Starting at $200.00 a night
2500 sqft
Please refer to bottom of description for more information concerning stays with a pet.

Step into this fantastic pet friendly Anna Maria Island vacation home, only two blocks to turquoise waters of the Gulf of Mexico and one block to the bay!

This house is pet friendly with the huge front porch completely secure and a completely fenced in back yard as well.

This five bedroom, three bathroom large home is a memory maker for sure! Sleep the entire family, a few couples, or a group of friends for the perfect beach get-away!

There is a plethora of outdoor living space, plenty of room for everyone to spread out. There is a huge front porch with a table to dine, play cards, or just enjoy the bay breeze as it finds it way through the peaceful palms in the front yard. There is a balcony off the master bedroom (we highly suggest (weather permitting) having those doors wide open! And if you get a chance, grab a cup of coffee and make it back to the porch for sunrise! The back balcony joins the two back bedrooms. Curl up with a book, gaze at the stars, the perfect place to unwind before bedtime.

The back patio is a completely private tropical oasis! Mature Florida landscaping and a fence creates a barrier from neighbors and makes this back yard perfect for your four legged visitors as well! 

The kitchen is fully equipped with anything you would possibly need to prepare meals while on on vacation! Not lacking seating room, the kitchen table seats 6 and there are 2 stools at the breakfast bar for additional seating.

Enjoy soft buttery leather furniture in the living room, perfect for a snooze or to cuddle up and watch a movie!

There are FIVE bedrooms with the following sleeping arrangements:

Upstairs Master: King bed, master bathroom with walk in shower

Upstairs Guest Room 1 - Two twin beds (one trundle for special sleep overs!)

Upstairs Guest Room 2 - Daybed with trundle (sleeps 2)

Upstairs Bathroom - Tub / shower

Downstairs Guest Room 3 - Queen bedroom

Downstairs Guest Room 4 - Bunk Beds (both are full size!)

Downstairs Bathroom - Tub / Shower

There are plenty of linens, towels, and other fun beach accessories that past guests have left!

We hope you choose to start your family / friend traditions at the Pirates Nest! It's a lovely home on a beautiful island, it's everything you've been dreaming of!

Maximum Parking: 4 vehicles

A pet fee of $100 + tax will be applied after reservation has been made. No animals other than (2) two dogs allowed. Please check with us prior to booking for dog approval. No pets allowed on beds & furniture.
King Size
Queen Size
Single/Twin Size
Single/Twin Size
Single/Twin Size
Single/Twin Size
Single/Twin Size
Single/Twin Size



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3 - 7 Night Minimum

30% Down Payment at time of reservation. Balance due 30 days prior to arrival.

Fee Amount
Damage Waiver $50.00
Taxes 12%
Booking Fee $65.00
Cleaning Fee $250.00

Bradenton Beach , FL , United States


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Beach vacation on Anna Maria Island

Date of Stay:

My friends and I enjoyed this house. It's cozy and cottagy but ample enough to accommodate two families. The house provides all of the necessities you could think of, and the welcome "goodies" bag was a bonus. The house was clean and well kept. I loved the patio rocking chairs in the front porch that did not seem to be rocking chairs at first sight! Some suggestions would be to have a couple more chairs for the dining table and better quality bath towels. The upstairs A/C unit cooled the rooms unevenly. Overall, we had a comfortable and great experience. Date of arrival - August 8, 2021

A bit old but nice

Date of Stay:

We loved our stay. The house is comfortable. The master bedroom is lovely with the sunrise every morning. Some appliances are a bit dated, but functional. Nice quiet neighborhood. Date of arrival - July 17, 2021

Beach Bums from Pittsburgh to Anna Maria

Date of Stay:

Location is everything when we plan our beach vacation. This house was only 2 blocks from the beach access which we loved. It is on a narrow area of the island (with many residential houses) so the beach was not crowded. We fly from to Florida not drive…So if you don’t drive down or have a rental car this is how we got around. We had a car service called ALD Limos from Sarasota airport take us to our beach house. It’s only a 5 minute walk to the trolley stop from the beach house. We rented a golf cart that seated 4 and we had 8 in our party so we used the trolley and the golf cart. I recommend reserving a golf cart at least 2 months in advance because they get booked up quickly. At least the less expensive ones do. Our golf cart was 750 for the week (bc we waiting to book) and other places rented there’s for 350 for the week. Just a heads up to save some $$. The Publix grocery store was 0.6 miles from us. Beautiful beach~~amazing sunset~~warm water~~got to see manatees swim by along with dolphins on a separate day. We honestly don’t care about the beach house amenities. As long as there are enough bedrooms and baths we are happy!! So if your looking for an updated beach house this may not be for you. The place was very clean and had everything we needed for our vacation. Bean Point was also a beautiful place to head to with your morning coffee to look for shells and just take in the gorgeous sunrise. We love Anna Maria Island and will definitely visit again! I tried to include things in my review about the location and transportation that others left out because I had to read through endless reviews for tidbits of info that I was looking for.

