Welcome to She's Always Right!
On Anna Maria Island (Holmes Beach, FL)
Managed by Once Upon A Beach Vacation Rentals, a locally owned and operated boutique vacation rental agency.
The Space
Where thoughtful design meets island energy, She’s Always Right blends modern artistry, resort-style comfort, and an unbeatable location just steps from the sand. Here, every detail is intentional — from high ceilings and natural light to vibrant finishes that reflect the spirit of Anna Maria Island itself.
Perfect for: design lovers, families who value connection and comfort, and groups celebrating something special.
Highlights
- Prime Holmes Beach location just one block from the Gulf
- 3 king ensuite bedrooms with TVs + 2 additional sleeping areas for up to 11 guests
- 4 full bathrooms with walk-in showers and modern finishes
- Heated private pool and spa surrounded by lush landscaping
- Gourmet kitchen with high-end appliances and large dining table for 10
- Outdoor decks, balconies, and grilling area perfect for entertaining
- Pet friendly with prior approval
Interior
Step inside to discover open-concept living with vaulted ceilings and curated coastal décor that blends artistry and ease. The main living area is filled with natural light, connecting the gourmet kitchen, dining, and living spaces into one inviting flow.
- Living Area: Relax on plush seating while enjoying the large smart TV. Soft colors, organic textures, and vibrant local artwork create a playful yet elegant atmosphere.
- Dining Area: A table for ten invites connection over shared meals, laughter, and long conversations.
- Chef’s Kitchen: Fully equipped with high-end stainless-steel appliances, including a double oven, induction cooktop, and Keurig. The oversized island doubles as a social hub, offering bar seating for four.
From here, sliding doors open to an elevated deck, where morning coffee and evening cocktails are equally at home.
Kitchen & Dining
Designed for both creativity and convenience:
- Stainless steel appliances including induction cooktop and double oven
- Refrigerator with ice maker and water dispenser
- Dishwasher, microwave, blender, and toaster
- 12-cup coffee maker and Keurig for morning rituals
- Fully stocked kitchenware for family meals or chef-inspired nights in
The open dining area flows seamlessly to the living space, so you can cook, connect, and enjoy the rhythm of island life together.
Layout Overview
- Main Level: Open living, kitchen, and dining; two king ensuite bedrooms; and direct deck access.
- Upper Level: Third king suite with private balcony, twin XL bedroom, and open bunk room with triple twin XL bunk.
- Outdoor Level: Heated pool, spa, lounge seating, and shower — framed by tropical palms for added privacy.
This thoughtful layout allows everyone their own space while keeping shared areas central and connected.
Outdoor Living
Outside, a tropical sanctuary awaits. The heated pool and spa are surrounded by lush landscaping, creating a private retreat just steps from the home. Lounge poolside, rinse off in the outdoor shower, or gather on the deck for grilling and sunset cocktails.
An outdoor foot wash keeps sandy toes at bay after a beach walk, and multiple decks offer quiet corners to soak up the salt air. Whether you’re chasing sunshine or shade, every inch of the space has been designed for comfort and connection.
Additional Amenities
- A/C and heat
- Wireless internet and cable television
- Linens, bath towels, and pool towels provided
- Hair dryer, iron, and ironing board
- Washer and dryer
- Beach gear credit included (chairs, umbrella, bikes, etc. — select items before arrival; onsite items not guaranteed)
Parking
- Driveway: 2–3 vehicles
- Garage: 2 additional spaces
Write Your Vacation Story at She’s Always Right — where creativity meets coastal comfort, and every detail inspires connection, laughter, and ease.
Policies updated October 6, 2025 — see full Terms & Conditions for details.
🔗 Cancellation Policy & Trip Insurance
🔗 Terms & Conditions
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.
- No Smoking
- Pets: Welcome with prior approval; maximum of two pets under 65 lbs each.
- Primary guest must be 25+ and remain on-site for the duration of the stay
- Minimum Stay: Requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
- Quiet Hours: 10 PM – 8 AM — please respect our island community
- Pool & Spa: Heated to 82–85°F year-round; temperature may vary with weather. Spa, if present, operates as part of the pool system, not a stand-alone hot tub.
