Tropical Oaks Estate - 3.8 Acres • 40' Pool + Spa

Naples, Florida
$1047 avg/night
Minimum Stay 1 Nights
Bed 4

Bed

Bath 3

Bath

Home Private Vacation Home

Property Type

Sleep 10

Max Sleeps

Night 1 nights

Min Stay

Welcome to Tropical Oaks Estate — a fully renovated mid-century boho retreat where Naples luxury comes with a little more breathing room.



Set on 3.8 private acres with approximately 300 feet of canal frontage and so central to everything in Naples. This 4-bedroom estate feels worlds away from a typical neighborhood rental, yet you're only about 5 miles from the Gulf and within easy reach of Fifth Avenue South, Third Street South, restaurants, golf and everything Naplesis known for.



The real showstopper A 40-foot saltwater pool and spa surrounded by more than 2,000 sq. ft. of screened marble-decked outdoor living space.



Translation: you may have plans to explore Naples.



You may also cancel them and stay by the pool.



IMPORTANT PET POLICY: All pets must be approved PRIOR TO BOOKING and subject to a pet fee. Please contact the owner before booking. Reservations made with unapproved pets will be cancelled. NO CATS ALLOWED.



★ WHY YOU'LL LOVE TROPICAL OAKS ESTATE



✔ 3.8-acre private estate

✔ Approx. 300 ft of canal frontage

✔ Fully renovated mid-century boho design

✔ 4 spacious bedrooms

✔ 40-foot saltwater pool + spa

✔ 2,000+ sq. ft. screened pool lanai

✔ Gourmet kitchen with 36 Italian range

✔ Wet bar with wine + beverage refrigerators

✔ Huge 10-foot dining table

✔ 90 Samsung QLED TV

✔ Multiple indoor gathering areas

✔ Beach cruiser bicycles

✔ Beach gear

✔ High-speed Wi-Fi

✔ Free private parking



This isn't just a place to sleep between beach days.



Tropical Oaks Estate is part of the vacation.



★ THE ESTATE



From the moment you walk inside, the home feels open, relaxed and just a little unexpected.



The fully renovated interior blends mid-century character with modern boho style — warm textures, natural materials, comfortable furnishings and plenty of Florida sunshine.



Large windows and doors connect the living spaces to the pool and tropical grounds, giving the entire home an easy indoor-outdoor feel.



There's room to gather.



There's room to spread out.



And on 3.8 acres, there is definitely room to breathe.



★ LIVING SPACES — PICK YOUR FAVORITE SPOT



Tropical Oaks Estate was designed for groups who actually want to spend time together.



Gather around the fireplace for cocktails and conversation, sink into the sectional for movie night, or open the doors and let the evening migrate outside toward the pool.



The main TV area includes an enormous 85 Samsung QLED Smart TV — because occasionally even paradise needs a movie night.



✔ Fireplace seating area

✔ Comfortable sofa + lounge chairs

✔ Large TV lounge

✔ 90 Samsung QLED TV

✔ Reading lights

✔ Direct pool access



The hardest decision may be whether to stay inside or head back out to the pool.



We recommend the pool.



★ THE KITCHEN — FOR PEOPLE WHO ACTUALLY LIKE TO COOK



The renovated gourmet kitchen is built for everything from coffee and pancakes to big family dinners.



At the center is generous quartz counter space and a large kitchen bar, while a 36 Italian range and oven makes cooking for a crowd considerably more enjoyable.



You'll also find:



✔ Built-in microwave

✔ 36 Italian stove + oven

✔ Refrigerator/freezer with ice + filtered water

✔ Second full refrigerator in the garage

✔ Dishwasher

✔ Keurig

✔ Drip coffee maker

✔ Nespresso

✔ French press

✔ Double KitchenAid toaster

✔ Electric kettle

✔ Cookware, dishes and glassware

✔ Pots, pans and cooking essentials



And because vacations sometimes require more than coffee...



★ THE BAR



Tropical Oaks Estate also has a dedicated wet bar with:



✔ Sink

✔ Beverage refrigerator

✔ Wine refrigerator



Cocktail hour has its own headquarters.