Super Home

Date of Stay:

We loved house, my kids enjoyed the poo table and the swimming pool. We enjoyed the house as it had tv's in every room. If we ever go back to Florida we would get the same house. I would rate it as a 10. Thanks so much. Date of arrival - May 31, 2021

Great house great location

Date of Stay:

Our stay was wonderful. House is plenty big for large parties. It is clean and well taken care of. Perfect location for beach and restaurants/shops. Would definitely stay here again. Published Apr 25, 2021

Stayed the month of March

Date of Stay:

First of all the property manager Alex is wonderful and super prompt in taking care of the couple issues I had! Would not hesitate one bit to rent a property he manages. The house itself could be a complete gem if the owner would give it just a little TLC. Outdoor furniture needs replaced (nothing expensive just new) I understand the salt air and weather is tough on it! I would definitely add a kuerig to the kitchen inexpensive and a nice little touch! The location itself is perfect, great areas to walk your fur babies. The neighbors are friendly and the area is very safe to walk about. *** Just an FYI to those that would be bringing their dogs, the porches are perfect for them to enjoy the weather, the fenced backyard area does not have any grass it is all crushed shells (which is pretty typical in Florida) my dog just was not a fan so we walked a lot (good for me). So bring lots of doggie bags and keep the area beautiful! I would rent this property again Published Apr 18, 2021

PERFECT LOCATION—nice beach house with plenty of space and great layout! Great rental value!

Date of Stay:

The perfect beach sanctuary, home away from home hidden gem PERFECT LOCATION! Great space and floor plan. Pretty much has everything you need for a relaxing day at the beach or chill at home under your choice of paradise landscaping on the front porch, balcony with water view or back patio. Some of the appliances-bathroom are dated but everything was pretty clean considering. The process as super simple and communication was excellent. Note to owners, NO NEED for crazy kitchen or batch room upgrades. You have a little gem. Just needs a little love in just a few places and it’ll be perfect! Published Mar 16, 2021

Great family stay

Date of Stay:

We enjoyed our stay at the Pirates Nest for Thanksgiving 2020. It was a family trip so the house was full and we used just about every inch, lol!. We loved the location, just a short walk to the beach or the park by the bay. Also loved the front porches where we spent the majority of our outdoor time when we weren't at the beach or the park. The property is older so if you are looking for the most up to date amenities, you won't find them here but if good family time is your goal than this place would fit the bill. We would stay again! Published Dec 14, 2020

Great house with lots of space

Date of Stay:

We enjoyed our stay immensely. The house is big and allowed us to spread out when needed. Even though you can’t see the beach from the house, there is a beautiful view of the bay from the upstairs master bedroom to watch the sun rise. There is also a brand new washing machine for all of those beach towels that are provided. The house is walking distance to many great restaurants! This was our first time to Anna Maria Island and we were impressed.

Family get together at the Pirates Nest.

Date of Stay:

Rental process was easy and efficient. The property manager was quick to respond and accommodating. I feel the property itself could use some TLC and deep cleaning and a few more features to make it more accommodating; especially for our 2 week stay.

Perfect Beach House

Date of Stay:

We had a great time. There was 8 of us with 5 kids and the house was perfect. It had room for everyone to sleep and its location was perfect for easy beach access.

Location could have been better.

Date of Stay:

Nice house with plenty of accommodations.

Great Beach House!

Date of Stay:

This is a great beach house just a short walk away from the beach. Home is comfortable and sleeps more than I can count. Has multiple decks. Quiet neighborhood. Perfect beach home!


Date of Stay:

What a cute place. We all had a blast. Definitely want to go back!

Family time

Date of Stay:

This property was walking distance to the beach and a park it was amazing, definitely will stay again.

Great deal for a full family vacation.

Date of Stay:

You can't beat the location if you're looking for Sunrise and Sunset viewing. The property is pretty dated, but I'm used to that and not looking to pretend I'm a millionaire. If you're going for the beach and to enjoy the island while spending quality time with family and friends, this is perfect.

