Location
Description
Welcome to Fins Up!
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
Your serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenience, and connection. Soaring ceilings, natural light, and soothing tones create an inviting backdrop for days spent at the beach and evenings gathered by the pool.
Perfect for: couples seeking renewal, small families craving quality time, or travelers looking for calm, connection, and comfort.
Highlights
- Private heated pool with sun shelf, covered seating, and outdoor bar
- 2 bedrooms / 2 bathrooms + queen sleeper sofa (approx. 1,250 sq. ft.)
- Two en-suite bedrooms — ideal for shared comfort and privacy
- Open-concept living area with vaulted ceilings and Smart TV
- Fully equipped kitchen with stainless-steel appliances and quartz countertops
- Washer and dryer in-unit
- Two blocks from the beach and steps from the free island trolley
Interior Spaces
- A space designed for presence — light, calm, and ease.
- The open-concept layout connects the kitchen, dining, and living areas under vaulted ceilings, creating a sense of airiness and flow. Sliding glass doors open to the balcony, welcoming the Florida sunshine and gentle island breeze.
- King Bedroom: Spacious and restful with Smart TV, en-suite bath featuring a walk-in shower, and direct access to a covered deck — perfect for morning coffee or quiet evenings.
- Bunk Room: Full-over-full bunk beds, Smart TV, and en-suite bath with walk-in shower — ideal for kids or guests.
- Living Area: Comfortable sofa (queen sleeper), Smart TV, and open sightlines to the kitchen for easy togetherness.
Subtle coastal décor, crisp finishes, and thoughtful details make this home a relaxing environment that feels as refreshing as a morning swim.
Layout Overview
- Single-level elevated home (approx. 1,250 sq. ft.)
- Two bedrooms, both with en-suite baths
- Open living, dining, and kitchen area
- Balcony overlooking pool and tropical landscaping
- Ground-level outdoor living area with private pool and bar seating
This thoughtful layout provides privacy when desired and connection when it matters most.
Outdoor Living
- Your own private island sanctuary awaits below.
- Heated private pool with sun shelf and surrounding lounge area
- Covered patio with outdoor bar, TV, and dining space for shaded relaxation
- Outdoor shower for a refreshing rinse after the beach
- Gas grill and dining area for easy poolside meals
- Tropical landscaping that adds to the sense of peace and seclusion
It’s a place to pause, breathe, and reconnect — whether lounging in the shade or sharing laughter under the palm trees.
Kitchen & Dining
A bright and functional kitchen sits at the heart of the home, bringing everyone together for meals, conversation, and moments that linger.
- Stainless-steel appliances: stove, oven, dishwasher, microwave, refrigerator with ice maker
- 12-cup coffee maker, blender, toaster, and full kitchenware
- Solid wood cabinets and quartz countertops
- Dining table with seating for four + bar seating for two
From morning smoothies to seafood dinners, the space is designed to make cooking easy and connection effortless.
Additional Amenities
- Central A/C & heat
- Smart TVs and high-speed Wi-Fi
- Linens, towels, and starter amenities provided
- Hair dryer, iron & ironing board
- Washer and dryer for guest use
- Beach gear credit through VayKLife Gear (chairs, umbrella, bikes, etc.) delivered before arrival
Once Upon A Beach provides trusted, hands-on local support — ensuring your stay is seamless, relaxed, and memorable.
Parking
- Two-car garage and space for two additional vehicles in the driveway
- No street or overnight parking permitted
At Fins Up, mornings start with sunlight and the sound of palms, and end with a quiet swim beneath the stars.
It’s where time slows, balance returns, and every day feels like a breath of fresh air.
Write Your Vacation Story.
Policies
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 / No Pets
- Primary guest must be 25+ and remain on-site for the duration of the stay
- Quiet Hours: 10 PM – 8 AM — please respect our island community.
- Minimum Stay: Requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
- Pool & Spa: Heated to 82–85°F year-round; spa, if available, operates as part of the pool system.
