Four-bedroom vacation rental in Holmes Beach with a private infinity-edge pool, rooftop spa, and Gulf-view deck; a beach house rental near the island trolley for easy access to Anna Maria Island beaches.
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The Black Pearl is a 4-bedroom, 5.5-bath waterfront-view home in Holmes Beach, Florida, sleeping up to 8 guests across 2,030 square feet. It pairs a near-beach setting with standout outdoor features, including a private infinity-edge pool and spa/hot tub plus a rooftop deck with panoramic Gulf views. For getting around, the home includes bicycles and a six-seat golf cart, and it also offers games like ping pong and cornhole.
Inside, the layout centers on an open living area and a full kitchen with a large island, dishwasher, and standard small appliances. Sleeping is arranged with four king beds plus a sofa bed in a den. Each king bedroom has a private ensuite with a walk-in shower, and there is an additional bathroom with a tub/shower combination. Practical conveniences include air conditioning, WiFi, washer/dryer, keyless entry, towels/linens, and a fenced yard with outdoor seating, dining, grill, and an outdoor shower. Dogs are allowed with host approval (no cats).
Good fit for
Pet-friendly staysLong-term stays
Infinity Pool and SpaPrivate infinity-edge pool plus a spa/hot tub are provided on-site.
The Black Pearl is in Holmes Beach, Florida, on Anna Maria Island, with a waterfront-view setting and near-beach access. The home is in a residential street area, and the listing notes a nearby free island trolley stop for getting around the island. Guests are asked to keep noise to a respectful level due to the residential neighborhood setting.
Use the calendar as a guide, then confirm current availability directly with the manager.
Available Booked
About this rental
About This Rental
The Black Pearl is a waterfront-view vacation home in Holmes Beach on Anna Maria Island, set near the beach and designed for stays up to 8 guests. The home includes 4 bedrooms and 5 full bathrooms plus 1 half bath, with a sleeping setup of four king beds and a sofa bed. A key differentiator is the outdoor setup: a private black-bottom infinity-edge pool, a spa/hot tub, and a rooftop deck with panoramic Gulf views.
The main living space is arranged as a bright, open common area for gathering, with a full kitchen and dining area. Kitchen features include a kitchen island, dishwasher, refrigerator/freezer, stove/oven, microwave, toaster, blender, and both a standard coffee maker and a Keurig, along with dishes, utensils, pots, pans, wine glasses, and a baking sheet. For downtime at home, the property provides a television, internet access, and games including a ping pong table and cornhole.
Bedroom privacy is supported by ensuite bathrooms: the primary and the three additional king bedrooms each have a private ensuite with a walk-in shower. An additional bathroom with a tub/shower combination is also available, and the den provides the sofa bed for extra flexibility. Practical amenities include air conditioning, heating, hot water, towels/linens, hair dryer, iron/ironing board, hangers, and a washer/dryer.
Outdoor features include a fenced yard, patio and balcony areas, outdoor seating and dining, sun loungers, an outdoor shower, and a grill. The home also includes beach chairs, bicycles, and a six-seat golf cart for guest use (driver must maintain current U.S. auto insurance). Parking is limited to a maximum of 4 cars. Dogs are allowed with host approval (no cats), and the home offers contactless check-in and a keyless lock.
The Black Pearl by Exclusive Vacations
Vacation Rental License #VRC23-000114
Experience luxury and coastal elegance at The Black Pearl, part of our Exclusive Collection. This stunning black and white designed beach home offers a private black-bottom infinity edge pool and panoramic Gulf views. Located within walking distance of the pristine beaches of Holmes Beach and just steps from the free island trolley, this four-bedroom, five-and-a-half-bathroom home offers the ultimate Florida vacation experience. Perfect for families or groups seeking opulence, relaxation, and adventure, The Black Pearl provides guests with a premium stay and exclusive amenities.
