5595 Gregg Street
- 4 Beds |
- 5.5 Baths |
- 10 Guests
5595 Gregg Street
Step into elevated coastal living in this exceptional 4-bedroom luxury residence in the storied enclave of American Beach, hosted by Stay Better Vacations. Designed for relaxation and entertaining, this home blends refined interiors with expansive outdoor living and panoramic island views — topped by a rooftop terrace with 360-degree views just 200 feet from the Atlantic.
IMPORTANT: For the security of the property and our guests, this home is equipped with exterior security cameras and is actively monitored. Cameras are located at the garage, on the lamp post at street level, and along the sides and rear of the home, providing video coverage of the entire exterior perimeter. Any unauthorized guests, parties, events, or pets may result in immediate removal from the property without refund.
Welcome to 5595 Gregg St, set in the historic American Beach neighborhood. This four-bedroom, five-and-a-half-bathroom luxury home rises four levels — with an elevator connecting every one of them — and tops out at a rooftop terrace with 360-degree views and the kind of sky you'll want to wake up early for. The Atlantic is right there. Burney Park's public beach access is approximately 200 feet away. Some vacations give you a place to sleep. This one gives you a whole different way to experience the island.
Rooftop Living at Its Finest. The crown jewel of the home is the rooftop terrace, offering sweeping 360-degree views—from the northern tip of Amelia Island to its southern shores. This space is built for unforgettable moments, complete with:
Sophisticated Coastal Comfort
Every detail of this home was curated for comfort and style. Sleeping accommodations include:
American Beach holds a unique and meaningful place in Florida’s history. Established in 1935 during segregation, it was one of the few beaches in the Southeast open to African Americans. It quickly became a cultural hub—often referred to as the place for “recreation and relaxation without humiliation.” Today, it retains that rich heritage while offering a quieter, more natural stretch of coastline compared to other parts of Amelia Island.
Location & Lifestyle
Tucked away from the crowds yet close enough to enjoy the island’s dining, golf, and charm, this home offers the best of both worlds—privacy, history, and luxury in one setting. This is more than a vacation rental—it’s a destination property designed for guests who expect space, quality, and a memorable coastal experience. Situated between the Ritz Carlton and Omni Amelia Island for quick access to your destination weddings, conferences, and events.
Details to Know
BUT WAIT, THERE'S MORE! The digital guestbook you'll receive after booking provides you with DIRECTIONS, ADDRESS, MAPS, PARKING, AMENITIES INCLUDED, A LOCAL AREA GUIDE - with many of our favorites - and much, much more!
IT'S ADVISABLE to purchase travel insurance to safeguard your vacation investment. Additionally, please be aware that we don't offer refunds or rescheduling for bookings impacted by inclement weather, including tropical storms or hurricanes.
--IT'S AN ISLAND THING--
Discover the allure of tranquil Amelia Island, nestled in Northeast Florida and embraced by Southern hospitality. Amelia Island beckons you with pristine beaches to the east, breathtaking marshes to the west, and island charm throughout. Conveniently accessible from Jacksonville International Airport, AI invites you to explore 13 miles of beautiful beaches, abundant native wildlife, meandering walking and biking trails, the historic Fort Clinch State Park, and captivating sunsets.
Embrace your adventurous side with activities like golfing, kayaking, boating, and fishing. Delight your taste buds by exploring culinary treasures to include fresh shrimp & seafood found in locally-owned eateries and fine restaurants. Whether you seek relaxation on the shore or crave indulgence through spa treatments, Amelia Island promises to fulfill your desires.
Welcome to 5595 Gregg St, set in the historic American Beach neighborhood. This four-bedroom, five-and-a-half-bathroom luxury home rises four levels — with an elevator connecting every one of them — and tops out at a rooftop terrace with 360-degree views and the kind of sky you'll want to wake up early for. The Atlantic is right there. Burney Park's public beach access is approximately 200 feet away. Some vacations give you a place to sleep. This one gives you a whole different way to experience the island.