- Beach Gear: Rental credit included; some items may be onsite 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 compliance; not facing private areas.
- Accessibility: Home is not wheelchair accessible; stairs required.
City of Holmes Beach Vacation Rental License: VRC18-000018
Max Occupancy: 6 Guests | Max Vehicles: 3
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
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
Your serene island retreat where simplicity meets comfort. Tucked within the heart of Holmes Beach and just two blocks from the sand, this coastal home balances calm, convenience, and connection. Soaring ceilings, natural light, and soothing tones create an inviting backdrop for days spent at the beach and evenings gathered by the pool.
Perfect for: couples seeking renewal, small families craving quality time, or travelers looking for calm, connection, and comfort.
Highlights
- Private heated pool with sun shelf, covered seating, and outdoor bar
- 2 bedrooms / 2 bathrooms + queen sleeper sofa (approx. 1,250 sq. ft.)
- Two en-suite bedrooms — ideal for shared comfort and privacy
- Open-concept living area with vaulted ceilings and Smart TV
- Fully equipped kitchen with stainless-steel appliances and quartz countertops
- Washer and dryer in-unit
- Two blocks from the beach and steps from the free island trolley
Interior Spaces
- A space designed for presence — light, calm, and ease.
- The open-concept layout connects the kitchen, dining, and living areas under vaulted ceilings, creating a sense of airiness and flow. Sliding glass doors open to the balcony, welcoming the Florida sunshine and gentle island breeze.
- King Bedroom: Spacious and restful with Smart TV, en-suite bath featuring a walk-in shower, and direct access to a covered deck — perfect for morning coffee or quiet evenings.
- Bunk Room: Full-over-full bunk beds, Smart TV, and en-suite bath with walk-in shower — ideal for kids or guests.
- Living Area: Comfortable sofa (queen sleeper), Smart TV, and open sightlines to the kitchen for easy togetherness.
Subtle coastal décor, crisp finishes, and thoughtful details make this home a relaxing environment that feels as refreshing as a morning swim.
Layout Overview
- Single-level elevated home (approx. 1,250 sq. ft.)
- Two bedrooms, both with en-suite baths
- Open living, dining, and kitchen area
- Balcony overlooking pool and tropical landscaping
- Ground-level outdoor living area with private pool and bar seating
This thoughtful layout provides privacy when desired and connection when it matters most.
Outdoor Living
- Your own private island sanctuary awaits below.
- Heated private pool with sun shelf and surrounding lounge area
- Covered patio with outdoor bar, TV, and dining space for shaded relaxation
- Outdoor shower for a refreshing rinse after the beach
- Gas grill and dining area for easy poolside meals
- Tropical landscaping that adds to the sense of peace and seclusion
It’s a place to pause, breathe, and reconnect — whether lounging in the shade or sharing laughter under the palm trees.
Kitchen & Dining
A bright and functional kitchen sits at the heart of the home, bringing everyone together for meals, conversation, and moments that linger.
- Stainless-steel appliances: stove, oven, dishwasher, microwave, refrigerator with ice maker
- 12-cup coffee maker, blender, toaster, and full kitchenware
- Solid wood cabinets and quartz countertops
- Dining table with seating for four + bar seating for two
From morning smoothies to seafood dinners, the space is designed to make cooking easy and connection effortless.
Additional Amenities
- Central A/C & heat
- Smart TVs and high-speed Wi-Fi
- Linens, towels, and starter amenities provided
- Hair dryer, iron & ironing board
- Washer and dryer for guest use
- Beach gear credit through VayKLife Gear (chairs, umbrella, bikes, etc.) delivered before arrival
Once Upon A Beach provides trusted, hands-on local support — ensuring your stay is seamless, relaxed, and memorable.
Parking
- Two-car garage and space for two additional vehicles in the driveway
- No street or overnight parking permitted
At Fins Up, mornings start with sunlight and the sound of palms, and end with a quiet swim beneath the stars.