Highlights
• 2-minute walk to the Beach Access
• 4 Bedroom / 5.5 Bath
• 4 Kings, 1 Queen sleeper sofa
• Corn Hole and Ping Pong
• Resort Style 360 Infinity Edge Pool and Spa
• Rooftop Deck and Panoramic Beach Views
• Outdoor Grill and Dining Area
• Dog Friendly with host approval
• Walking Distance to Downtown Holmes Beach Shopping and Dining
• 4 Parking Spaces
Exclusive Amenities
• 6 Seat Club Car Cru Golf Cart for Guest Use
• Luxury Beach Bikes for Guest Use
• Luxury Beach Chairs and a Beach Cart for Guest Use
• Upgraded Bed and Bath Linens and Toiletries
• Portable Pack and Play
Enjoy your private outdoor oasis featuring a 360 Infinity edge infinity pool, a rooftop deck with a spa, fire-pit, sweeping beach views, and an outdoor seating area perfect for sunset cocktails. The outdoor kitchen and grill create the perfect setting for poolside barbecues, while fun outdoor games like corn hole and ping pong keep everyone entertained. The house includes a luxury six-seat golf cart and four beach bikes, making exploring the island effortless and stylish.
The bright, open living area offers a tranquil retreat after a day at the beach, with inviting sofas, modern artwork, and abundant natural light. The gourmet kitchen features custom cabinets, stainless steel appliances, sparkling countertops, and a large island with seating, ideal for preparing meals and entertaining. The dining room provides beautiful views of the tropical landscape, perfect for family dinners or celebrating special occasions.
Each bedroom is designed for ultimate comfort and privacy. The primary suite features a plush king bed, spacious ensuite with a walk-in shower, and deluxe linens. The remaining bedrooms all have king beds and private ensuite bathrooms with walk-in showers, ensuring restful nights for everyone. An additional bathroom with a tub and shower combination is located on the third floor. The den includes a queen sofa bed, providing extra sleeping space, and a washer and dryer is available for added convenience.
Room Details
• Primary Bedroom: King bed, ensuite with walk-in shower
• Second Bedroom: King bed, ensuite with walk-in shower
• Third Bedroom: King bed, ensuite with walk-in shower
• Fourth Bedroom: King bed, ensuite with walk-in shower
• Bonus, Den: Queen sofa bed
Guests enjoy an outdoor shower, upgraded linens, and toiletries, along with complimentary beach chairs, beach cart, and bikes. The prime location steps from the trolley stop, allows easy access to all seven miles of Anna Maria Island beaches, shopping, dining, and outdoor adventures.
Book your stay at The Black Pearl today and immerse yourself in a perfect blend of luxury, outdoor fun, and island adventure. From sunset sails to dolphin sightseeing, and beachside lounging to exploring historic Bean Point, this home offers everything you need for an unforgettable Gulf Coast vacation. Pack your sunglasses and flip-flops and make The Black Pearl your island getaway. Reserve now and create lifelong memories!
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This home is managed by AMI Locals, an Anna Maria Island property management company.
With host approval before check-in, this property accepts dogs only (No cats or other animals are allowed). An additional pet fee will apply. See our Rental Policies for full details.
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.
Use of the provided golf cart requires the driver to maintain a current U.S. automobile insurance. Proof of insurance is required upon request.
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.
Before you book
Vacation Rental Policies
Check In
4:00 PM
Check Out
10:00 AM
Things to enjoy
Activities and Special Interests
This property provides access to the following activities and special interests:
Beach
Biking
Boating
Canoeing
Fishing
Deep Sea Fishing
Golfing
State National Parks
Ocean
Pet Friendly
Sailing
Scuba Diving
Surfing
Fly Fishing
Wind Surfing
Hiking
Luxury
Family Vacations
Kayaking
Other Activities and Special Interests
Tennis Court Nearby
Sailing Nearby
Surfing Nearby
Health Beauty Spa Nearby
Kayaking Nearby
Museums Nearby
Boating Nearby
Local Eco Tourism Nearby
Horseback Riding Nearby
Outlet Shopping Nearby
Wildlife Viewing Nearby
Fitness Center Nearby
Laundromat Close By
Hiking Nearby
Jet Skiing Nearby
Parasailing Nearby
Snorkeling Nearby
Swimming Nearby
Water Sports Nearby
Marina Nearby
Shopping Nearby
Bird Watching Nearby
What's included
Property Amenities
Featured Amenities
Air Conditioning
Dishwasher
Grill
Hot Tub
Internet Access
Pets Allowed
Pool (Private)
Television
Washer/Dryer
Property Features
Balcony
Blender
Ceiling Fan(s)
Coffee Maker
Freezer
Full Kitchen
Hair Dryer
Microwave
Oven
Refrigerator
