people. Amenities Include: Full …
  • Waterfront
  • Ocean or water views
  • Hot Tub/Jacuzzi
  • Internet Access
  • Washing Machine
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(1)

Great house for a family beach vacation!

Left on Oct 30, 2013 for a stay in October 2013

We stayed here for a week in October with seven of us and had a great time! The house was incredibly well equipped-the kitchen was stocked with lots of plates, bowls, glasses, pans, etc. which is really helpful when there are seven of us eating together everyday and there are lots of beach towels, beach chairs, and various other beach supplies right there. We used the bikes every day and it was …

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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

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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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$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

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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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$343

4 BR / 3 BA / Sleeps 10

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$343

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LA HACIENDA

4 BR / 3 BA / Sleeps 10 | Quick view

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Located in the heart of Anna Maria, a gorgeous and spacious Mediterranean style 4 Bedroom/3 Bath Home with a Heated Pool in a very private and peaceful setting. Only steps to Pine Avenue shopping and Trolley Stop, 2 blocks to the Beach, and walking distance to the Pier. The open floor plan features granite countertops…
  • 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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$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

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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…
  • Internet Access
  • 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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$209

4 BR / 3 BA / Sleeps 8

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$209

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Pelican Villa

4 BR / 3 BA / Sleeps 8 | Quick view

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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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$214

3 BR / 2 BA / Sleeps 8

2 Reviews

$214

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AMI Retreat: 3BR Pool Home 200 Steps from Beach

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

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Reviews

(2)

Located in the city of Anna Maria on the north end of Anna Maria Island, this gorgeous three-bedroom dog-friendly vacation rental is the perfect place for a vacation retreat! With an estimated 2100 square feet, AMI Retreat has plenty of room to kick off your flip flops and enjoy your down time. With king beds in …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Pet friendly - ask
  • Suitable for children

Details

Reviews

(2)

Relaxing

Left on Feb 14, 2015 for a stay in February 2015

Our rental property was exactly how it was pictured on the web. Plenty of space with all the amenities you need to prepare food in our go out. The newly installed pool and spa made this rental perfect!

The quick access to the beach allowed for many many walks on the white sand beach and plenty of time to enjoy food and cocktails at the sandbar restaurant

I highly recommend this …

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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

Details

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
  • Suitable for the elderly - ask

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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

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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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$214

3 BR / 2 BA / Sleeps 6

1 / 23

$214

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Havana Cay

3 BR / 2 BA / Sleeps 6 | Quick view

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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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$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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$300

5 BR / 4 BA / Sleeps 12

1 Reviews

$300

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Villa Marianne

5 BR / 4 BA / Sleeps 12 | Quick view
“ Excellent ” 1 Reviews

Details

Reviews

(1)

Villa Marianne 111 Maple Ave. Anna Maria, Fl. 34216 Wow, you just can't say enough great things about this beautiful beach villa! This 5 bedroom, 4 bathroom home so close to the beach- no more than a 1 minute stroll and located on the prestigious North end of the island. Every room is exquisite- decorated to …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

Details

Reviews

(1)

Awesome place to stay!!

Left on Mar 22, 2015 for a stay in March 2015

We just returned from our week long stay at Villa Marianne and couldn't be happier. We were two families- mine and my cousin and hers. 4 adults total, and 5 kids ages 8,6, 4,3, and 1. First of all, you are just a short walk to a lovely stretch of beach. At the end of the street there is a short path. And since it isn't a public access area, there aren't that many people- even during crowded …

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$330

5 BR / 3 BA / Sleeps 14

1 / 24

$330

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Villa Del Sol

5 BR / 3 BA / Sleeps 14 | Quick view

Details

Villa Del Sol 211 Chilson Avenue Anna Maria, FL 34217 This is an exquisite, newly remodeled 5 bedroom, 3 bath ground level home with available boat dock. Inside the home you will find quality furnishings with a Caribbean decor. The open floor plan provides the perfect space for spending time together or …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$343

4 BR / 4 BA / Sleeps 11

2 Reviews

$343

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HAV'ANNA HIDEAWAY

4 BR / 4 BA / Sleeps 11 | Quick view
“ Excellent ” 2 Reviews

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Reviews

(2)

