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!
- 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.
Our prices include all fees. No hidden fees.
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Amenities
Pool
Hot tub
Kitchen
Washing machine
Dryer
Free WiFi
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This property is managed by a professional host. The provision of housing is linked to their trade, business or profession.
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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
If you cancel your booking, you'll be subject to the host's cancellation policy. In accordance with UK consumer law, property booking services are not subject to the right of withdrawal.
About the area
Anna Maria
Located in Anna Maria, this holiday home is near the beach. The area's natural beauty can be seen at Bradenton Beach and Bean Point Beach. Fish Hole Adventure Golf and H2O Watersportz are also worth visiting. Jet skiing and kayaking offer great chances to get out on the surrounding water, or you can seek out an adventure with hiking and horse riding nearby.
Anna Maria Island Museum and Historical Park - 5 min walk - 0.4 km
Anna Maria City Pier - 11 min walk - 1.0 km
Bean Point Beach - 17 min walk - 1.4 km
Getting around
Sarasota, FL (SRQ-Sarasota-Bradenton Intl.) - 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
Frequently asked questions
Is Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach?
As of 14 Apr 2026, prices found for a 1-night stay for 2 adults at Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach on 13 Jun 2026 start from £826, 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 at Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach?
On-site parking is available at the property.
What time is check-in at Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach?
Check-in begins at 4:00 PM.
What time is check-out at Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach?
Checkout is at 10:00 AM.
Where is Luxury Home with Pool, Rooftop Deck, and Gulf Views! 1.5 Blocks to Beach located?
Situated by the sea, this holiday home is within a 15-minute walk of Bradenton Beach and Bean Point Beach. Palmetto Avenue Beach and Island Players are also within 5 minutes.
Reviews
9.6
Exceptional
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
The house was lovely and perfectly located near the beach, shopping and restaurants. The host was very responsive when we contacted them for assistance.
Lori S.
Stayed 7 nights in Jan 2026
Response from VrboOwner on 26 Jan 2026
Hi, Lori, thank you for the kind review! We’re so glad you enjoyed your stay at Montego Bay with AMI Locals. That convenient location near the beach, shops, and restaurants makes it easy to enjoy the island, and we’re happy our local team was there when you needed them. We’d love to welcome you back for another Anna Maria Island getaway!!
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
Karen C.
Stayed 3 nights in Feb 2026
Response from VrboOwner on 24 Feb 2026
So glad you had a great time, Karen! We’re happy the home was a perfect fit for your crew and that you loved being able to walk to the beach, restaurants, and shops that’s the sweet spot for island living. And thank you for the note on cleaning supplies. We do provide starter essentials, but we really appreciate the feedback and will pass it along to the team. Hope to welcome you back for another easygoing AMI getaway soon!
Verified
8/10 Good
Lora K.
10 Mar 2026
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
Lora K.
Stayed 6 nights in Feb 2026
Response from VrboOwner on 6 Apr 2026
Thank you for staying at Montego Bay by AMI Locals, Lora. We’re so glad to hear you found the home nice, clean, and comfortable, and that our team was able to jump in quickly to take care of the water heater and pool that’s what we’re here for. We appreciate your feedback as well. We’ll be sharing your notes on the bunk beds and yard/beach games with the owner, and we’re happy to provide additional blankets anytime, just a quick message and we’ll bring some by. For kitchen items, we provide a starter setup, but we understand how having a few extras like spices or filters can make things feel more like home. Thanks again for your helpful suggestions and we’d love to welcome you back for another easy, fun island stay!
It worked so well for our group of 12 (ages 2 years to adults). Outside space was awesome. Beds were great!
Jessica D.
Stayed 5 nights in Oct 2025
Response from VrboOwner on 27 Oct 2025
Hi, Jessica, so glad to hear Montego Bay was a great fit for your whole crew! Sounds like everyone from the little ones to the adults had an awesome time, that outdoor space really is perfect for making memories. Thanks for staying with AMI Locals, and we hope to welcome your group back for another fun island getaway soon!!
Thank you for your review. We are pleased to hear that you would stay with us again. Your feedback is valuable as it helps us improve our services and ensure our guests have an enjoyable experience. We look forward to welcoming you back in the future.
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!
Brittney J.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 21 Jul 2025
Hi, Brittney, thank you for your kind review! We're thrilled to hear that you've enjoyed your multiple stays at our property and that the location and amenities have been a perfect fit for your vacation needs. We appreciate your loyalty and look forward to welcoming you back for many more comfortable and memorable visits in the years to come.
Thank you,
AMI Locals
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.
Curtis B.