Rooftop Living at Its Finest. The crown jewel of the home is the rooftop terrace, offering sweeping 360-degree views—from the northern tip of Amelia Island to its southern shores. This space is built for unforgettable moments, complete with:
- Two gas grills
- Large-screen TV
- Teak loungers
- Outdoor sectional seating
- Dining table for group meals under the sky
Sophisticated Coastal Comfort
Every detail of this home was curated for comfort and style. Sleeping accommodations include:
- 3 beautifully appointed king bedrooms, one providing an expanded sitting area with a pull-out sofa
- 1 elegant queen bedroom
- Each bedroom showcases luxury bedding, designer furnishings, and spa-inspired ensuite baths, creating a private retreat for every guest.
- Two bedrooms feature private balconies, including the spectacular primary suite where stackable sliding glass doors open fully to reveal direct ocean views from your bed—allowing the sounds of the Atlantic and morning sunrises to become part of your stay.
- Private elevator servicing all levels—from the first floor to the rooftop
- Two washers and two dryers for effortless extended stays
- Outdoor shower—perfect after beach days
American Beach holds a unique and meaningful place in Florida’s history. Established in 1935 during segregation, it was one of the few beaches in the Southeast open to African Americans. It quickly became a cultural hub—often referred to as the place for “recreation and relaxation without humiliation.” Today, it retains that rich heritage while offering a quieter, more natural stretch of coastline compared to other parts of Amelia Island.
Location & Lifestyle
Tucked away from the crowds yet close enough to enjoy the island’s dining, golf, and charm, this home offers the best of both worlds—privacy, history, and luxury in one setting. This is more than a vacation rental—it’s a destination property designed for guests who expect space, quality, and a memorable coastal experience. Situated between the Ritz Carlton and Omni Amelia Island for quick access to your destination weddings, conferences, and events.
Details to Know
- 4 night minimum
- Adults must be 30 years to book
- A deposit of $500 is required, refundable after departure inspection if no issues are reported
- Maximum occupancy is 10
- Parking for 4-6 cars in driveway depending on size - No garage parking
- This property is equipped with exterior security cameras located at the garage and on the lamp post at street level. The exterior of the home is actively monitored for security purposes and to ensure compliance with occupancy, pet, and event policies.
BUT WAIT, THERE'S MORE! The digital guestbook you'll receive after booking provides you with DIRECTIONS, ADDRESS, MAPS, PARKING, AMENITIES INCLUDED, A LOCAL AREA GUIDE - with many of our favorites - and much, much more!
IT'S ADVISABLE to purchase travel insurance to safeguard your vacation investment. Additionally, please be aware that we don't offer refunds or rescheduling for bookings impacted by inclement weather, including tropical storms or hurricanes.
--IT'S AN ISLAND THING--
Discover the allure of tranquil Amelia Island, nestled in Northeast Florida and embraced by Southern hospitality. Amelia Island beckons you with pristine beaches to the east, breathtaking marshes to the west, and island charm throughout. Conveniently accessible from Jacksonville International Airport, AI invites you to explore 13 miles of beautiful beaches, abundant native wildlife, meandering walking and biking trails, the historic Fort Clinch State Park, and captivating sunsets.
Embrace your adventurous side with activities like golfing, kayaking, boating, and fishing. Delight your taste buds by exploring culinary treasures to include fresh shrimp & seafood found in locally-owned eateries and fine restaurants. Whether you seek relaxation on the shore or crave indulgence through spa treatments, Amelia Island promises to fulfill your desires.
Amenities
Safety Features
Fire Extinguisher
Smoke Detector
Deadbolt Lock
Outdoor Lighting
Suitability
Children Welcome
Pets Not Allowed
Long Term Stays Allowed
Filter Options
Oceanview
Neighborhood View
Walk to Beach
Children Allowed
Elevator in Building
Kitchen and Dining
Kitchen
Dining Area
Refrigerator
Coffee Maker
Microwave
Dishwasher
Dishes Utensils
Stove
Toaster
Oven
Fridge
Freezer
Wine glasses
Baking sheet
Dining table
Amenities
Internet
Air Conditioning
Free Wifi
Heating
Washer
Dryer
Parking
Garage
Living Room
Hair Dryer
Iron Board
Linens
Towels
Elevator
Iron
Hangers
Outdoor
Balcony
Accommodations
Dryer
Elevator in the building
Wifi
Sports and Adventure
Deepsea Fishing
Fishing
Jet Skiing
Sailing
Car
Recommended
Local Features
ATM Bank
Groceries
Hospital
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