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Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach

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A heated pool
Terrace/patio
Fridge, microwave, oven, stovetop
Exterior
Dining

Reviews

9.6 out of 10
Exceptional

Entire home

5 bedrooms4 bathroomsSleeps 12242 sq m

Popular amenities

  • Pool
  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi

Explore the area

View map
Anna Maria, FL
  • Place, Bradenton Beach
    ‪3 min walk‬
  • Place, Anna Maria Island Museum and Historical Park
    ‪5 min walk‬
  • Place, Bean Point Beach
    ‪17 min walk‬
  • Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
    ‪45 min drive‬

Room options

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About the area

Anna Maria

With a stay at this vacation home in Anna Maria, you'll be by the sea, a 4-minute walk from Bradenton Beach and 15 minutes by foot from Bean Point Beach. .This vacation home is 12.3 mi (19.8 km) from IMG Academy and 20.6 mi (33.2 km) from Tampa Bay.
View more Holiday homes in Anna MariaOpens in a new window

What's nearby

  • Bradenton Beach - 3 min walk - 0.3 km
  • Island Players - 5 min walk - 0.4 km
  • Anna Maria Island Museum and Historical Park - 5 min walk - 0.4 km
  • Anna Maria City Pier - 12 min walk - 1.1 km
  • Bean Point Beach - 17 min walk - 1.4 km

Getting around

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

Restaurants

  • ‪Anna Maria Island Beach Cafe - ‬8 min drive
  • ‪The Ugly Grouper - ‬5 min drive
  • ‪The Sandbar Restaurant - ‬4 min walk
  • ‪The Waterfront Restaurant - ‬10 min walk
  • ‪Ginny's & Jane E's - ‬1 min walk

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach

Montego Bay by AMI Locals
VPR16-000472

Escape to Montego Bay, an Anna Maria Island vacation home with a private pool, rooftop deck with Gulf views, and multiple balconies designed to give you the ultimate experience! This spacious five-bedroom, four-bath home is just one and a half blocks from the north end of the beaches and Pine Avenue’s shops and restaurants, allowing you to indulge in the best of Anna Maria Island with your own personal, luxurious touch. Surrounded by tropical breezes and scenic water vistas, this home is perfect for creating lifelong memories whether relaxing on the balcony, dining in the backyard, or exploring the island!

Highlights
• 4 minutes / 1.5 blocks to Anna Maria Beach
• 5 Bedroom / 4 Bath
• 4 King beds, 2 twin/twin bunks
• Private pool with sun shelf and hot tub
• Rooftop deck with Gulf views
• Outdoor living space
• Outdoor TV and dining table
• 4-minute walk to Pine Avenue’s boutique shops and waterfront restaurants
• Washer and dryer
• 4 Parking spaces

Relax outdoors in your tropical backyard oasis, lounge poolside on the sun shelf, enjoy a family cookout at the BBQ grill, or unwind on the balcony with a good book or evening cocktail. The spacious covered lounge offers a TV and outdoor seating, while the rooftop deck provides breathtaking tropical views and spectacular sunsets.

Inside, the home features a bright, open-concept main living area with coastal decor, comfortable seating, and large windows framing water views. The fully equipped kitchen with stainless steel appliances, ample counter space, and a large island is perfect for island-inspired cooking or casual snacks. The dining area seats eight and overlooks the backyard and pool, ideal for meals and socializing in style.

Retreat to the primary bedroom on the second floor, complete with a king bed, ensuite with dual vanity sinks, walk-in shower, and balcony access to enjoy peaceful Gulf vistas. The second bedroom, also on the second floor, boasts a king bed, ensuite bathroom with walk-in shower, and balcony views. The third bedroom provides a king bed and balcony access, while the fourth bedroom has a king bed, both sharing hall bathrooms with walk-in showers. The fifth bedroom, perfect for kids or additional guests, features two twin bunk beds, with a hall bathroom containing a combined shower and tub, all with premium linens and TVs for restful nights.

Room Details
• Primary Bedroom (2nd floor): King bed, ensuite bathroom with walk-in shower, dual vanities, balcony
• Second Bedroom (2nd floor): King bed, ensuite with walk-in shower, balcony
• Third Bedroom (2nd floor): King bed, balcony access
• Fourth Bedroom (3rd floor): King bed
• Fifth Bedroom (3rd floor): Two twin bunk beds

Take a leisurely stroll to nearby beaches, shops, and waterfront dining, or hop on the free trolley to explore all seven miles of Anna Maria Island, from secluded Bean Point to Coquina Beach.