June 2019

Date of Stay:

On the upside, the location of the property was great, with the promised two minute walk to the beach leading to a beautiful and uncrowded stretch of the coast. The customer service by the property manager was fantastic, and the place was well cleaned. On the downside the wi-fi was mostly non-existent, and the furniture and appliances had all seen better days (especially the outdoor furniture). It's way past time for the owner to replace furniture and fix that sagging front deck if they ever expect a five-star rating. I'll use the management company again for my June 2020 stay on Anna Maria Island, but I'll pass on staying at the Pirate's Nest with so many better maintained properties on the island. Owner's Response: Thank you for the feedback. We recently added a Wifi extender to the second floor to provide better Wifi coverage, but when a device is connected to the extender it appears to cause more problems at times than it actually helps. We will look into re-positioning the router to a more central spot in the home for better connectivity. The furnishing in the pictures remains accurate, more dining room chairs have since been added and we are glad to say that our Pirates seems to fit a great number of our past guests, with many wanting returning.

Fantastic Family Fun Spot

Date of Stay:

The Pirate’s Nest was the perfect spot for a family vacation, large enough to accommodate everyone under one roof. Just a quick walk to the beach, or bay, centrally located to access all that Anna Maria has to offer. Furnishings are a little dated, but functional. Would bring the family back.

Great stay!

Date of Stay:

We found this beach house very comfortable. Enjoyed our stay! Would definitely come back.

Spring break 2019

Date of Stay:

We loved staying here! It was accommodating to our needs spacious and homey. Clean and cozy! Alex was very good to work with. He communicated very well with me in answering any questions I had. Will be back for sure.


Date of Stay:

We had a great time. We loved the house. The outdoor shower is a great feature.

Very clean house and looks just like the pictures. Beautiful

Date of Stay:

Loved drinking coffee on the front porch and beach a short walk away. House was big enough for family of 9 and did not feel like you were crowded. Hoping to come back!

Pirates Nest

Date of Stay:

Nice setting, comfortable and private house. Outstanding balconies and decks! Convenient to the beach, or the bay by walking about a block. A nice playground for kids across the lot. We had a great Christmas at the beach! With a quick store a block away, and major groceries and liquor stores within a mile, we could stay in the area the whole stay and maximize beach time! Would definitely come back some year!


Date of Stay:

It was like being home. Comfortable beds, plenty of towels and spacious. We had six adults and we were very comfortable. Walking distance to the beach and the trolly is a short walk to a stop. I would love to stay here with my kids and grandkids one day.

Great Stay

Date of Stay:

We had a great time on Anna Maria Island, not many people on the island during September and a few shops and restaurants were closed. The manager told us its the first month in the year that is considered off season. The home was very spacious and slept the six of us just fine. One of the downstairs bedrooms is a bit dark without opened window shades, but overall we were happy with our choice in accommodation and plan to spend more time on the island next year.

VERY disappointing - poor condition

Date of Stay:

The walk to the beach is truly ~ 2 minutes, and Alex, the property manager, was very good to work with and the newish Samsung TV worked well. BUT, by day 3 or 4 we summed it up: “This house is the CLEARANCE aisle at Walmart, many basic necessities are missing & what’s left are scratch/dent leftovers & cheap crap”. Virtually every bed & bath door squeaks, beds creak, 1/2 the ceiling fans wobble, chirp or tick. It’s hard to sleep. Notice both 6-position tables (dining and front deck) have 5 chairs. The house sleeps 10, yet only 1/2 can sit at the same table for a meal. Cookware is the cheapest quality available. Pan surfaces are tiny forests of Teflon flakes yearning for your scrambled eggs or attach to your child’s grilled cheese. The chef/prep knives for slicing & chopping belong in Dollar General’s reject bin as all 4 would be recalled by the Chinese govt for failing basic. Potholders, cookware lids, and even the bars on the inside of the refrigerator door – all MISSING! The living room furniture looks nice in the photos, but know they seem sourced at an estate-sale and old enough to hold a driver’s license. The blankets on the chair is to hide the torn leather that was poorly addressed by someone’s farsightedness and mismatched thread. If internet connectivity is important for uploading photos, YouTube videos longer than a few minutes, or your fam includes people ages 14 to 60, know the property owner offers the cheapest & slowest service available. I tested ~8mbps. Beyond missing & torn amenities, the clothes washer is of tiny capacity, mold cakes the inner workings around the detergent tray, and even the partially deaf can hear the unit running from any location within the house. No washing at nt time. It is impossible to pull into the driveway with a small sedan or VW Golf, exit the vehicle and enter the house without scratching paint or being assaulted by limbs and branches from the attractive, yet overgrown landscape. The living room temp is reasonably cool but the single small AC vents in each bdrms result in hot humid nts. I believe it is reasonable expect a rental property will be equipped and kept to at least the std implied by the $$, photos and mktg of the property. In my opinion, this house is an example of, “we own investment property but we don’t stay there”. Buy cheap and 2nd hand, discount 5-10% less than other houses. I say, do it well or don’t bother, , and that’s why I would dissuade from renting PNest Owner's Response: Thank you for your feedback. We have addressed some of the issues already, have been in touch with the owner about others and are happy to say that since the review our Pirates Nest has seen some updates. The interior and exterior of the home have been painted, decks have new fences, more lighting is now provided in bedrooms, and some kitchen items have been replaced. We had met the guests the very first day because the upstairs thermostat needed replacing, the temperature could not be set to warmer than 72 degrees anymore. During our chat the guest had stated that they often stay at vacation rental properties for family gatherings, but are used to more upscale and recently remodeled homes with amenities including stainless steel appliances, granite counter tops etc.. Realizing that our Pirates Nest is a bit more dated and not comparable we let the guest know that we would of course immediately address anything of concern. The guest reassured us that things were fine and that they would let us know if they needed anything, but we unfortunately never received a call or email. Small maintenance items such as two squeaking doors, some cookware that required replacing etc. were quickly corrected and the internet speed test indicated 12 mbs download speed, which is sufficient for streaming high definition movies (requires 5 mbs), but we realize that upload speeds tend to be much slower and could present a challenge if several users attempt to upload videos you Youtube. The upstairs AC unit was able to cool bedrooms into the low 70's even with very hot and humid outside weather conditions and the pictures show the furniture in the home. The dining and living room unfortunately do not offer more space to seat all guests at once and the home's price point is discounted considerably more than just 5-10% when compared to newer homes. We believe our Pirates Nest has a lot to offer to guests at the advertised price point and if we would have know of the guests past rental history we would have been more than happy to steer them into a different direction, as our guests experience truly is important to us.


Date of Stay:

Great week! Nice place. A short walk to the beach. We would stay again.

Perfect for pet owners and large groups!

Date of Stay:

We had an amazing family vacation here and the house suited our needs perfectly (all 10 of us). Very quick walk to the beach, just two blocks up (really less than that-- 2 to 3 min walk) and on a great part of the island near restaurants and shops. The house was way more spacious than expected and each room is situated near an outdoor space which gave it a cozy and private feel. The best part is how pet-friendly the house is set up. The outside areas are secured and enclosed with room in the back and front for your fur babies to run around. We were so pleased. Great vibe here :) I'm sure we'll return, and would definitely recommend this for larger groups looking for an affordable, clean and comfortable vacation spot close to the beach.

Very relaxing. Comfortable

Date of Stay:

Loved the privacy and the porches/patios. Mattresses were too firm. Need better pillows. Great location with easy access to park, bay and gulf beach. Great place for our multifam to be together and hang out.

Perfect place for our family

Date of Stay:

Thanks for a wonderful Thanksgiving retreat. This is our third Thanksgiving beach getaway, and we think we found the perfect place (others were charming but a tad claustrophobic). The Pirates Nest provided plenty of private sleeping space and gathering space for nine guests. We loved especially hanging out in the front and back porches. Our only disappointment was something beyond the capacity of the owner/manager to fix: more clouds than sun during our stay!

Felt like home

Date of Stay:

Great house, space for ten with little kids!

Great Cottage

Date of Stay:

Had a nice time staying at Pirates Nest. It is convenient to everything and just a couple blocks to the Gulf. It needs some updating, however, was very clean. And, no bugs!

Pirates nest vacation

Date of Stay:

This was our first attempt at a full family vacation and it was very good. We had several family groups together for spring break week. All were entertained with the beautiful beaches, Busch gardens, and just simply relaxing? The staff (Alex) was extremely helpful and the accommodations were ready to go! Would definitely choose them again in the future.

Island getaway!!!

Date of Stay:

Big house with all you need for a great vacation. Literally less than 5 minutes from the beach. Close to stores, dining and nightlife. Enjoyed every minutes of our stay.