It’s where time slows, balance returns, and every day feels like a breath of fresh air.
Write Your Vacation Story.
Policies
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 / No Pets
- Primary guest must be 25+ and remain on-site for the duration of the stay
- Quiet Hours: 10 PM – 8 AM — please respect our island community.
- Minimum Stay: Requirements vary by city ordinance and are often 7 nights. Please contact our office with any questions.
- Pool & Spa: Heated to 82–85°F year-round; spa, if available, operates as part of the pool system.
- Beach Gear: Rental credit included; some items may be onsite 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 compliance; not facing private areas.
- Accessibility: Home is not wheelchair accessible; stairs required.
City of Holmes Beach Vacation Rental License: VRC18-000018
Max Occupancy: 6 Guests | Max Vehicles: 3
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
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Amenities 146
Accommodations
- Wifi
Amenities
- Bed Linens
- Cable/satellite TV
- Dryer
- Garage
- Hair Dryer
- Hangers
- Heating
- Internet
- Internet Access
- Iron
- Iron Board
- Linens
- Linens provided
- Living Room
- Parking
- Private Entrance
- Self Check-In
- Smartlock
- Telephone
- Towels
- Towels provided
- TV
- Washer
Attractions
- Bay
- Botanical Garden
- Health Beauty Spa
- Marina
- Museums
- Playground
- Theme Parks
- Water Parks
- Zoo
Car
- Not Necessary
- Recommended
Changeover/Arrival Day
- 24Hr Check-In
Cleanliness
- 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
- Emergency Exit Route
- Emergency Fire Contact
- Emergency Medical Contact
- Emergency Police Contact
Entertainment
- Laptop Friendly
- Satellite or Cable
- Television
Kitchen and Dining
- BBQ
- Coffee Maker
- Cooking Basics
- Dining Area
- Dining table
- Dishes Utensils
- Dishwasher
- Freezer
- Fridge
- Kettle
- Kitchen
- Microwave
- Oven
- Refrigerator
- Room
- Spices
- Stove
- Toaster
- Wine glasses
Leisure
- Antiquing
- Bird Watching
- Boating
- Eco Tourism
- Horse riding nearby
- Horseback Riding
- Miniature Golf
- Shopping
- Water Sports
- Wildlife Viewing
Local Features
- ATM Bank
- Fitness Center
- Groceries
- Hospital
- Laundromat
Location Types
- Beach
- Beach or lakeside relaxation
- Near Ocean
Outdoor
- Balcony
- Beach Access
- Deck Patio Uncovered
- Garden Or Backyard
- Grill
- Lanai Gazebo Covered
- Outdoor seating
- Patio
- Patio Or Balcony
- Private yard
Pool/Spa
- Heated outdoor pool
- Heated Outdoor Pool Private
- Heated Pool
- Private Pool
Safety Features
- Carbon Monoxide Detector
- Deadbolt Lock
- Fire Extinguisher
- First Aid Kit
- Outdoor Lighting
- Smoke Detector
Sports and Adventure
- 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
- Roller Blading
- Sailing
- Scuba or Snorkeling
- Skiing Water
- Snorkeling
- Snorkeling / Diving
- Surfing
- Swimming
- Tennis
- Tennis courts nearby
- Tubing Water
- Watersports nearby
- Wind Surfing
Suitability
- Air Conditioning
- Ceiling fans
- Central heating
- Children Welcome
- Decked area
- Free Parking
- Hot Water
- Long Term Stays Allowed
- Minimum Age Limit
- Pets Not Allowed
- Private Living Room
- Smoking Not Allowed
Themes
- Family
- Romantic
Reviews
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Have a question? Customer Questions & Answers
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?"
Hello Can you please tell me if we have the whole house to ourselves or is it a split and another family shares the amenities and pool.
Answer:
This home is technically a duplex because it shares one wall with the next door building. However, all aspects of the home are private for your use only including entry, backyard, pool, etc.
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