Book Montego Bay today and enjoy a luxurious escape in the heart of Anna Maria Island. With stunning Gulf views, outdoor amenities, and proximity to beaches and shops, this estate offers everything you need for a memorable, relaxing vacation. Reserve your dates now and create lifelong beach memories!


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There are no pets allowed in this home.

4 cars maximum can park at this home. We ask our guests to please plan accordingly and coordinate with your group. There is no overnight parking available for additional vehicles.

This home is managed by AMI Locals, an Anna Maria Island property management company.

We do not accept reservations from anyone under 25 years of age. We do not allow persons under 25 to occupy a property unless accompanied by someone over 25 years of age.

Please see our AMI Locals Rental Policies for full details.

Please Remember: "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." *Exceeding the noise ordinance could result in disciplinary actions including fines and/or termination of your rental agreement without refund.
Make yourself comfortable in this air-conditioned vacation home, which features a private pool and a flat-screen TV. There's a private balcony or patio. A kitchen is outfitted with a refrigerator, an oven, and a stovetop. Complimentary wireless internet access is available to keep you connected.
Enjoy recreation amenities such as a hot tub or take in the view from a rooftop terrace.
Guests will find features like internet access and onsite parking.

Property amenities

Beach

  • Beach nearby

Pool/Spa

  • Heated pool
  • Hot tub
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Ice maker
  • Kitchen island
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 4 private bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table
  • Living room

Entertainment

  • Flat-screen TV with cable/satellite channels
  • Video games

Outdoor areas

  • Balcony
  • Barbecue grill
  • Fenced yard
  • Rooftop terrace

Laundry

  • Laundry facilities
  • Washer/dryer

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Services and conveniences

  • Iron/ironing board

Location highlights

  • Near a health/beauty spa
  • Near a hospital
  • Near an outlet shopping centre
  • Near the marina
  • Near the sea

Things to do

  • Heated pool
  • Basketball nearby
  • Birdwatching nearby
  • Ecotours nearby
  • Fishing nearby
  • Golfing nearby
  • Hiking/biking trails nearby
  • Horseback riding nearby
  • Jet skiing nearby
  • Kayaking nearby
  • Motor boating nearby
  • Parasailing nearby
  • Sailing nearby
  • Snorkelling nearby
  • Surfing/bodyboarding nearby
  • Swimming nearby
  • Wildlife walks nearby

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher
  • Deadbolt lock

General

  • Unit size: 2,600 square feet

Policies

Check-in

Check-in time starts at 4:00 PM

Contactless check-in available

Minimum check-in age: 25

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions

Information provided by the property may be translated using automated translation tools

Pets

Pets not allowed

Children and extra beds

Children are welcome

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 indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadbolt lock
This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

Property is also known as

Beautiful Water Views Amazing Roof TOP Deck Private Spa House

Beautiful Water Views Amazing Roof TOP Deck Private Spa

Beautiful Water Views Amazing Roof TOP Deck Private Spa House

Beautiful Water Views Amazing Roof TOP Deck Private Spa House

Vacation Tropical Paradise Water Views Roof Top Deck House

Vacation Tropical Paradise Water Views Roof Top Deck

Vacation Tropical Paradise Water Views Roof Top Deck House

Vacation Tropical Paradise Water Views Roof Top Deck

Montego Bay Five Bedroom House Sleeps 11

Beautiful Home Great Location Just 5 min Walk to Beach!

88

Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 31 out of 40 reviews
Rating 8 - Good. 7 out of 40 reviews
Rating 6 - Okay. 2 out of 40 reviews
Rating 4 - Poor. 0 out of 40 reviews
Rating 2 - Terrible. 0 out of 40 reviews

9.2/10

Cleanliness

Reviews

10/10 Excellent

Lindsey S.

Liked: Cleanliness
We absolutely loved our stay!
Stayed 5 nights in Apr 2026

8/10 Good

Lora K.

Home was nice, clean, and comfortable beds, minus the bunk beds. Water heater element was out, but they did come fix it. Pool had an issue but they came and fixed that as well. We were wishing for more blankets, and kitchen supplies, such as spices. In past Vrbo homes, kitchens have some of the basics, such a spices, sugar, coffee filters. Ami locals company was very prompt on issues and helpful. Some yard/beach games
Stayed 6 nights in Feb 2026

10/10 Excellent

Karen C.

Liked: Cleanliness
The host was excellent in responding and communicating. The house was perfect for our family and walking distance to beach, restaurants, and shops! Had a great time.Only wish there were some cleaning supplies like windex and countertop cleaner for daily use
Stayed 3 nights in Feb 2026

10/10 Excellent

Erika R.

