We offer short-term and mid-term stays. This listing has amazing month-to-month rates, weekly stays, month-long stays…..Ask us for details!
Listing Description of you dream Vacation Your Way vacation home:
️ Bedrooms
Bedroom 1: King, TV, closet, dresser
️ Bedroom 2: Queen, TV, dresser, closet
️ Bedroom 3: Two twin beds – highchair in closet, ideal for kids
Fresh, sanitized, clean bed linens and towels are provided
Bathrooms
Bathroom 1: sink, toilet tub and shower
Bathroom 2: sink, toilet and shower
Living Room
Spacious and Bright Living Room – Open-concept layout w/ Smart TV and cozy seating
️ Sun Room/Office Area
office desk – great for productivity
Area
Table and Chairs to relax in sun room
Kitchen
️Fully Stocked Kitchen – Stainless steel appliances, cookware, and coffee bar
Refrigerator/Freezer
Stove/Oven
Microwave and Toaster
Espresso + K-Cup coffee makers for your morning fix
Dishwasher
Cookware and Utensils
️ Outdoor Paradise – Exclusive to Vacation Your Way Guests
Private Swim Spa – Relaxation, fitness, and family fun
Luxury Daybeds and Chaise Lounges – Perfect for sunbathing and unwinding
Outdoor Kitchen and Dining Area – Create unforgettable alfresco meals; propane grill, small refrigerator, counterspace
Tiki Bar and Fire Table – Enjoy drinks and cozy evenings under the stars
Fenced Backyard – A private sanctuary for your retreat
Cornhole game
Beautiful new shed with bikes, beach chairs, and beach umbrella to borrow
️ Amenities and Extras
Sparkling Clean – We take pride in providing a sanitized, comfortable space!
Effortless Arrival – PULSAR Smart Home lock
Dedicated Workspace – Stay connected with high-speed Wi-Fi
Iron and ironing board
Starter supplies provided: paper towels, toilet paper, K-Cups, sugar, creamer, toiletries, dish soap, and laundry detergent.
Pet-Friendly Upon Request – Ask us before booking!
Location Highlights
1.5 miles – Gulf Coast Beaches Crystal-clear waters and pristine sands
1 mile – Waterside Shops ️ Fine dining and high-end shopping
1 mile – 5th Avenue South Art galleries, night life, and entertainment
3 miles – Naples Botanical Garden Stunning seasonal exhibits and lush landscapes
Good to Know
Check-in: 4 PM | Check-out: 10 AM
Parking – Space for 1-2 cars in the designated parking lot.
Minimum Renter Age – 20 years old.
No Smoking (use ashtrays if you smoke outside)
No Parties, no visitors without permission from host
️ Pool access is weather-dependent (acts of God not covered)
No water balloons, or foam toys
Pool care is needed during your stay. Please expect to skim/brush, empty filter basket and run hose/water to keep the pool full. Many Thanks!
FL Bugs Disclaimer: We use professional pest control, but minor pest activity may occur between cleanings
Iguanas are our best pest control. They will be hanging around the storage swim spa and backyard! Majestic creatures! Not dangerous- just surprising!
When booking...please provide the correct # of adults and children to get an accurate price. We employ the common practice of charging a guest fee per person to offset the utilities of the home.
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Unique Benefits
Unique Benefits of Staying at 1224 Hilltop Dr, Naples, FL
Prime Location
Centrally located, offering quick access to Naples’ top attractions like the Naples Pier, Fifth Avenue South, and the beach.
Close to everyday conveniences such as grocery stores, coffee shops, and local dining options.
Relaxed Residential Setting
Nestled in a peaceful neighborhood with no HOA restrictions, providing more flexibility and privacy for guests.
Proximity to Beaches
Just minutes from Naples' stunning Gulf Coast beaches, perfect for sunbathing, swimming, or paddleboarding.
Family-Friendly Environment
Safe, quiet streets ideal for families with children or pets.
Nearby parks and playgrounds for outdoor fun.
Outdoor Living Potential
Potential for a private backyard space to relax, dine al fresco, or enjoy Naples' warm weather.
Access to Unique Naples Experiences
Close to local gems like the Naples Zoo, Naples Botanical Garden, and the Gordon River Greenway.
Easy access to cultural highlights like Artis—Naples and The Baker Museum.