★ DINING — EVERYONE ACTUALLY FITS



No awkward folding chairs required.



The impressive 10-foot dining table seats 10, while the kitchen bar provides seating for another 6.



✔ Dining table for 10

✔ Kitchen bar seating for 6



It's equally suited to a big family dinner, takeout night or a long evening of wine, cards and questionable vacation stories.



★ 4 BEDROOMS



After the pool, beach, bikes and whatever else Naples throws at you, everyone has a comfortable place to retreat.



♛ PRIMARY BEDROOM



King bed

Private ensuite

Direct pool access

50 4K Smart TV



♛ BEDROOM 2



King bed

43 4K Smart TV



♛ BEDROOM 3



Queen bed

Private lanai

43 4K Smart TV



♛ BEDROOM 4



Queen bed

Twin XL bunk bed

43 4K Smart TV



Each bedroom includes comfortable linens, pillows, bedside tables, reading lights and its own Smart TV.



And yes — all bedding, including duvet covers, is washed between every stay.



Because luxury should also be very clean.



★ BATHROOMS



The home includes two full indoor bathrooms plus a powder room, as well as a convenient outdoor shower and toilet room for pool days.



The primary bathroom features:



✔ Soaking tub

✔ Shower

✔ Quartz vanity

✔ Fresh towels

✔ Essential toiletries



The additional bath spaces are similarly stocked so you can pack a little lighter.



The outdoor shower may become your favorite after a long day in the pool.



★ THE 40-FOOT POOL + SPA



This is the part you'll probably tell your friends about.



The enormous 40-foot saltwater pool and spa sits inside more than 2,000 sq. ft. of screened outdoor living space, surrounded by marble decking and views across the private estate and canal.



Swim laps before breakfast.



Float all afternoon.



Move to the spa after sunset.



Repeat as necessary.



✔ 40-foot saltwater swimming pool

✔ Spa

✔ 2,000+ sq. ft. screened lanai

✔ Marble pool deck

✔ Covered outdoor area

✔ Lounge space

✔ Patio lighting

✔ Automated saltwater pool system

✔ Estate + canal views

✔ Exceptional privacy



Unlike many Naples pool homes, you're not looking directly into somebody else's backyard.



Instead, you have acres of space, tropical landscaping and waterfront views.



That's the difference.



★ 3.8 ACRES OF YOUR OWN LITTLE NAPLES



Tropical Oaks Estate isn't called an estate because it sounded good in the listing.



The property sits on approximately 3.8 acres, creating a level of space and privacy that's difficult to find this close to central Naples.



With tropical landscaping and roughly 300 feet of canal frontage, the setting feels secluded without putting you far away from the places you actually came to see.



Morning coffee is quieter here.



Pool days feel more private.



And evenings have considerably fewer neighbors.



★ BEACH DAYS MADE EASY



When you eventually decide to leave the pool, Naples is waiting.



The home includes:



✔ Beach cruiser bicycles

✔ Beach accessories



Pack up, head toward the Gulf and make a day of it.



Then come home to your own pool and spa.



It's a pretty good system.



★ LOCATION



Tropical Oaks Estate gives you the best of both sides of Naples:



space and privacy at home, with downtown and the Gulf still close by.



The property is approximately 5 miles from the ocean and convenient to:



✔ Fifth Avenue South

✔ Third Street South

✔ Naples beaches

✔ Restaurants

✔ Shopping

✔ Golf and country clubs

✔ Local attractions



Spend the day exploring Naples.



Then leave the crowds behind and come home to the estate.



★ OPTIONAL EXTRAS & IMPORTANT DETAILS

Pool Heat



Pool heat may be added for:



June 1 – September 30: $30/night

October 1 – May 31: $45/night



Pets



Pets may be considered with prior owner approval.



Approved pets are subject to a $300 pet fee.



Please contact us before booking if you plan to bring a pet.



Visitors & Events



Tropical Oaks Estate is designed for relaxing vacations and gatherings among registered guests — events and parties are not permitted.