When you 'have anna maria' on your mind, you'll want 'hav'anna hideaway' for your vacation home. This newly constructed 4 bedroom, 4 bath home is located just one short block to the beautiful and sparkling gulf beach. The main floor of the home consists of an open concept living room, kitchen with breakfast bar …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Fantastic Family vacation

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

We rented Hava'nna Hideaway in June 2013. It was the first family vacation for all ten of us. The house was very clean and roomy so we didn't feel hemmed in. We cooked most of our meals and used the BBQ grill outside a lot. It's about a block from the beach but they provide a beach wagon to haul your stuff. We loved the small pool outside and we used it a lot just sitting around talking and …

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$236

3 BR / 2 BA / Sleeps 8

1 / 18

$236

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BEACHCOMBERS

3 BR / 2 BA / Sleeps 8 | Quick view

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Beachcombers is a spacious 3 bedroom/2 bath home with all of the "Old Florida Charm" you could ask for. Situated on Spring Avenue, just a couple of blocks to the Gulf of Mexico on Anna Maria's beautiful north end! Easy walking distance to many shops, restaurants, the Anna Maria City Pier and a short block to the free …
  • 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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$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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$175

2 BR / 2 BA / Sleeps 4

1 / 15

$175

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Windsong Cottage

2 BR / 2 BA / Sleeps 4 | Quick view

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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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$171

3 BR / 2 BA / Sleeps 6

5 Reviews

$171

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Coastal Cottage: 3BR Pet-Friendly Pool Home

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 5 Reviews

Details

Reviews

(5)

The adorable Coastal Cottage, located in the laid-back city of Anna Maria, is the perfect place to take a totally carefree vacation. The white sand beach of Anna Maria Island and the azure blue waters of the Gulf of Mexico are only a short stroll from this delightful three-bedroom, two-bath vacation rental. An open …
  • Wireless Internet
  • Washing Machine
  • Clothes Dryer
  • A/C or climate control
  • Patio
  • Suitable for children - over five
  • Suitable for the elderly

Details

Reviews

(5)

Coastal Cottage

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

We loved the location. We enjoyed the house, but we did not know it was up for sale until we pulled in the driveway. We had too many requests for viewing which disturbed our visit enough that we decided not to book with you again next year.

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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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$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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$223

2 BR / 2 BA / Sleeps 6

4 Reviews

$223

Inquire

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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$250

4 BR / 4 BA / Sleeps 10

1 / 25

$250

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Island Dream

4 BR / 4 BA / Sleeps 10 | Quick view

Details

Island Dream 157 Crescent Drive Anna Maria, FL 34216 An exceptional property with glorious views of the Sunshine Skyway Bridge from its entrance, this beautiful, newly built and elegantly furnished four bedroom and four bathroom home on the desirable north end of Anna Maria is situated in a quiet residential …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$317

4 BR / 3 BA / Sleeps 9

2 Reviews

$317

Inquire

TOES IN THE WATER

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

Details

Reviews

(2)

Newly remodeled, 4 bedroom/3 bath home, just 90 Steps to the beach, with a large private HEATED pool! Quiet setting in the beautiful north end of Anna Maria, and located west of Gulf Drive for easy beach access with no streets to cross. Easy walking distance to many shops and restaurants, and less than a block to …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Great location, adorable and clean!

Left on Oct 27, 2013 for a stay in January 2013

My parent rented this house when they came to visit last winter. We stayed for a week in late January(?) to early Feb and my 3 year old son still asks to go back.

Personally I think that speaks volumes as 1. He is young 2. We have stayed/visited some amazing places since then. He doesn't ask to go to Disney World, he wants to go to 'his' beach house.