Blend of Tranquility and Convenience
Offers a peaceful retreat without sacrificing proximity to Naples’ vibrant dining, shopping, and entertainment districts.
This property offers the perfect combination of comfort, convenience, and a quintessential Naples experience!
Why Kids Love It
Kids are sure to love 1224 Hilltop Dr in Naples, FL, for several reasons:
1. Close to Fun Attractions
Naples Zoo: A short drive away, offering up-close animal encounters and family-friendly activities.
Gordon River Greenway: Perfect for biking, walking, and spotting wildlife in a natural setting.
Beaches: Quick access to kid-friendly beaches like Lowdermilk Park with shallow waters and a playground.
2. Outdoor Play Opportunities
The area features quiet, residential streets where kids can ride bikes or play outside.
Nearby parks like Fleischmann Park offer playgrounds, sports courts, and green spaces for running around.
3. Family-Friendly Neighborhood
The community is welcoming and residential, making it ideal for families with young children.
4. Educational Fun
Naples Botanical Garden offers engaging kids' programs and fun opportunities to explore nature.
The Children’s Museum of Naples (CMON) is nearby, where kids can enjoy hands-on learning exhibits.
5. Room to Grow
The property itself has a backyard perfect for playing games, hosting BBQs, and swimming in swim spa
This home’s location and its proximity to so many kid-friendly activities make it a place kids won’t want to leave!
1224 Hilltop Dr in Naples, FL, is conveniently located near several notable attractions: (a short drive- not walking...)
Naples Botanical Garden: A 170-acre garden showcasing diverse plant species and offering educational programs for all ages.
Gordon River Greenway: A nearly 2-mile trail system along the Gordon River, ideal for walking, cycling, and nature observation.
Naples Zoo: A family-friendly zoo featuring a variety of animal exhibits and interactive experiences.
Naples Pier: A historic 1,000-foot pier perfect for fishing, dolphin watching, and enjoying sunsets.
Fifth Avenue South: A vibrant district offering dining, shopping, and entertainment options.
Third Street South: Known for its charming atmosphere, upscale shops, and restaurants.
Naples Historical Society's Historic Palm Cottage: The oldest house in Naples, offering guided tours and insights into the area's history.
Delnor-Wiggins Pass State Park: A barrier island park with beaches, boating, and wildlife viewing opportunities.
Clam Pass Park: Features a scenic boardwalk through mangroves leading to a tranquil beach.
Artis—Naples: A cultural complex housing the Naples Philharmonic and The Baker Museum.
These attractions provide a range of activities, from nature exploration to cultural experiences, all within a short distance of 1224 Hilltop Dr.
When I’m in Naples, FL, these are my go-to spots for an amazing meal. For beachfront dining, nothing beats The Turtle Club—their fresh seafood and ocean views are incredible. When I’m in the mood for Italian, Osteria Tulia is a must with its rustic charm and delicious, creative dishes. For a special night out, I love Sea Salt—their modern menu and wine selection never disappoint. If I’m keeping it casual, Brooks Burgers serves the best gourmet burgers around, and Pinchers is my spot for authentic Gulf Coast flavors. And no visit to Naples is complete without dessert at Kilwins—their handmade chocolates and ice cream are the perfect treat.
Here’s the inside scoop on Naples, FL, that locals love to keep under wraps:
Happy Hour Gems: Check out USS Nemo for discounted seafood dishes during happy hour. For cocktails with a view, Baleen at LaPlaya Beach Resort has a lesser-known sunset happy hour.
Best Beach Spots: Locals favor Lowdermilk Park for its peaceful vibe and amenities or Clam Pass Park, which requires a charming tram ride through mangroves to reach the beach.
Coffee and Breakfast: Skip the chains and grab a coffee at Kunjani, a cozy café with a mission to give back, or try The Brick Coffee & Bar for breakfast with a creative twist.
Hidden Nature Trails: Walk the Gordon River Greenway for a quiet escape in nature, or visit Naples Preserve to spot gopher tortoises.
Fresh Finds: Hit the Third Street Farmers’ Market on Saturdays for fresh produce, local bites, and live music.
Quiet Fine Dining: Locals rave about The French Brasserie Rustique, a hidden gem off 5th Avenue with a cozy, intimate atmosphere.