A maximum of 4 non-registered daytime visitors may be at the property at any one time.



Non-registered visitors may not stay overnight.



Come for Naples.



Stay for the 40-foot pool.



Then wonder why every vacation rental doesn't come with 3.8 acres of its own.



Welcome to Tropical Oaks Estate by DL Vacation Rentals.

Read More Expand
  • Feature Features
  • Map Map
  • School District Availability
  • Review Review

Feature Features

  • PETS

    Pet Friendly Service Animals Exempt From Fees
  • BEACH

    Near The Beach
  • DINING

    Dining Table
  • SAFETY

    Carbon Monoxide Detector Installed (host Has Indicated There Is A Carbon Monoxide Detector On The Property) Deadbolt Lock Fire Extinguisher First Aid Kit Outdoor Lighting Smoke Detector Installed (host Has Indicated There Is A Smoke Detector On The Property)
  • BEDROOM

    4 Bedrooms Bed Sheets Provided
  • GENERAL

    Unit Size: 3500 Sq Ft (325 Sq M)
  • KITCHEN

    Blender Coffee/tea Maker Cookware/dishes/utensils Dishwasher Freezer Microwave Oven Refrigerator Stovetop
  • LAUNDRY

    Laundry Facilities Washing Machine And Dryer
  • PARKING

    Car Recommended Onsite Parking Onsite Parking Options Include A Garage
  • INTERNET

    Free WiFi, With Speed Of 500+ Mbps (good For 6+ People Or 10+ Devices)
  • OUTDOORS

    Balcony Barbecue Grill Firepit Garden
  • POOL/SPA

    Heated Pool Hot Tub Outdoor Pool Private Pool
  • BATHROOMS

    3 Bathrooms Bidet Hair Dryer Outdoor Shower Shampoo Shower Soap Toilet Paper Towels Provided
  • LANGS SPOKEN

    English French
  • THINGS TO DO

    Bicycle On Site Casino Nearby Cycling Nearby Ecotours Nearby Fitness Center Fitness Facilities Nearby Golf Nearby Horse Riding Nearby Marina Nearby Mountain Biking Nearby Swimming Nearby Water Park Wildlife And Game Walks Nearby
  • ENTERTAINMENT

    Arcade/game Room Books Games Music Library Stereo Video Games Video Library Smart TV With Cable/satellite Service
  • LIVING SPACES

    Fireplace Living Room Wood Stove
  • CLIMATE CONTROL

    Air Conditioning Heating
  • FAMILY FRIENDLY

    Children's Books Children's Dinnerware Children's Games Children's Toys Highchair Playground Travel Crib
  • LOCATION HIGHLIGHTS

    In The City Center Near A Health Or Beauty Spa Near A Hospital Near Outlet Shopping Near The Sea On The Lake On The River On The Waterfront
  • SERVICES AND CONVENIENCES

    Iron/ironing Board Wet Bar
  • SUITABILITY/ACCESSIBILITY

    Smoke-free Property

CheckIn Check-in : 04:00 PM CheckOut Check-out : 11:00 AM
No Wheelchair No smoking No pets Children allowed
Occupancy Max occupancy : 10

Map Map

School District Availability

Review Review

  • Mark C.

    Submitted Jun 6, 2026

    Stayed Jun 1, 2026

    Stunning property which is perfectly located for beaches, shops etc in Naples. House is stocked with all appliances that you could possibly need. The house is probably the best maintained rental property I have stayed in with a fantastic pool.

  • Sandra M.

    Submitted Jun 1, 2026

    Stayed May 29, 2026

    This is an amazing property. They literally have everything you need. Communication was excellent. I would highly recommend this property.

  • Jacqueline L.

    Submitted May 17, 2026

    Stayed May 15, 2026

    Every room was very clean and appealingly put together.The pool area was excelently setup for entertaining.We were WOWED!

  • Jonathan D.