Liked: Cleanliness
Our stay at this home was so wonderful! Tropical vibes, relaxing, homey. We all loved the pool and felt like we were in another world. We spent most of the kids nap times with the bedroom balcony doors open- reading, resting, enjoying the breeze and sounds of the island. We loved how close we were to the beach and restaurants and ice cream. We basically walked everywhere. The pool siren is a little aggressive but isn’t unique to this home. We occasionally heard other houses in the area’s pool alarms going off and it made us chuckle. Not a problem for us at all, but something for another occupant to be aware of. There were some things in the house that show it is well loved. Some of the fixtures that could be tightened, fresh paint touch ups at some point and fresh lightbulbs. All things that didn’t change the quality of our stay at all, but could freshen up the home a bit. Overall we loved our stay on Anna Maria Island and this house was a big reason it was so magical!! Thank you AMI Local!!
Stayed 4 nights in Feb 2026

10/10 Excellent

Lori S., Iowa

Liked: Cleanliness
The house was lovely and perfectly located near the beach, shopping and restaurants. The host was very responsive when we contacted them for assistance.
Stayed 7 nights in Jan 2026

8/10 Good

Alberto P.

Liked: Cleanliness
Everything was very good except the check out too early
Stayed 2 nights in Oct 2025

10/10 Excellent

Jessica D.

Liked: Cleanliness
It worked so well for our group of 12 (ages 2 years to adults). Outside space was awesome. Beds were great!
Stayed 5 nights in Oct 2025

10/10 Excellent

Brittney J.

Liked: Cleanliness

Multi group family stay

This is our 3 year staying at this property. The location cannot be beat! We enjoyed, as always the super close proximity to the beach and walked multiple times a day. The property itself, outside of light wear, is well maintained and stocked. We always enjoy this house!
Beach couldn’t be more beautiful
Stayed 7 nights in Jun 2025

8/10 Good

Curtis B.

Liked: Cleanliness

Great location

The house is situated in a great location with access to rental equipment, places to eat and beach access. The pool was nice to come back to after a long day at the beach. The house was clean with plenty of space. Our only complaints would be the third floor was extremely humid and hot and it took a few days to get used to the pool alarms anytime you wanted to exit the rear of the house. It was nice not having to rent beach chairs or a beach wagon.
Stayed 7 nights in Jun 2025

10/10 Excellent

Bradley J., Frankfort

Liked: Cleanliness

Great family vacation

The location is perfect to walk to the beach, breakfast & dinner places. Only needed a car to get groceries.
Stayed 5 nights in May 2025

8/10 Good

Michael C.

Liked: Cleanliness

Good house

We would stay again
Stayed 6 nights in Mar 2025

10/10 Excellent

Jenn A.

Liked: Cleanliness

Fantastic in every way!!!!

Checkin and check out were a snap! Gorgeous home with everything you can think of. Pool was a great size for the whole family. Right in the middle of everything!!! Half a block to the beach and all the adorable shops!!! There was a small plumbing issue and they were there within 1 hour of our call to do a quick fix. I would go back in a heartbeat!!!!
Stayed 7 nights in Aug 2024

6/10 Okay

Melanie J.

Beware the upstairs is humid and the bunk room stays hot

When we arrived, I was excited for the location and convenience of the home. However, the home was not cleaned very well - lots of hair in the shower, kitchen counters and table were not wiped/cleaned all the way, and just seems like the place also needs a deep cleaning (baseboards in several places were very dirty). This was reported to the local management company. Also, we reported daily about the upstairs A/C not working properly - upstairs was very humid feeling and warm. The local management company was quick to respond, however, the technician indicated the HVAC company would need to come. They did and added Freon but indicated there may be a bigger issue with duct work. We continued to report the upstairs being humid and the bunk room is just too warm for anyone to sleep - the kids moved out of that room onto couches. We were told that we would get a portable a/c - never saw it. We actually went to the Ace Hardware and bought fans to try to help the situation. We were very disappointed in the upstairs A/C situation and the lack of a solution for our issue. Outside of the issues, we did enjoy our stay - huge garage for storing bikes, golf cart rental, cars and beach gear! Nice pool out back. Good rooftop.
Stayed 7 nights in Jun 2024

10/10 Excellent

Todd W.

