Entire home
Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach
Holiday home in Holmes Beach with private pool and kitchen
Photo gallery for Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach





Reviews
10 out of 10
Exceptional
2 bedrooms2+ bathroomsSleeps 6116.1 sq m
Popular amenities
Explore the area

- Place, Manatee Public Beach
- Place, Bean Point Beach
- Place, Anna Maria Beach
- Airport, Sarasota, FL (SRQ-Sarasota-Bradenton Intl.)
Rooms & beds
2 bedrooms (sleeps 6)
Common Space
1 Double Sofa Bed
Master
1 King Bed
Second
1 Single Bunk Bed
2 bathrooms, 1 half bathroom
Half Bathroom 3
Toilet
Master
Toilet · Shower only
Second
Toilet · Shower only
Spaces
Deck or patio
Kitchen
Balcony
Separate dining area
Dining area
About this property
Fins Up – AMI Cozy Island Retreat w/ Private Pool & 4-Min Walk To Beach
Welcome to Fins Up!
On Anna Maria Island (Holmes Beach, FL)
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
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
NO SMOKING. NO PETS.
Booking & Fee Policy
Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.
Optional Services (subject to approval)
Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.
Reservations & Guest Requirements
Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.
Quiet Hours
10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.
Cleaning & Linens
Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.
Golf Cart Rentals
Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.
Pool & Spa
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.
Property Security
Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.
Payments & Cancellation Policy
Policies updated October 6, 2025 — see full Terms & Conditions for details.
Payment Schedule
Deposit
- Reservations up to 20 days: 50% of total amount due at time of booking.
Remaining Balance
- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.
Cancellation Policy
For Reservations of 20 Days or Less
- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.
- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.
- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.
- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.
Travel Insurance
CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.
Additional Terms
No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.
City of Holmes Beach Vacation Rental License: VRC18-000026
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)
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
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
NO SMOKING. NO PETS.
Booking & Fee Policy
Include all guests and pets in your reservation request for accurate pricing. Additional fees apply for extra occupancy (over 2 guests per bedroom) or undeclared pets.
Optional Services (subject to approval)
Early check-in/late departure, elevator access, and mid-stay cleaning for stays of 28+ days. Fees for approved add-ons are collected after booking.
Reservations & Guest Requirements
Most stays are 7 nights, Saturday–Saturday, though flexible dates may be available outside peak/holiday weeks—confirm before booking, as changes are not always possible afterward. Guests must be 25+, provide valid ID, and remain for the full stay. Standard occupancy is 2 per bedroom; extra guests are $25/person/night up to the maximum allowed.
Quiet Hours
10 PM–8 AM. Maintain reasonable noise at all times to respect neighbors; excessive noise is not permitted.
Cleaning & Linens
Home is professionally cleaned and sanitized between stays. Starter amenities provided; daily service available for a fee. Stays of 28+ days require a mid-stay clean. Linens/towels are commercially laundered through our Professional Linen Program; no extra sets stored onsite.
Golf Cart Rentals
Explore the island with ease! After booking, reserve a golf cart through our sister company, Once Upon A Beach Carts, and enjoy an exclusive discount available only to our vacation rental guests.
Pool & Spa
Pool heated year-round to 82–85°F; heating may be affected by cooler weather. Heaters/filters off during quiet hours (10 PM–8 AM). Spa, if available, is part of the pool, seasonal, not a commercial hot tub, and may be unavailable in summer. Guests may not adjust equipment; violations may result in fines or damages.
Property Security
Exterior cameras may monitor entries, driveways, pool equipment, and backyard access for security, deliveries, and occupancy compliance. Cameras do not face private areas.
Payments & Cancellation Policy
Policies updated October 6, 2025 — see full Terms & Conditions for details.
Payment Schedule
Deposit
- Reservations up to 20 days: 50% of total amount due at time of booking.
Remaining Balance
- Reservations up to 20 days: Remaining 50% due 30 days prior to check-in.
Cancellation Policy
For Reservations of 20 Days or Less
- More than 30 days before arrival: Full refund of deposit (including taxes) minus non-refundable booking administration fee.
- 14–29 days before arrival: Refund of 50% of total rental, fees, and taxes, minus non-refundable booking administration fee.
- Less than 14 days before arrival: Refunds only for base rental rate, fees, and taxes for nights we are able to rebook, minus non-refundable booking administration fee.
- Please note: While we make every effort to rebook, we cannot guarantee the same rate or number of nights. For any nights that cannot be re-rented, as well as for non-arrivals, late arrivals, early departures, or alterations resulting in lost revenue, no refunds or price adjustments will be made.
Travel Insurance
CSA Travel Insurance is available to U.S. guests (except NY and HI residents) and is strongly encouraged to protect your trip from unforeseen events. No refunds are given for COVID-19, weather, or beach conditions outside our cancellation policy. Hurricane season runs June 1–Nov 30; insurance can safeguard your plans. In the event of a mandatory evacuation, home unavailability, or government order halting vacation rentals, guests receive a full refund of base rate, applicable fees (minus booking fee), and taxes.
Additional Terms
No refunds for events beyond our control (weather, red tide, travel issues, etc.). Cancellation requests must be submitted in writing by the registered guest—phone/text not accepted.
City of Holmes Beach Vacation Rental License: VRC18-000026
Max Occupancy: 6 Guests | Max Vehicles: 3
Information deemed reliable but not guaranteed; subject to change or withdrawal without notice.
Add dates for prices
Amenities
Pool
Kitchen
Washing machine
Dryer
Free WiFi
Air conditioning
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House Rules
Check in after 4:00 PM
Minimum age to rent: 25
Check out before 10:00 AM
Children
Children allowed: ages 0–17
Events
No events allowed
Pets
No pets allowed
Smoking
Smoking is not permitted
Check-out instructions
The host requires you to complete the following before checking out:
Load and start the dishwasher
Strip any used beds, gather used towels and store extra beds
Remove personal items, remove leftover food and drinks and take out the rubbish
Turn off the lights, lock the doors and return the keys
VayKLife Beach Gear: Please ensure that all rented items from VayKLife are returned to their original delivery location outdoors. Do not pull items inside.
Failure to complete these may result in a negative review from the host.
Important information
You need to know
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, a first aid kit and a deadlock
About the area
Holmes Beach
Located in Holmes Beach, this holiday home is near theme parks and near the beach. The area's natural beauty can be seen at Bean Point Beach and Anna Maria Beach. Looking to enjoy an event or a game while in town? See what's happening at LECOM Park or IMG Bollettieri Tennis Academy. Make sure you get close to the area's animals with activities such as game walks and birdwatching.