    Submitted May 14, 2026

    Stayed May 12, 2026

    The house was just as advertised! Clean and very well maintained. Pool was great. The property manager was very helpful, easily reachable and always available for assistance. Would highly recommend this property!!

  • Julie G.

    Submitted May 12, 2026

    Stayed May 8, 2026

    This was one of the most beautiful places I’ve ever stayed not a big traveler, but certainly have moved around a little bit. The host was an excellent communicator. The home is described exactly. We are planning our next trip as a group and will be booking again. The home is perfect for several couples.

  • Trisha M.

    Submitted May 9, 2026

    Stayed Apr 24, 2026

    I will say the pool was pretty deep right off the steps so we were on floats most of the time. But the house has everything you could want or need and it was very clean. We had a wonderful time!

  • Grant B.

    Submitted Apr 3, 2026

    Stayed Mar 27, 2026

    This house had EVERYTHING - highly recommend and we plan to rent again. The pool and outside amenities were first class and perfect for kids and adults. The house and all furnishings were very nice and high end. The extras - beach chairs, bikes, fishing poles, etc were a great touch

  • Cassandra B.

    Submitted Mar 18, 2026

    Stayed Mar 13, 2026

    Beautifully remodeled home that served as a base for our spring break adventures. Kids and adults alike loved the pool and lanai area. The kids caught a couple fish in the back yard and enjoyed the bikes. We were happy to see more than 10 beach chairs, a wagon, cooler and beach umbrellas. These extras allowed us to truly enjoy the beaches of Naples. I also appreciated a phone call from the owner when we arrived to make sure everything was okay.

  • Ellen M.

    Submitted Mar 10, 2026

    Stayed Feb 28, 2026

    This place was perfect for our family of 6 plus an 11 month old. All week we found new amenities that we were impressed with. Tons of attention to detail and all your needs taken into consideration. Communication before during and after our stay was exceptional and very helpful. We would definitely stay here again.

  • Karen W.

    Submitted Jan 25, 2026

    Stayed Jan 22, 2026

    We had a wonderful stay at Tropical Oaks. Derek was a fantastic host - proactive, responsive, welcoming, and easy to communicate with. The welcome snacks were a nice touch and made us feel right at home. The accommodations were clean, beds and furniture comfortable, and well cared for, and the property itself is beautiful.Everything you could want for pool and beach entertainment was available, and the kitchen was impressively well stocked with everything needed for meal prep and serving. We never felt like anything was missing. The home was super clean, communication throughout our stay was excellent, and the checkout procedures were straightforward and easy.Overall, a very enjoyable and stress-free stay. We would absolutely recommend Tropical Oaks and would be happy to return.

  • Leo L.

    Submitted Jan 20, 2026

    Stayed Jan 15, 2026

    This place is rated 10 out of 10 for a reason. Everything about the property is outstanding. The lot is private and huge. You will not see another person while you were there unless you want to. Everything from the bedrooms to the living areas to the garage and pool areas is well stocked with everything you could possibly need. The bedrooms are wonderful, beds are very comfortable. Kitchen and living areas are spacious and relaxing. The pool area is outstanding. Derek is a great communicator and made everything so easy.Do yourself a favor, just go ahead and rent this place. You will not regret it.

  • Carlie S.

    Submitted Dec 18, 2025

    Stayed Dec 11, 2025

    What a beautiful home! The perfect stay for our family while we visited Naples. The house had everything you could need and more. Perfect pool / lanai area, massive kitchen, comfortable beds. We will absolutely be back!

  • Michael B.

    Submitted Nov 29, 2025

    Stayed Nov 21, 2025

    Great stay and experience!

  • Cherna P.

    Submitted Oct 27, 2025

    Stayed Oct 22, 2025

    The home was beautiful and so enjoyable to stay at. Everything about our stay was exceptional. And the host was very accommodating and responsive to all of our needs. We will definitely be back and stay at the same place.

  • Rich H.

    Submitted Oct 24, 2025

    Stayed Oct 9, 2025

    Boho Beautiful. Very private location but close to all of Naples attractions. Great indoor outdoor living with awesome pool.

  • Lee A.