Free Sunset Fun: Head to the Naples Pier for dolphin watching during sunset—no need to splurge on a boat tour!
Insider Parking Tip: If you're heading downtown, park in the free parking garage on 8th Street—it’s close to all the action without the hassle.
Enjoy Naples like a true local!
BBQ Area
Carbon Monoxide Detector
Cooking Basics
Marina
Essentials
Living Room
Hot Water
Luggage Dropoff Allowed
Private Entrance
Shampoo
Single Level Home
Smoke Detector
Shopping
Near Ocean
Grill (charcoal)
Wireless Internet
Fenced Pool
Free wifi
Smart TV
Kitchen Island
Dining table
Water Recreation Location
Internet
PET ALLOWED
Games/Puzzels
Private Living Room
Family
Historic
Romantic
Tourist Attractions
Museums
Zoo
Car Recommended
Extra Pillows & Blankets
Fire Extinguisher
First Aid Kit
Garden or Backyard
Jacuzzi
Shower Chair
Spices
Bicycle
Lanai Gazebo Covered
Spa
Fenced Yard
Printer
Desk
Conditioner
Pet Friendly
No Booking or Service Fees
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| Rate Period | Nightly | Weekend Night | Weekly | Monthly | Min Stay |
|---|---|---|---|---|---|
Dec 04 - Dec 05 2025 | $159 | 2 nights | |||
Dec 05 - Dec 11 2025 | $153 | 2 nights | |||
Dec 12 - Dec 13 2025 | $173 | 2 nights | |||
Dec 13 - Dec 14 2025 | $177 | 2 nights | |||
Dec 14 - Dec 19 2025 | $153 | 2 nights |
Fees:
Notes:
FL State Accommodation Tax: 6%
Collier FL Accommodation TAX: 5%
Collier FL County Sales and Use Tax: 1%
Last updated on December 04, 2025
Angeline M.This place was such a relaxing and fun place to be!
This place was such a relaxing and fun place to be. The backyard was definitely the highlight, with the SwimSpa, tiki bar, fire pit, and even an outdoor kitchen, we spent most of our time outside. Inside, the house was super clean, comfortable, and had everything we needed. The location was great too, quiet neighborhood but still close to beaches, shops, and restaurants. Overall, it felt like a true getaway, and I’d 100% come back again.
Stayed: February 2025 Submitted: August 06, 2025
Wendy S.Great Naples rental!
We needed a place to stay in Naples that would accommodate our cats. This was a great find at the last minute! The agent Cara is super responsive and helpful and accommodating! From the time we found her and throughout our rental and beyond. Since I left something there, I have still been in touch with her several times, trying to figure out how to retrieve it. Again, she is super helpful.The Bungalow is newly renovated and clean, and “modern“. The kitchen has pretty much everything you would need.It is small but was perfect for the two of us and our two cats.It’s a phenomenal location for Naples. Close to everything! Also, it’s a nice walking area in the neighborhood if you enjoy that.The things that I pointed out to Cara that needed attention were quickly addressed, and I assume taken care of after we left. The things that needed attention right then were taken care of right away!
Stayed: March 2025 Submitted: March 31, 2025
Erik M.Location location location!
This house has everything you want in Naples. Amazing private backyard with oversized swim spa and less than 2 miles to the beach. The beds were comfortable and perfect distance to shopping on 5th avenue. Will definitely be back.
Stayed: November 2024 Submitted: December 27, 2024
Host response
"Thank you, Erik! What a joy to host you! I agree we worked very hard to provide a clean and sanitized home for you with comfortable beds! So much better than a hotel! (Small, beds are inconsistent & you never know who will be yelling outside your door!). I also love this amazing location- close to beaches and awesome shopping! We look forward to hosting you again soon! VYW"
Jay B.Reasonably Priced Comfort
I had an amazing experience renting the is property! It he location was perfect, the amenities were tons-notch and the host was responsive and accommodating. Highly recommend for anyone looking for a comfortable stay.
Stayed: November 2024 Submitted: December 09, 2024
Host response
"Jay, It was a joy to have you as a guest at our fantastic Naples, FL beach house! I'm so happy you loved taking laps in our Swim Spa every morning & dips in the Hot Tub each evening - what an oasis! We look forward to hosting you again soon! Blessings, Kara"
Member since 2024