It may look small from the front, but it …

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$143

3 BR / 2 BA / Sleeps 6

1 / 18

$143

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Bay Bungalow

3 BR / 2 BA / Sleeps 6 | Quick view

Details

Bay Bungalow 607 N. Bay Blvd. Anna Maria, Fl. 34216 Brand new heated pool! Bay Bungalow is a newly updated elevated bungalow located on the North end of the island, just across from the famous Rod and Reel Pier and only 2 blocks from Bean Point beach. The custom decoration includes nautical themes and artwork …
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

3 BR / 3 BA / Sleeps 8

1 / 26

$300

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Heron House

3 BR / 3 BA / Sleeps 8 | Quick view

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Heron House 213 Elm Ave. Anna Maria, Fl. 34216 Wow, this luxury 3/3 North-end elevated home has it all! Just newly remodeled and ready to go! Just a short walk to it all- the beautiful Gulf beach, the fun and entertainment of Pine Ave. and even walk to the fantastic Sandbar restaurant. The home has approx. 2700 …
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$309

4 BR / 3 BA / Sleeps 8

2 Reviews

$309

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NORTH END CHIC

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

Details

Reviews

(2)

Beautiful, Brand New, Ground Level 4 bedroom/3 bath home, just around the corner from the Rod & Reel Pier, Bayfront Park, and just a couple of blocks to Fabulous Bean Point Beaches and Sunsets. Beautiful back yard with Heated Pool surrounded by a large paver deck and beautiful outdoor lounging area by pool. Open …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Slice of heaven

Left on Oct 06, 2013 for a stay in October 2013

This was our sixth visit to anna Maria Island and by far the best because of the house. It was wonderful in every way possible, immaculate, beautifully decorated, comfortable beds and quiet. Ami accommodations are easy to work with and very quick to answer my questions prior to arriving and when we checked in. We went to the Rod and Reel for supper one night which as always was excellent and went…

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$240

3 BR / 2 BA / Sleeps 6

2 Reviews

$240

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ANNA BANANA

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

Details

Reviews

(2)

Great Ground Level 3 Bedroom/2 Bath Home with a Heated Pool located in the quiet north end and just 3 houses to the beach!! King-Sized master bedroom with TV, Queen in the 2nd Bedroom with TV, and Twins in the Third with TV. Cable TV, DVD, and Flat Screen TV in Living Room. High speed Internet, Washer/Dryer, AC, Gas …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

clean, cozy, and close to everything we need!

Left on Aug 22, 2013 for a stay in July 2013

Anna Banana house was pristinely clean, well-decorated, cozy, had plenty of room for the 4 of us, and was the most convenient place we have ever stayed on anna Maria Island. It is close to a lovely stretch of beach where we found fewer people and lots of relaxation...not to mention sand dollars, and lovely shells of all sorts. It is convenient to the trolley stops on Pine, and located on a …

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$253

3 BR / 2 BA / Sleeps 8

1 / 33

$253

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HURRICANE HOUSE

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Beautifully redone 3 bedroom/2.5 bath home! Ceramic tile throughout, and brand new open kitchen area with breakfast bar. Beautiful large caged pool area with huge covered patio! Only a block to the beach, the Sandbar Restaurant, Ginny and Jane E's, Rudy's Subs, Feeling Swell and more. Just a few steps away from …
  • 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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$100

2 BR / 2 BA / Sleeps 8

1 / 13

$100

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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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$200

3 BR / 2 BA / Sleeps 6

1 / 12

$200

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A Snails Place

3 BR / 2 BA / Sleeps 6 | Quick view

Details

A Snails Place 302 Spring Avenue Anna Maria, Fl. 34216 This beautifully decorated 3 bedroom, 2 bath ground level home is just a short walk to the Gulf of Mexico. With it's convenient location on Spring Avenue you are walking distance to historic Pine Avenue! This adorable cottage offers a splash pool (not heated…
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$209

4 BR / 3 BA / Sleeps 8

1 / 19

$209

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Casa Muratti

4 BR / 3 BA / Sleeps 8 | Quick view

Details

Casa Muratti 210 Palmetto Avenue Anna Maria Fl. 34216 This is an exceptional 4 bedroom 3.5 bath Mediterranean style home just a short walk to the Gulf of Mexico. With its modern decor and bright open floor plan this home is perfect for your vacation getaway! There is a private heated pool and a large covered patio …
  • Outdoor Pool
  • Internet Access
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$283

3 BR / 2 BA / Sleeps 6

2 Reviews

$283

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CARIBBEAN SOUL

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

Details

Reviews

(2)

Beautifully remodeled 3 bedroom/2.5 bath home with luxury amenities on the North End of Anna Maria, just 4 houses to Bean Point, one of the quietest beaches on the island, and 2 blocks to the famous Rod & Reel Pier! Private Backyard with Heated Pool, and an open floor plan with vaulted ceilings! Sleeps up to 6. …
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • A/C or climate control
  • Suitable for children
  • Suitable for the elderly

Details

Reviews

(2)

Fabulous getaway

Left on Sep 28, 2013 for a stay in April 2013

This was my first trip to anna Marie Island. The area and weather is gorgeous in april. The accommodations are amazing with everything you can possible want or need provided. I would love to make this an annual event.

