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Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly

Photo gallery for Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly

Exterior
Exterior
Pool
Exterior
Exterior

Reviews

9.4 out of 10
Exceptional
2 bedrooms2 bathroomsSleeps 4800 sq ft

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Air conditioning
  • Outdoor Space

Rooms & beds

2 bedrooms (sleeps 4)

Bedroom 1

1 King Bed

Bedroom 2

1 Queen Bed

2 bathrooms

Bathroom 1

Toilet · Shower only

Bathroom 2

Toilet · Shower only

Spaces

Deck or patio
Kitchen
Dining area

About this property

Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly

The cozy front porch of Gulf Winds A invites you to have your morning coffee or your evening cocktail and in the back yard you can enjoy your dinner and make use of the gas grill. A huge table umbrella provides you with shade if needed. The two bedroom two bath unit is located on a very quiet street. The Master bedroom has a king size bed and the guest bedroom has a queen. The home has been totally remodeled, everything is new from furniture to floors and appliances. There are TV's in the master bedroom and the living room, and of course there is free WiFi. Everything you need to enjoy your visit is provided: dishes, cookware, linens, towels, beach chairs and beach towels, etc.
Gulf Winds is a short walk away from the white sandy beaches of the Gulf of Mexico. Just take the short-cut through North Beach Village to get to the beach. The Holmes Beach Dog Park is another short walk down the street across Marina Drive. The bus stop of the free Island Trolley is close by as well as restaurants, shops and bars. Do not miss this GEM. For bigger parties you may also book Gulf Winds B.
Dogs up to 25lb are welcome. Pet fee is $200 per pet plus taxes, maximum of 2 pets unless otherwise approved by FDR.

Accommodates up to 4 people. Minimum Stay Required: 1 Week.
Max. parking: 2; VRC #18-000021

You are vacationing in a residential area. Please be a good neighbor by keeping the noise to a respectful level during the day and night. Excessive and unreasonable noise can deprive neighbors of the peaceful enjoyment of their private property.

* Cancellation more than 90 days prior to arrival will receive a deposit refund less a $250 cancellation fee. Cancellation less than 90 days prior to arrival will forfeit all deposit received. Cancellation less than 60 days prior to arrival will forfeit all monies on account. Cancellations must be confirmed in writing.
Our prices include all fees. No hidden fees.

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House Rules

Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
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Children

Children allowed: ages 0-17
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Events

No events allowed
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Pets

Pets allowed
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Smoking

Smoking is not permitted

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card, or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
Onsite parties or group events are strictly prohibited
Host has not indicated whether there is a carbon monoxide detector on the property; consider bringing a portable detector with you on the trip
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher

About the neighborhood

Holmes Beach

Located in Holmes Beach, this vacation home is near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Discover the area's water adventures with scuba diving and snorkeling nearby, or enjoy the great outdoors with cycling and hiking/biking trails.
View more Vacation Homes in Holmes BeachOpens in a new window
Map
Holmes Beach, FL

What's nearby

  • Bradenton Beach - 6 min walk - 0.6 km
  • Island Gallery West - 8 min walk - 0.7 km
  • Holmes Beach Beaches - 14 min walk - 1.2 km
  • Manatee Public Beach - 2 min drive - 1.8 km
  • AMI Paddleboard Adventures - 3 min drive - 2.1 km

Getting around

  • Sarasota-Bradenton Intl. Airport (SRQ) - 45 min drive

Restaurants

  • ‪The Ugly Grouper - ‬6 min walk
  • ‪Anna Maria Island Beach Cafe - ‬4 min drive
  • ‪The Sandbar Restaurant - ‬5 min drive
  • ‪Anchor Inn - ‬5 min drive
  • ‪Ginny's & Jane E's - ‬4 min drive

Frequently asked questions

Is Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly pet-friendly?

Yes, pets are allowed at this property.

How much does it cost to stay at Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly?

As of Mar 23, 2026, prices found for a 1-night stay for 2 adults at Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly on May 28, 2026 start from $211, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking?

Onsite parking is available at the property.

What time is check-in at Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly?

Check-in begins at 4:00 PM.

What time is check-out at Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly?

Check-out is at 10:00 AM.

Where is Cozy cottage on Anna Maria Island, 2 bedroom - pet friendly located?

Situated by the sea, this vacation home is within a 10-minute walk of Bradenton Beach and Island Gallery West. Holmes Beach Beaches and Palmetto Avenue Beach are also within 1 mi (2 km).

Reviews

9.4

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labeled.
Learn moreOpens in a new window
Rating 10 - Excellent. 22 out of 28 reviews
Rating 8 - Good. 5 out of 28 reviews
Rating 6 - Okay. 0 out of 28 reviews
Rating 4 - Poor. 0 out of 28 reviews
Rating 2 - Terrible. 1 out of 28 reviews

10/10

Cleanliness

10/10

Check-in

9.4/10

Communication

9.8/10

Location

9.8/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Jennifer D.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Fantastic cottage!