Liked: Cleanliness

Memories for a Lifetime

Our large family stayed at this property and we had an amazing vacation. The home was beautiful with modern updates and had many unique amenities. There were multiple outdoor decks along with a roof top deck that was a hit for morning sunrises. The pool and backyard landscaping was very impressive and a hit with our family after a day at the beach. The spa heats up to very warm temps and was great at nights when the temps cooled a bit. The beach is literally just a few blocks away and a very convenient walk. The home included some beach chairs and sand umbrella. The beach with the white sand was a dream!! Coffee and ice cream shops were just around the corner from the house. We had a couple maintenance questions that AMI quickly responded to. Very responsive. We will definitely book this property the next time we visit Anne Marie Island. Thanks for the memories!!!
Stayed 4 nights in Apr 2024

10/10 Excellent

Verified traveller

Liked: Cleanliness

Labor Day weekend Stay

Great stay, very comfortable house in perfect location. Loved the size of the garage
Stayed 3 nights in Sep 2023

10/10 Excellent

Jorge V.

Liked: Cleanliness

Great location

Beautiful house have everything at walking distance great for families
Stayed 3 nights in Jul 2023

10/10 Excellent

Verified traveller

Liked: Cleanliness

Great house and location

We loved the house. The location was great. It was a quick walk to the beach and we loved having the pool and spa at the house. There were also several restaurants to walk to near by. The only negative thing I could say is the mosquito were horrendous in the backyard day and night. Also several of us were eaten up by fire ants that were living in the bricks around the pool. I would suggest bringing bug spray and citronella candles. Other than that we had a wonderful stay and would definitely come back.
Stayed 7 nights in Jun 2022

8/10 Good

doug w.

Liked: Cleanliness

Good location

Nice location and pool. Minor repairs needed on property. Minimum cooking pans and no pot holders. Fridge very slow to make ice. Quick response from property management when called.
Stayed 7 nights in May 2022

10/10 Excellent

Paul K.

Liked: Cleanliness

Heaven On Earth

This rental met and exceeded our expectations. The location to the beach was a hop skip and we loved the pool and hot tub in the backyard. The description of what comes with the house needs to be updated. We ended up not needing to rent a few items. The house does have a beach umbrella, plus over 7 adult bikes (we rented two kids bikes.) We purchased a pool noodle and a children's life vest (much needed! the pool is small but gets deep) and those were easily arranged thanks to the prompt concierge service that comes with the house. For an active rental, I wish the kitchen had salt. There was absolutely nothing available in the kitchen. I recommend you stock up on coffee filters (not just ground coffee), salt, oil, and any other main essential. Lastly, all the rooms were spacious and great. The only mattresses that were less than stellar were the full and twin mattresses on the bunk bed in the kids' room. Lastly, the drainage wasn't great but didn't pose a huge problem for us though I read in other reviews it was a bigger problem. Note that the drainage is slow. The heated outdoor shower was a plus though and the kids really loved it. Overall, highly highly recommend for a large family or bigger group, and hope to be back next year at this same property.
Stayed 4 nights in Feb 2022

10/10 Excellent

Bob C.

Liked: Cleanliness

A Great Visit

We had a wonderful stay. The staff at AMI Local was very friendly and helpful. Great location. We would highly recommend.
Stayed 7 nights in Jan 2022

10/10 Excellent

Ronald P.

Liked: Cleanliness

Awesome, easy family vacation spot

Great house, great location! Perfect for families!
Stayed 3 nights in Sep 2021

8/10 Good

Beverly B.

Liked: Cleanliness

Great house and location!

Kitchen in need of newer pots and pans more silverware , a bike or two could use a basket and beach chairs need updating
Stayed 6 nights in May 2021

10/10 Excellent

Michelle K., Roswell

Liked: Cleanliness

Anna Maria spring break 2021

The property is wonderful for multiple families. We loved our stay and the house was wonderful! Teens enjoyed the pool and hot tub. Location is walkable to all the hot spots on Pine and the beach. Property manager was very responsive when we had a flood due to some plumbing issues in the neighborhood. It would be very helpful if the listing can show what comes with the house - such as Beach towels, bikes, beach carts, umbrella, etc. since some of our party flew down- it’s super helpful to know for example- that we didn’t need to bring beach towels. Kitchen can use a few bigger pots for cooking pasta, etc. we borrowed stuff from a neighbor.
Stayed 7 nights in Mar 2021

10/10 Excellent

Patricia T., Seneca, SC

Liked: Cleanliness

Good spot

Great location. Can walk to shops, restaurants, great section f beach. House is spacious, well equipped, clean,- no complaints. Rental company was very responsive to our few problems (mosquitoes, clogged drain). Would definitely stay again. Also appreciated the stress free check in.
Stayed 7 nights in Oct 2020

10/10 Excellent

Yusiny D.

Liked: Cleanliness

Beautiful home. Comfortable beds. Well equipped and great location.

Loved our stay!!!
Stayed 7 nights in Jul 2020