Stove
Toaster
Towels/Linens
Entertainment
Ping Pong Table
Other Property Amenities
Holmes Beach
Anna Maria Island
Living Room
Dishes and Utensils
Fire Extinguisher
Heating
Hot Water
Long Term Stays Allowed
Private Entrance
Smoke Detector
Hospital Close By
Carbon Monoxide Detector
Deadbolt Lock
Pots and Pans
Contactless Check-In
Pack 'n Play
Backyard
Clothes Hangers
Iron and Ironing Board
Patio
Residential Street
Fenced Yard
Kitchen Island
Dining Table
Three (3) Parking Spaces
Bathtub
Cornhole
Keurig Coffee Maker
Keyless Lock
Outdoor Seating
Outdoor Shower
Rooftop Deck
Clothing Storage
Wine Glasses
Baking Sheet
Hot Water Kettle
Bicycles Included
Outdoor Dining Area
Sun Loungers
Beach Chairs Provided
Required Stairs
Guest feedback
Testimonials
We thoroughly enjoyed our stay at The Black Pearl
The backyard was a dream and we enjoyed the pool /spa daily along with the games. We also enjoyed using the included bikes and sightseeing around the island on the golf cart. The house is beautiful and very comfortable and fit our family. Each bedroom was like a mini suite! Thank you to the property management group for their continuous check-ins to make sure all was well. Everything went very smoothly. We would highly recommend and hope to return again to Anna Maria Island/Holmes Beach.
Cynthia
Posted: 6/5/2026
We had an amazing stay at the Black Pearl!
Everything was clean and exactly as described. The location is perfect—close to restaurants and bars, and just a short walk to the beach. The rooftop views were incredible. Would definitely recommend this spot for your next vacay!
Neely
Posted: 6/5/2026
We had an amazing stay at the Black Pearl! Everything was clean and exactly as described. The location is perfect—close to restaurants and bars, and just a short walk to the beach. The rooftop views were incredible. I do wish the hot tub was a bit easier to heat up, but it was still enjoyable. Would definitely recommend this spot for your next vacay!
Neely
Posted: 1/31/2026
What a pleasure to host you at The Black Pearl, Neely! We’re so glad the home felt just as it should—beautifully prepared, thoughtfully appointed, and perfectly placed for evenings out and easy beach mornings. Those rooftop views really are something special, especially as the sun slips down over the island. Thank you as well for the note on the hot tub—we’ll take a closer look to ensure it’s as effortless as the rest of the experience. We’d be delighted to welcome you back for another stay with Exclusive AMI—your next escape will be waiting.
Exclusive Vacations staff
Black Pearl
The property was beautiful!! From the pool area to the amazing interior we loved everything about it!!
Melissa G.
Posted: 10/27/2025
Perfect vacation home
Our stay at this fantastic 4-bedroom vacation home on Anna Maria Island was absolutely incredible. This place had everything we could ask for and more! The private pool and spa were beautiful and unique, perfect for relaxing, and the rooftop deck provided stunning views… especially for watching the famous Florida sunsets with our group of friends. The interior design was top-notch, with a classy touch that made the whole place feel luxurious and comfortable. Each bedroom was a plush retreat, and the fully equipped kitchen made group meals a breeze. We loved kicking back in the living areas, catching up and creating unforgettable memories. With easy beach access just a short walk away, plus great home amenities, this vacation surpassed our expectations, making our stay 5 stars without a doubt. We already booked for next year, and recommend this home to everyone!
William S
Posted: 10/27/2025
Great house
Beautiful modern home with a gorgeous pool. Beach was a short walk. Property management was very responsive to any issues that arose. Would definitely recommend…
Michelle F.
Posted: 10/27/2025
AMI Birthday
This property is stunning. A beautiful location, quiet street and very close to everything you need in terms of grocery, fine dining and or casual needs. Walking distance to the beach without question. The golf cart and bikes are a lovely touch. We had a small group of work friends and family in different days to celebrate my birthday. Wonderful memories. I would for sure stay again!
Jennifer C.
Posted: 10/27/2025
Helpful details
Frequently Asked Questions
The Black Pearl is located in Holmes Beach, Florida.
The Black Pearl accommodates up to 8 guests.
4 Bedrooms and 5 Full, 1 Half Bathrooms.
The listed beach access for The Black Pearl is Near a Beach.
Yes. The property lists Pool (Private).
Yes. The Black Pearl is listed as pet friendly. Review the manager's policies for any pet restrictions or fees.
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