    Submitted Sep 26, 2025

    Stayed Sep 8, 2025

    We had a truly wonderful stay at this beautiful home, which exceeded all our expectations. The house was immaculately clean, spacious, and tastefully decorated throughout. The kitchen was exceptionally well-equipped — stocked with everything you could possibly need and more.The bedrooms were generously sized with very comfortable beds, and the entire property felt thoughtfully designed for relaxation and convenience. The outdoor space was equally impressive, featuring a vast pool, probably the largest we've ever experienced which was surrounded by ample lounge chairs, a large dining table, and a covered seating area with comfy egg chairs and even an outdoor TV.The host was easily reachable and responded promptly to any queries. We especially appreciated the unexpected welcome pack, and found the local guides and recommendations extremely helpful.The location was perfect for our needs, and we’re already planning to re-book for next year. We would highly recommend this property to anyone looking for a luxurious and stress-free stay.

  • Nancy G.

    Submitted Aug 12, 2025

    Stayed Aug 2, 2025

    It’s hard to get the family all together at the same time but we finally were and this house was perfect. It gave all three couples their own space as well as a room for the baby. The pool and outside area as well as the inside of the house are fully equipped and tastefully decorated. Just as pictured online

  • Lisa Y.

    Submitted Jul 6, 2025

    Stayed Jun 28, 2025

    We had an incredible stay! From the moment we arrived, we were blown away by how spacious and private the property felt. The huge pool easily fit all 6 of us and became our favorite hangout spot. The spacious outdoor seating made it easy to relax and socialize late into the evening. Inside, the home is large and never felt crowded. The kitchen was very well stocked for all our cooking and grilling needs. Even the decorative guitar on the wall tuned nicely- for my husband to play! The home sits on a large, private lot, which made it feel like a true retreat, yet it’s only a 15-minute drive to amazing downtown Naples restaurants and beaches. Couldn’t have asked for a better place. Highly recommend!

  • John G.

    Submitted Jun 28, 2025

    Stayed Jun 22, 2025

    Traveled to Naples with 10 family members to end the beach. House was just as described. Clean and with plenty of room and many extras.

  • Tyler M.

    Submitted May 28, 2025

    Stayed May 14, 2025

    Great stay, great service

  • Jessica P.

    Submitted Feb 7, 2025

    Stayed Jan 30, 2025

    Stayed at this property in February with my family of 7 adults and 1 child under two. The house was extremely well-equipped (everything you could ever possibly need), spotlessly clean, and exceedingly comfortable for our group. The pool area is huge and beautiful, and we spent most of our days hanging on the patio enjoying the weather. Derek, the owner, was incredibly proactive about checking in and responsive to any questions that we had. We will definitely be back to stay again!

  • aaron b.

    Submitted Jan 18, 2025

    Stayed Jan 12, 2025

    We spent 3 nights at this lovely home, and found it to be perfect for our needs. It was extremely clean, uncluttered, cutely decorated, and very comfortable. It was close to everything, and had a lovely large and private backyard. We were very happy with our choice, and would come back again. It would be a great retreat for a large family or group. as it was very spacious with lots of room for guests! Oh and we loved the pool area, and our host was very accomodating. Thank you Derek!

  • Nicholas B.

    Submitted Dec 22, 2024

    Stayed Nov 18, 2024

    Awesome property with everything you could

  • Henry F.

    Submitted Nov 13, 2024

    Stayed Nov 8, 2024

    Beautiful property in a Beautiful neighborhood.

  • Linda M.

    Submitted Oct 24, 2024

    Stayed Oct 18, 2024

    9 of us came to Naples to celebrate two of the girls birthday’s. Derek was excellent with communication and support …he even programmed the doorbell to ring “happy birthday “. It was so beautiful we decided to stay in on Saturday to lounge around the pool!

  • Lisa P.

    Submitted Sep 29, 2024

    Stayed Sep 21, 2024

    Everything very clean and comfortable. Decorated nicely.

Your dates are Available!

Total

Includes taxes and fees
$1,047+
View details