Totally enjoyed our stay! The cottage is adorable and well stocked for anything you could possibly need. Walking distance to the beach. It’s heaven!
Stayed 8 nights in Jul 2021
Verified

10/10 Excellent

Don R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Place

Beach decor and beautiful property near the beaches and restaurants. No need to fight the travel to and from the island when you’re already there. Will definitely come back.
Stayed 30 nights in May 2021
Verified

10/10 Excellent

Gene B.

Liked: Cleanliness, check-in, communication, location, listing accuracy

AMI

Nice house, just what was needed. Close to beach.
Stayed 7 nights in Jun 2024
From a partner site

10/10 Excellent

Jason N.

Cute cottage

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: The cottage was in a great location, close to the beaches and restaurants. The place was clean and beds very nice.
Verified

10/10 Excellent

Bill F.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Sunny all month

What a gem. Very well located to Holmes Beach restaurants and shops.Easy walking to each and dog parks.
Stayed 28 nights in Jan 2023
From a partner site

10/10 Excellent

Patricia S.

January Getaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location with a short walk to the beach. Nicely furnished and very clean. Front porch to relax while reading and a large backyard patio. 2nd stay and this location and very pleased with all it has to offer.
Verified

8/10 Good

Keith W.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Good Location, Comfy Cottage

The cottage was well located in Holmes Beach, and an easy walk/bus ride to either end of the island. It was spacious with a cozy feel, and the beds were surprisingly comfortable. The only reason I gave it 4-stars was because the A/C was not working and the water heater was unreliable on Day-1. The A/C was fixed in 2 days, but the water heater had to be replaced after several days. To be fair, both FDR and the owner were very responsive.
Stayed 14 nights in Mar 2025
From a partner site

10/10 Excellent

A guest from Overland Park, KS L.

Overall a very good experience.

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was more than happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Oh what an improvement two comfortable chairs would be. Hideaway couches are notorious for being uncomfortable, but two other chairs would really help.need some kind of vacuum to pick up sand.
From a partner site

8/10 Good

Alejandro V.

Relaxing place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: With my family enjoyed this beautiful place, close to the beach. If this house has a pool will be gorgeous!!!
Stayed 7 nights in Jul 2022
From a partner site

10/10 Excellent

Gwendolyn P.

Definition of rest and relaxation

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We had a wonderful time at this property. It was not only charming and cozy; but, it was also immaculately clean. It was so welcoming and had really all the amenities that had been detailed in the description.We spent a lot of time on the front porch. It was so nice and allowed for a lot of good family connection time - unplugged.The street is not a direct route between Gulf and Marina; so, the road is quiet - which is really nice as well.Lastly, it is a highly walkable location around the island.
From a partner site

10/10 Excellent

Patricia S.

January Getaway

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Great location. Nicely decorated and very clean. Front porch a perfect location for afternoon reading.Very short walk to the beach for a morning walk and to see the sunset.
Verified

10/10 Excellent

Betty R.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Wonderful Stay

We had a lovely stay of 9 days. The house was perfect for my aging mother because it easy one story and was easy for her to maneuver around. I wish there was a bar in the shower for her but we managed. We had an issue with air conditioning but it was resolved within hours and it was a Friday evening!! I love that maintenance is on the island and was so friendly and polite. Neighborhood was quiet. We really loved the patio and we used the grill alot! I will definitely be back!!
Stayed 9 nights in Jul 2021
From a partner site

8/10 Good

A guest from Chantilly, VA

Small but decent place

Rating Details: The property manager was more than helpful. The vacation rental was very clean. I was more than happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: PROS: * they have beach towels, styrofoam cooler, pails for kids and a beach "stroller" which helps with the 0.3-mile walk to the actual sand of the beach* the outdoor back area is well equipped with a Weber grill and 6-person commercial-grade umbrella* front porch has a small settee, 2 chairs and small coffee table and end "stands" - although the awning leaks a bit, there is a 3 foot overhand from the house so you can push up against the wall to sit out when it is raining* it's 0.3 miles to the Ugly Grouper and the Salty Dolphin boat rides, 0.5 to the "town" of Holmes beach and 1.25 to Manatee beach which we consider walkable although there is a free trolley that stops about 0.25 * 2 ensuites is nice although the laundry/utility room is through the largest bedroom as well as the fastest access to the back yard* the management staff was extremely responsive to 2 issues we had although the website message center did not have a contact form (maybe it was the browser I was using?) CONS:* no outdoor hose* only one towel rack in the front bedroom so squeezing 2 bath towels and a hand towel had them falling to the floor a lot - would be good to get a hook at least to the right of the sink and maybe behind door* you'll need to drag a chair over to the utility room if you want to see the dryer settings and you're not 6 feet 2 inches tall* too many decorative pillows which took up a lot of valuable closet space* the areas around the door handles were dirty (very apparent with white doors) but I left comments on the form so maybe they will remedy that* kitchen is extremely tiny and no dishwasher but the did provide dishsoap and a clean sponge* we're not fans of blended drinks, but if you are, we did not see a blender so you may want to check* conflicting information in the binder so best to call the office if you have questions
From a partner site

10/10 Excellent

Jesica R.