Wedding Week & 50th BirthdayTrip

Date of Stay:

We really enjoyed the Pirates Nest. It was clean and in a good location, walking distance to beach or bay. The rental company and Megan were very easy to work with. We especially enjoyed the sunrise view from bed in the master as well as the huge closet! We certainly would recommend to a friend and would stay there again. My only complaint was that the home was advertised as having a hot-tub and there was not one when we got there. The owners refunded us a very small amount back, but was still disappointed. There were some staples not available in the house that we had to buy like toilet paper, which I thought was odd. Also, no basics like salt & pepper in the kitchen or a pan for biscuits. There was not a broom either, which bugged me, because we were there for 7 days and I would have liked to sweep up. All are little things, and it did not hinder our fun time on the island. I wish that I had read their recommendation to visit Bean Point earlier in our stay. It is the most beautiful place on the island!! Make sure to get to The Sign of the Mermaid for breakfast.

Great Wedding Vacation with Friends & Family

Date of Stay:

The place was in a great location with a very short walk to the beach. Loved all the outdoor seating areas to enjoy the gorgeous weather. Lots of sleeping options as well. Everyone really enjoyed their stay. My only suggestion is to inform future guests there is no longer a hot tub!!(Although who needs a hot tub when you have the beach)


Date of Stay:

It was really nice loved everything about it

Perfect Nest for a Family Getaway for a 50th Surprise Celebration

Date of Stay:

The house has so much character, so many rooms, and plenty of outdoor spaces for enjoying the gorgeous beach weather. Very affordable for the amount of bedrooms. The many trees and plants in the front and back yards make for a really secluded getaway. We enjoyed the park across the street, there's a decent playground, picnic tables, and a great view of the water. The few minutes it took to get to the beach made it easy to go back and forth throughout the day. The fully equipped kitchen made it real easy to dine in for breakfast, lunch and dinner. The welcome supplies made it easy to move right in. We enjoyed our stay so much I am sure we will be back again and again!

Fabulous Place for Family Reunion

Date of Stay:

he house is lovely, beautifully decorated, and impeccably clean. The management provided many touches to make the house very comfortable for a group. The kitchen had all the dishes, glasses, flatware, utensils, and appliances we needed. A washer and dryer are conveniently in the kitchen. When we arrived, the house was cool, the living room fan and TV were on. We felt very welcome! We look forward to staying again. Thanks so much!

Pirates Nest

Date of Stay:

We were thrilled w this house. Ideal space for a large group and plenty of towels for the beach! Close to beach, gym, grocery stores. Would stay here again for sure.


Date of Stay:

We had five families in five rooms for five days for a local wedding. Pirate's Nest was perfect, management responsive and accommodating. Not fancy, but very comfortable saved us a lot of money relative to other options in the area. Thanks so much for a great time!

Birthday Fun

Date of Stay:

We rented this home for my brothers 40th birthday. Great days at the beach followed by grilling in the back yard. It had everything we needed for a weekend away. The front porch was perfect to put our sandy stuff from the beach. We didn't fine the outdoor shower in the back yard until the 3rd day! Woops! But once we did, it was great. The house has great vibes. We were all comfortable and happy. Thanks for the sweet welcome bag too, Island Dreams! Response

Awesome Location!

Date of Stay:

We had a great vacation. This is exactly what we were looking for. The house was cute and a perfect distance from the Gulf. If you are looking for a place to relax, this is it!!I only wish the hot tub would have still been on the property. I think we found our place to start making memories.

Last minute getaway

Date of Stay:

We decided to tack on a few days to our conference in Orlando and head down to AMI. Property was the cleanest we've ever seen a vacation rental. Manager was great; smooth booking even though it was last minute. We would recommend to anyone who wants to be close to the beach and sleep in a nice clean bed with the AC pumping. If you rent, go sit on the benches on the bay and watch the boats. We really enjoyed that.


Date of Stay:

This was a perfect vacation home. Literally a two minute walk to the beach. We had plenty of room to spread out in the house. The beach is clear and very relaxing. The only thing missing was a hot tub but other than that it's a great place. We will be back

Family getaway

Date of Stay:

Pirates Nest was a blast for my family! With 4 kids there was plenty of space for everyone. The kids enjoyed the park down the street and the walk to the beach was very quick and easy. We practically lived on the big front porch. We have booked for next year and plan to bring my sisters two kids with us. Lots or room and so much fun!

Florida fun

Date of Stay:

Pirates Nest was a last minute trip but having stayed with Island Dreams a few other times we knew we were in good hands. We were bummed at first that there wasn't a pool, but you can't beat the quick walk to the beach and to the bay. There is a sweet little park right on the bay with a basketball court, swings, and all kind of fun stuff for the kids. Since it was early November, we didn't miss a thing without a pool. It's so peaceful in the back yard! Nice clean house. We loved all the windows!

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