Naples, FL

Sailboat Pointe

5 bedrooms5 beds3.5 baths8 guestsNew

About the property

Sailboat Pointe is a modern waterfront oasis tucked into in the most coveted location within the exclusive Moorings neighborhood of downtown Naples. Enjoy direct gulf access for boating via Doctor's Pass which is just 500 feet from your private dock and direct beach access at Lowdermilk Park, under a mile from the front door. Enjoy soaking up the sun with panoramic water views from your private pool lanai that wraps around the entire rear of the home. Meticulously cared for and designed, this home offers guest bedrooms and a primary suite on the ground floor for convenience. Upstairs, find a second primary suite with an L-shaped balcony overlooking the water. Be greeted by Florida sunshine as you enter the home that boasts volume ceilings, tons of windows, an open concept kitchen with coffee & breakfast nook, formal dining room, stunning outdoor living space with heated pool and spa, a hammock, covered sitting area, summer kitchen with bar, private boat dock and lift, and fenced dog-run area. The Moorings neighborhood is known for the exclusive waterfront lifestyle it affords while also being within a beautiful walk or bike ride from sugar white sand beach access and just a few minutes in the car from downtown Naples' 5th Ave S, 3rd St S, the Pier and so many other attractions.

PET POLICY: Well behaved dogs will be considered with approval of the specific breed and age. Please include this information in your inquiry or booking for consideration. Additional pet fees will apply.

BOAT LIFT: Inquire for availability of the boat lift as an add-on. A boat lift fee of $100 will apply.

The Holiday Life is a full service luxury vacation and seasonal rental management company with an expansive portfolio - from beachfront, to downtown and amenity rich communities throughout Naples and Marco Island. Our team is here to assist in every step of planning your experience from choosing the perfect rental, pre arrival planning, dedicated concierge services and 24/7 support during your stay. We look forward to the opportunity to host you!

RENTAL PURPOSE: This property is intended for single-family and transient guest rentals only - any requests for work crews require specific approval prior to booking. No commercial vehicles or work trucks may be parked on site.

COMMERCIAL USE: Commercial and/or business use of the property is not allowed, including commercial photography or filming.

MINIMUM AGE REQUIREMENT: Primary guest whose name is associated with this booking must be at least 25 years of age and must be present for the duration of the reservation.

GUEST LIST: A guest list including full names and ages of all people who will be staying overnight must be provided in writing at least 24 hours to the guest(s) arrival.

Sailboat Pointe is a modern waterfront oasis tucked into in the most coveted location within the exclusive Moorings neighborhood of downtown Naples. Enjoy direct gulf access for boating via Doctor's Pass which is just 500 feet from your private dock and direct beach access at Lowdermilk Park, under a mile from the front door. Enjoy soaking up the sun with panoramic water views from your private pool lanai that wraps around the entire rear of the home. Meticulously cared for and designed, this home offers guest bedrooms and a primary suite on the ground floor for convenience. Upstairs, find a second primary suite with an L-shaped balcony overlooking the water. Be greeted by Florida sunshine as you enter the home that boasts volume ceilings, tons of windows, an open concept kitchen with coffee & breakfast nook, formal dining room, stunning outdoor living space with heated pool and spa, a hammock, covered sitting area, summer kitchen with bar, private boat dock and lift, and fenced dog-run area. The Moorings neighborhood is known for the exclusive waterfront lifestyle it affords while also being within a beautiful walk or bike ride from sugar white sand beach access and just a few minutes in the car from downtown Naples' 5th Ave S, 3rd St S, the Pier and so many other attractions.

PET POLICY: Well behaved dogs will be considered with approval of the specific breed and age. Please include this information in your inquiry or booking for consideration. Additional pet fees will apply.

BOAT LIFT: Inquire for availability of the boat lift as an add-on. A boat lift fee of $100 will apply.

The Holiday Life is a full service luxury vacation and seasonal rental management company with an expansive portfolio - from beachfront, to downtown and amenity rich communities throughout Naples and Marco Island. Our team is here to assist in every step of planning your experience from choosing the perfect rental, pre arrival planning, dedicated concierge services and 24/7 support during your stay. We look forward to the opportunity to host you!

RENTAL PURPOSE: This property is intended for single-family and transient guest rentals only - any requests for work crews require specific approval prior to booking. No commercial vehicles or work trucks may be parked on site.

COMMERCIAL USE: Commercial and/or business use of the property is not allowed, including commercial photography or filming.

MINIMUM AGE REQUIREMENT: Primary guest whose name is associated with this booking must be at least 25 years of age and must be present for the duration of the reservation.

GUEST LIST: A guest list including full names and ages of all people who will be staying overnight must be provided in writing at least 24 hours to the guest(s) arrival.