Holmes Beach, FL
What's nearby
- Bradenton Beach - 5 min walk - 0.4 km
- Holmes Beach Beaches - 19 min walk - 1.6 km
- Manatee Public Beach - 4 min drive - 2.1 km
- Bean Point Beach - 6 min drive - 3.8 km
- Anna Maria Beach - 8 min drive - 4.5 km
Getting around
Restaurants
- The Ugly Grouper - 9 min walk
- The Sandbar Restaurant - 4 min drive
- Anna Maria Island Beach Cafe - 4 min drive
- Skinny's Place - 4 min drive
- Hurricane Hanks - 12 min walk
Frequently asked questions
About the host
Hosted by Once Upon a Beach Vacation Rentals
A world-class island getaway deserves a premier vacation rental experience. At Once Upon A Beach, we invite you to immerse yourself in laid-back luxury, where every detail is designed to make your stay unforgettable. From the moment you book until the day you depart, our local, dedicated team delivers exceptional service, ensuring your vacation is seamless, stress-free, and unforgettable.
Whether you're seeking a romantic retreat for two in a charming beach-chic cottage or gathering the whole family in a sprawling luxury home, you'll arrive to find a meticulously maintained property with unique, thoughtful amenities and concierge-style insider tips to help you live like a local. Each home is just steps from Anna Maria Island's sugar-soft white sand and the sparkling, gin-clear waters that make our slice of paradise famous.
As a boutique luxury vacation rental and property management company, Once Upon A Beach offers an intimate, personalized experience rooted in five-star care and meticulous attention to detail. We specialize in creating the perfect balance of comfort, style, and authentic island charm in one of the most picturesque beach towns in the world—the place we proudly call home.
Write the next chapter of your vacation story with us, and create cherished memories on Anna Maria Island that will last a lifetime.
Whether you're seeking a romantic retreat for two in a charming beach-chic cottage or gathering the whole family in a sprawling luxury home, you'll arrive to find a meticulously maintained property with unique, thoughtful amenities and concierge-style insider tips to help you live like a local. Each home is just steps from Anna Maria Island's sugar-soft white sand and the sparkling, gin-clear waters that make our slice of paradise famous.
As a boutique luxury vacation rental and property management company, Once Upon A Beach offers an intimate, personalized experience rooted in five-star care and meticulous attention to detail. We specialize in creating the perfect balance of comfort, style, and authentic island charm in one of the most picturesque beach towns in the world—the place we proudly call home.
Write the next chapter of your vacation story with us, and create cherished memories on Anna Maria Island that will last a lifetime.
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