Gulf Winds Stay

Rating Details: The property manager was very helpful. The vacation rental was very clean. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Property was perfect for our needs during our 10 day stay. Duplex that’s newly renovated, with everything you need and was clean. With the property being well appointed, I’d recommend a couplethings to better outfit the property: towels were only a few and hodge podge mixture of low quality. Seemed like someone went to a thrift store and grabbed a few wash clothes, hand towels and body towels. There were 2 towels for the master bath, 2 towels for the 2nd bedroom bathroom. When you’re out at the beach and sweating all day in the heat, it’d be nice to have a couple more towels so you aren’t having to do laundry frequently just to shower. Living room chair is wicker and uncomfortable to sit in. Recommend owner invest in something suitable for their property. Couch is nice and comfortable- a nice comfortable chair that you’re able to sit in would be enjoyable and realistic assuming you have up to 3 or 4 people in this property. Couch is too small to squeeze 3 people on it.Tile floor is beautiful but our feet was black when walking around on it. Cleaning it beyond brooms and vacuum would be nice.
Verified

10/10 Excellent

Robin M.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Cute Duplex near everything!

Had a great vacation here while needing to get away visiting family! The home was clean, decorated nicely and everything worked well. We would stay again.
Stayed 10 nights in Apr 2021
From a partner site

8/10 Good

A guest from Farmington, UT K.

Small but nice

Rating Details: The vacation rental was very clean. I was very happy with the location. I was more than satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Overall lived up to expectations. Living space very tight for two adults and one small child. Beach, park, and restaurants all within walking distance.
From a partner site

10/10 Excellent

Kathleen K.

Quarantine in paradise

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This cute place was a perfect get away for my small family. Quietly located near shops and beach. Would definitely stay here again!
Stayed 7 nights in Jul 2020
Verified

8/10 Good

Farah C.

Liked: Cleanliness, check-in, location, listing accuracy

Tiny, spotless, nice location

Very clean Nicely updated Good location Very comfortable Has all necessities you would need for 2-4 people No dishwasher No outside water (to rinse sand before coming in)
Stayed 11 nights in Jun 2020
Verified

10/10 Excellent

J J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Great place for a relaxing vacation.

The place was great for us (two couples). A very nice backyard patio. Beds were very comfortable. Holmes Beach was nice place to relax. Enjoyed the grill. Will come back.
Stayed 7 nights in Mar 2020
From a partner site

10/10 Excellent

J J.

Liked: Cleanliness, check-in, communication, location, listing accuracy

Nice Get-Away

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: We really enjoyed our trip. Did a few day trips (one north and one south) and loved the place we stayed.
Stayed 7 nights in Mar 2020
From a partner site

10/10 Excellent

Steve K.

Lovely, well furnished, conveniently located vacation cottage

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: While the cottage is cozy, it is very comfortable. Location very close / walking distance to restaurants and beaches in Holmes Beach. Quiet and peaceful neighborhood. Beautifully finished backyard is a bonus in warmer weather.
Stayed 28 nights in Dec 2019
From a partner site

10/10 Excellent

Kim B.

Gulf Winds Wonderful!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Lovely home! Inside and out! Easy walk to the beach!! Nice neighborhood!
From a partner site

10/10 Excellent

Gwen M.

Wonderful place to stay

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: I stayed at Gulf Winds for 6 months and it is a great property located in the heart of Holmes Beach. I was able to walk almost everywhere I wanted to go...stores, restaurants, the beach, and even the dentist when I broke a tooth! The owners are very friendly and promptly took care of any minor concerns I had. I can't wait to get back!
From a partner site

10/10 Excellent

Super zufrieden mit unserem Haus Gulf Winds

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: Wir haben zum sechsten Mal ein Haus bei Florida Dreams gemietet und waren auch diesmal begeistert. Als wir ankamen erwartete uns ein wunderschönes, sauberes und sehr gepflegtes Haus. Alles wie versprochen. Kurzer Fussweg zum tollen Strand und zu netten Restaurants. Danke Florida Dreams, wir kommen wieder.
From a partner site

10/10 Excellent

Brenda B.

The cutest cottage!!!

Rating Details: The property manager was very helpful. The vacation rental was spotless. I was very happy with the location. I was very satisfied with the condition of the vacation rental. Overall, I recommend this vacation rental. Reviewer Comments: This was a completely updated cottage, the pictures are spot on! The house was very clean and spacious, and although we did not cook, it appeared all the cookware was available to do so. The backyard was adorable with a huge deck and BBQ. The front has a beach landscape, which was unique. My college aged daughter and I stayed here to attend a wedding at a near by B&B. This was a very safe and quiet neighborhood. It's probably a 5-8 minute walk to a public beach from here, but the unit had a nice wagon to pull your chairs and cooler. The Realty company was very responsive from my very first call, and answered my many questions. They were very easy to work with. Just read the conditions and check out procedures and you'll be fine! We are from the PNW and this was our first trip to AMI, but I am already planning on a return trip! I am happy to recommend Florida Dreams Realty of AMI and this particular rental unit!

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