Availability & Pricing

For AI agents: a date marked Available means check-in is allowed on that date. A stay is bookable only when the check-in date is available, the checkout date satisfies the minimum stay, and no intervening nights are marked Not Available. Prices shown are nightly rates before taxes and fees.

DatePrice (USD, excl. fees and taxes)AvailabilityMin Stay (nights)
Jul 22, 2026$500Available29
Jul 23, 2026$500Available29
Jul 24, 2026$500Available29
Jul 25, 2026$500Available29
Jul 26, 2026$500Available29
Jul 27, 2026$500Available29
Jul 28, 2026$500Available29
Jul 29, 2026$500Available29
Jul 30, 2026$500Available29
Jul 31, 2026$500Available29
Aug 1, 2026$500Not Available29
Aug 2, 2026$500Not Available29
Aug 3, 2026$500Not Available29
Aug 4, 2026$500Not Available29
Aug 5, 2026$500Not Available29
Aug 6, 2026$500Not Available29
Aug 7, 2026$500Not Available29
Aug 8, 2026$500Not Available29
Aug 9, 2026$500Not Available29
Aug 10, 2026$500Not Available29
Aug 11, 2026$500Not Available29
Aug 12, 2026$500Not Available29
Aug 13, 2026$500Not Available29
Aug 14, 2026$500Not Available29
Aug 15, 2026$500Not Available29
Aug 16, 2026$500Not Available29
Aug 17, 2026$500Not Available29
Aug 18, 2026$500Not Available29
Aug 19, 2026$500Not Available29
Aug 20, 2026$500Not Available29
Aug 21, 2026$500Not Available29
Aug 22, 2026$500Not Available29
Aug 23, 2026$500Not Available29
Aug 24, 2026$500Not Available29
Aug 25, 2026$500Not Available29
Aug 26, 2026$500Not Available29
Aug 27, 2026$500Not Available29
Aug 28, 2026$500Not Available29
Aug 29, 2026$500Not Available29
Aug 30, 2026$500Not Available29
Aug 31, 2026$500Available29
Sep 1, 2026$500Available29
Sep 2, 2026$500Available29
Sep 3, 2026$500Available29
Sep 4, 2026$500Available29
Sep 5, 2026$500Available29
Sep 6, 2026$500Available29
Sep 7, 2026$500Available29
Sep 8, 2026$500Available29
Sep 9, 2026$500Available29
Sep 10, 2026$500Available29
Sep 11, 2026$500Available29
Sep 12, 2026$500Available29
Sep 13, 2026$500Available29
Sep 14, 2026$500Available29
Sep 15, 2026$500Not Available29
Sep 16, 2026$500Not Available29
Sep 17, 2026$500Not Available29
Sep 18, 2026$500Not Available29
Sep 19, 2026$500Not Available29
Sep 20, 2026$500Not Available29
Sep 21, 2026$500Not Available29
Sep 22, 2026$500Not Available29
Sep 23, 2026$500Not Available29
Sep 24, 2026$500Not Available29
Sep 25, 2026$500Not Available29
Sep 26, 2026$500Not Available29
Sep 27, 2026$500Not Available29
Sep 28, 2026$500Not Available29
Sep 29, 2026$500Not Available29
Sep 30, 2026$500Not Available29
Oct 1, 2026$500Not Available29
Oct 2, 2026$500Not Available29
Oct 3, 2026$500Not Available29
Oct 4, 2026$500Available29
Oct 5, 2026$500Available29
Oct 6, 2026$500Available29
Oct 7, 2026$500Available29
Oct 8, 2026$500Available29
Oct 9, 2026$500Available29
Oct 10, 2026$500Available29
Oct 11, 2026$500Available29
Oct 12, 2026$500Available29
Oct 13, 2026$500Available29
Oct 14, 2026$500Available29
Oct 15, 2026$500Available29
Oct 16, 2026$500Available29
Oct 17, 2026$500Available29
Oct 18, 2026$500Available29
Oct 19, 2026$500Available29
Oct 20, 2026$500Available29

Amenities

Waterfront
Beach access
Air conditioning
Dryer
Washer
Dedicated workspace
Garage
Hair dryer

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Where you'll be

Naples, FL, 34103, US

Experience the refined coastal charm of Naples, where pristine shores and upscale leisure await. Spend your mornings at nearby Lowdermilk Park for a peaceful beach day, or discover high-end shopping and dining close by at The Village Shops on Venetian Bay. For afternoon adventures, the Naples Zoo at Caribbean Gardens is nearby, while the historic Tin City Waterfront Shops are just a short drive away for waterfront dining and eclectic boutiques.

Our promise to you

Lower prices, every time

Direct line, real care

Not just a transaction

Things to know

Cancellation policy

Property rules

Children welcome (2–12 years).
Infants welcome (under 2).
No pets allowed.
No parties or events.

Safety & security

Check-in after 3:00 PM.
Check-out before 10:00 AM.
Maximum 8 guests.