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

Anna Maria, Florida
$899 avg/night
Bed 5

Bed

Bath 4

Bath

Home Private Vacation Home

Property Type

Sleep 12

Max Sleeps

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.

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  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    No Pets Allowed
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    5 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 2600 Sq Ft (242 Sq M)
  • KITCHEN

    Coffee/tea Maker Dishwasher Ice Maker Kitchen Island Microwave Oven Refrigerator Stovetop Toaster
  • LAUNDRY

    Laundry Facilities Near Laundromat Washing Machine And Dryer
  • PARKING

    Onsite Parking
  • INTERNET

    Free WiFi
  • OUTDOORS

    Balcony Barbecue Grill Fenced Yard Rooftop Terrace
  • POOL/SPA

    Heated Pool Hot Tub Private Pool
  • BATHROOMS

    4 Bathrooms Hair Dryer Towels Provided
  • LANGS SPOKEN

    English
  • THINGS TO DO

    Birdwatching Nearby Fishing Nearby Fitness Facilities Nearby Golf Nearby Horse Riding Nearby Jet Skiing Nearby Kayaking Nearby Power Boating Nearby Snorkeling Nearby Surfing/body Boarding Nearby
  • ENTERTAINMENT

    Video Games Flat-screen TV With Cable/satellite Service
  • LIVING SPACES

    Living Room
  • CLIMATE CONTROL

    Air Conditioning Heating
  • LOCATION HIGHLIGHTS

    Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Sea
  • SERVICES AND CONVENIENCES

    Iron/ironing Board
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 10:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 12

Map Map

School District Availability

Review Review

  • Lora K.

    Submitted Mar 10, 2026

    Stayed Feb 9, 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

  • Karen C.

    Submitted Feb 23, 2026

    Stayed Feb 19, 2026

    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

  • Erika R.

    Submitted Feb 19, 2026

    Stayed Feb 15, 2026

    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!!

  • Lori S.

    Submitted Jan 25, 2026

    Stayed Jan 16, 2026

    The house was lovely and perfectly located near the beach, shopping and restaurants. The host was very responsive when we contacted them for assistance.

  • Alberto P.

    Submitted Oct 27, 2025

    Stayed Oct 24, 2025

    Everything was very good except the check out too early

  • Jessica D.

    Submitted Oct 20, 2025

    Stayed Oct 14, 2025

    It worked so well for our group of 12 (ages 2 years to adults). Outside space was awesome. Beds were great!

  • Brittney J.

    Submitted Jul 7, 2025

    Stayed Jun 28, 2025

    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!

  • Curtis B.

    Submitted Jun 29, 2025

    Stayed Jun 21, 2025

    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.

  • Bradley J.

    Submitted May 23, 2025

    Stayed May 18, 2025

    The location is perfect to walk to the beach, breakfast & dinner places. Only needed a car to get groceries.

  • Michael C.

    Submitted Apr 8, 2025

    Stayed Mar 30, 2025

    We would stay again

  • Jenn A.

    Submitted Aug 18, 2024

    Stayed Aug 11, 2024

    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!!!!

Your dates are Available!

Total

Includes taxes and fees
$904+
View details