Stayed 7 nights in Jun 2025
Response from VrboOwner on 14 Jul 2025
Hi, Alyson, thank you for your thorough review of the property. Here at AMI locals, we appreciate the feedback and are glad to hear that you enjoyed the convenient location, clean accommodations, and amenities like the pool! The pool alarms are a mandatory amenity for all vacation rentals on the island that has a door leading to a pool area for safety. Your satisfaction is important to us, and we hope you had an overall enjoyable stay. We look forward to the opportunity to host you again in the future, with AMI Locals.
Thank you,
AMI Locals
Kitchen in need of newer pots and pans more silverware , a bike or two could use a basket and beach chairs need updating
Beverly B.
Stayed 6 nights in May 2021
Response from VrboOwner on 21 Jun 2021
Thank you very much for staying with us Beverly! We continously update and we are appreciate of the feedback to help us stay on top of these things. We love hosting you and hope that you will return to us on your next trip to the islands. You definitely chose a great property and location. Very popular for sure.
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.
Patricia T.
Stayed 7 nights in Oct 2020
Response from VrboOwner on 1 Jul 2021
We want to thank you Patricia on your past stay with us! We strive to provide the utmost care for our guests needs and relieved to hear your small issues were resolved. We would love for you to come back again as you were fabulous guests!
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!!!!
Jenn A.
Stayed 7 nights in Aug 2024
Response from VrboOwner on 12 Dec 2024
Thank you for such a glowing review! We’re delighted to hear that check-in and check-out were a breeze and that you enjoyed the gorgeous home and all its amenities. It’s wonderful that the pool was perfect for your whole family and that the location made exploring the beach and nearby shops so easy. We’re also glad our team could quickly resolve the plumbing issue for you. We’d love to welcome you back anytime—hopefully in the very near future!
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.
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.
Michelle K.
Stayed 7 nights in Mar 2021
Response from VrboOwner on 23 Apr 2021
Thank you so much for your feedback Michelle. Lots of helpful suggestions that will help us be better than ever! We love making our guests happy and makeing sure that you have everything you need. We are very happy that you enjoyed your stay and hope that you will allow us to host you again on your next adventure to our amazing islands.
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!!!
Todd W.
Stayed 4 nights in Apr 2024
Response from VrboOwner on 13 May 2024
Todd, it sounds like you had an absolutely fantastic vacation! We're thrilled to hear that the property exceeded your expectations and provided everything you needed for a memorable stay. The modern updates, unique amenities, and multiple outdoor decks, including the rooftop deck for morning sunrises, all sound wonderful. We're delighted that the pool and backyard landscaping were impressive and enjoyed by your family after beach days. It's great to hear that the spa provided warmth and relaxation in the evenings.
The proximity to the beach and nearby coffee and ice cream shops sounds ideal, and we're glad to hear that any maintenance questions were promptly addressed by the property management team. We're honored to have been a part of creating lasting memories for your family, and we look forward to welcoming you back to Anna Maria Island in the future! If you have any further comments or questions, please feel free to let us know.
Verified
6/10 Okay
Melanie J.
10 Jul 2024
Liked: Check-in, location, listing accuracy
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.
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!!
Erika R.
Stayed 4 nights in Feb 2026
Response from VrboOwner on 20 Feb 2026
Thank you so much for sharing this about Montego Bay by AMI Locals, Erika! We love hearing how much your family enjoyed the tropical vibes, pool time, and those peaceful balcony moments. Being able to walk to the beach, restaurants, and ice cream really is what island life is all about. Thanks as well for the notes on the pool alarm and small touch-ups — the alarms are required for safety, and we’ll definitely share the maintenance feedback with our team to keep things feeling fresh. So glad this home helped make your AMI trip magical. We’d love to host your family again anytime!
Everything was very good except the check out too early
Alberto P.
Stayed 2 nights in Oct 2025
Response from VrboOwner on 28 Oct 2025
Hi, Alberto, thanks for sharing your feedback! We’re glad you enjoyed your stay at Montego Bay and appreciate your note about check-out time. Our AMI Locals team will keep that in mind as we continue to improve the guest experience. We hope to welcome you back for another great stay soon!
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.
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.
Great house, great location! Perfect for families!
Ronald P.
Stayed 3 nights in Sep 2021
Response from VrboOwner on 28 Sept 2021
Ronald, thank you for choosing your island getaway with us! So happy the home was a perfect fit for all! We welcome you back anytime. You were fabulous guests.
We had an amazing week with amazing amenities! The pool area and decks were a plus as it was sometimes too windy to be at the beach. Would definitely book here again!
The water pressure was bad as others stated but after we called the first night it was fixed with no problems.
Christy V.
Stayed 7 nights in Feb 2020
About the host
Hosted by AMI Locals
Languages:
English
Premier Host
They consistently provide great experiences for their guests