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$141

2 BR / 1 BA / Sleeps 5

1 / 30

$141

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YELLOWBIRD COTTAGE A

2 BR / 1 BA / Sleeps 5 | Quick view

Details

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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$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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$141

2 BR / 1 BA / Sleeps 5

1 Reviews

$141

Inquire

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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$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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$209

4 BR / 3 BA / Sleeps 10

1 / 17

$209

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Sundown North

4 BR / 3 BA / Sleeps 10 | Quick view

Details

Sundown North 300 N. Shore Dr. - Unit B Anna Maria, Fl. 34216 Sundown North- a unique water front property that has 4 bedrooms, 3 bathrooms and a private heated pool one block to Pine Ave. It sleeps up to 8 guests in beds and 10 total. Sundown North also has a separate living room upstairs with large TV and …
  • Private Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$250

5 BR / 3 BA / Sleeps 12

1 / 22

$250

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Tortuga Bay

5 BR / 3 BA / Sleeps 12 | Quick view

Details

Tortuga Bay 9405 Gulf Dr. Anna Maria, FL 34216 This one is extraordinary! Tortuga Bay is a completely renovated, ground level, 5 bedroom property that has one of the most outstanding tropical pools on the island- featuring a theme-park style water-slide! Located in the prestigious city of Anna Maria, it is the…
  • Heated Pool
  • High Speed Internet
  • Patio
  • Television
  • DVD Player
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$300

5 BR / 3 BA / Sleeps 10

1 / 26

$300

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Whitecaps

5 BR / 3 BA / Sleeps 10 | Quick view

Details

Whitecaps 749 Jacaranda Anna Maria, FL 34217 Whitecaps is a luxury tropical island style 5 bedroom, 3.5 bathroom home located at the prestigous north end of Anna Maria Island. This home sits only 1 block in from the Gulf beaches and is only about a 1 minute stroll over to the water. It has wonderful views of…
  • Outdoor Pool
  • Dishwasher
  • Suitable for children - ask
  • Suitable for the elderly - ask

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$244

3 BR / 2 BA / Sleeps 8

1 / 30

$244

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HAV'ANNA DAYDREAMIN

3 BR / 2 BA / Sleeps 8 | Quick view

Details

Completely Remodeled 3 bedroom/2 bath home with private Heated pool. Beautiful new tile, Granite countertops, all new appliances, and living room overlooking the heated pool. Bright, open kitchen, dining and living area! Sleeps up to 8. 1500 Sq. ft. 204 Archer Way, Anna Maria 3 Bedroom/2Bath Home with Heated Pool…
  • 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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$235

3 BR / 2 BA / Sleeps 6

12 Reviews

$235

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Ocean View 3 bedroom, pool, North Shore Drive

3 BR / 2 BA / Sleeps 6 | Quick view
“ Excellent ” 12 Reviews

Details

Reviews

(12)

Just steps to the sugar sand beaches in Anna Maria, FL. Your 3 bedroom, 2 bath, pool home with sweeping gulf views from two elevated front porches is located in the charming northern end of Anna Maria on North Shore Drive. If you are looking for a tropical vacation home to just relax, take long restfull naps, and …
  • Ocean or water views
  • Internet Access
  • Washing Machine
  • Clothes Dryer
  • Outdoor Dining Area
  • Pet friendly
  • Smoking allowed - ask
  • Suitable for children
  • Suitable for the elderly - ask

Details

Reviews

(12)

Perfect!

Left on Jul 18, 2012 for a stay in July 2012

This home is lovely, just as the pictures show. It is directly across the street (with beach access) from the most beautiful beach on anna Maria with gorgeous views from the balconies. Everything you need is right here including beach chairs, beach towels, beach umbrella, and even floaties. The pool is on the small side but it is perfect for a quick cool down with lots of poolside lounge …

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