- Beach Gear: A rental credit is included with your stay; select items before arrival for delivery. Some items may be on-site but are not guaranteed.
- Cleaning & Linens: Professionally cleaned between stays with starter supplies provided. Mid-stay cleans required for stays over 28 days.
- Golf Carts: Reserve through Once Upon A Beach Carts for an exclusive guest discount.
- Security: Exterior cameras monitor entry points and equipment for safety and occupancy compliance. Cameras do not face private areas.
- Accessibility: Home is not wheelchair accessible; stairs required.
City of Holmes Beach Vacation Rental License: VRC18-000006
Max Occupancy: 11 Guests | Max Vehicles: 4
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
- Wifi
- Bed Linens
- Cable/satellite TV
- Dryer
- Hair Dryer
- Hangers
- Heating
- Internet
- Internet Access
- Iron
- Iron Board
- Linens
- Linens provided
- Living Room
- Parking
- Private Entrance
- Self Check-In
- Smartlock
- Towels
- Towels provided
- TV
- Washer
- Bay
- Botanical Garden
- Health Beauty Spa
- Marina
- Museums
- Playground
- Theme Parks
- Water Parks
- Zoo
- Not Necessary
- Recommended
- 24Hr Check-In
- All towels and bedding washed in hot water that's at least 60ºC
- Cleaning Disinfection
- Enhanced Cleaning Practices
- High-touch surfaces cleaned with disinfectant
- Self Check In / Check Out
- Emergency Exit Route
- Emergency Fire Contact
- Emergency Medical Contact
- Emergency Police Contact
- Laptop Friendly
- Satellite or Cable
- Television
- BBQ
- Coffee Maker
- Cooking Basics
- Dining Area
- Dining table
- Dishes Utensils
- Dishwasher
- Freezer
- Fridge
- Kitchen
- Microwave
- Oven
- Refrigerator
- Room
- Spices
- Stove
- Toaster
- Wine glasses
- Antiquing
- Bird Watching
- Boating
- Eco Tourism
- Horse riding nearby
- Horseback Riding
- Miniature Golf
- Shopping
- Water Sports
- Wildlife Viewing
- ATM Bank
- Fitness Center
- Groceries
- Hospital
- Laundromat
- Beach
- Beach or lakeside relaxation
- Near Ocean
- Balcony
- Balcony/Terrace
- Deck Patio Uncovered
- Garden Or Backyard
- Grill
- Outdoor seating
- Patio
- Patio Or Balcony
- Private yard
- Heated outdoor pool
- Heated Outdoor Pool Private
- Heated Pool
- Jacuzzi
- Jacuzzi/hot tub
- Private Pool
- Spa
- Carbon Monoxide Detector
- Deadbolt Lock
- Fire Extinguisher
- First Aid Kit
- Outdoor Lighting
- Smoke Detector
- Basketball Court
- Deepsea Fishing
- Fishing
- Fishing Bay
- Fishing Fly
- Fishing Freshwater
- Fishing nearby
- Fishing Surf
- Golf
- Golf course within 30 min drive
- Jet Skiing
- Kayaking
- Parasailing
- Pier Fishing
- Sailing
- Scuba or Snorkeling
- Skiing Water
- Snorkeling
- Snorkeling / Diving
- Surfing
- Swimming
- Tennis
- Tennis courts nearby
- Tubing Water
- Watersports nearby
- Wind Surfing
- Air Conditioning
- Ceiling fans
- Central heating
- Children Welcome
- Decked area
- Free Parking
- Hot Water
- Long Term Stays Allowed
- Minimum Age Limit
- Pets allowed
- Pets Considered
- Private Living Room
- Smoking Not Allowed
- Family
- Luxury
- Romantic
Want to know specifics? Ask anything about this specific property that you would like to know...
Example: "Is the balcony screened in?" or "Is there a toaster oven?"