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Popular penthouses
Naples Escape - The Oasis
Naples, FL50 guests
Naples Escape - The Oasis. Welcome to Naples Escape The Oasis, a private estate in Naples, Florida designed for peaceful, creative and refined gatherings. This modern contemporary retreat is best suited for photography, film production, content creation, quiet gatherings and small low impact events.
The property is intentionally maintained
...
From
$500
/hr
4 hr min
Remote Workspace and Reading Lounge
Serving the Naples, FL area10 guests
Remote Workspace and Reading Lounge. Cozy suite designed for laid back gatherings like movie nights, book clubs, game nights, brainstorming sessions, or casual meetups with friends and colleagues. The space is filled with comfortable couches that create a relaxed, inviting atmosphere perfect for unwinding and connecting. Includes a smart TV with
...
From
$75
/hr
1 hr min
The Florida Betty
Serving the Naples, FL area5.0 (2)
50 guests
The Florida Betty. The Florida Betty is a throwback to nostalgic florida. With original terazzo floors, a turquoise fridge an out door bar and entertaining area and tons of pink it is the perfect location for hosting your event. We have had photo shoots, yoga retreats ,bachelorette
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From
$75
/hr
4 hr min
Lorraine 55 Estate
Serving the Naples, FL area15 guests
Lorraine 55 Estate. 📋 House Rules
To ensure a smooth experience for all guests and to maintain the quality of the space, the following rules must be followed at all times:
General Use
Daytime events only
All bookings must conclude by 1:00 PM to allow for proper reset and preparation
Access is limited to
...
From
$135
/hr
4 hr min
The Parsonage
Serving the Naples, FL area5.0 (4)
25 guests
The Parsonage. 1925 Spanish style home. We are located in the River District. Our home has parking for 15 vehicles. There is a large porch in the front and a fenced in private pool area.
The interior has several brick walls, a large kitchen, a downstairs bathroom and a
...
From
$65
/hr
3 hr min
Single-Family Home for your next Event
Park Shore, Naples, FL12 guests
Step into our vibrant and welcoming haven, ideal for brand photography, family photos, mini sessions, lifestyle shoots, and so much more! Our home features a stunning outdoor lanai, perfect for capturing natural light and organic moments. Dive into creativity with our picturesque pool as your backdrop.
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From
$140
/hr
4 hr min
Beautiful and Spacious Gated Home with a Guest House
Rural Estates, Naples, FL25 guests
Located in NE Naples. Beautiful gated 4bd/2.5ba, a full office with monitor, printer and wifi. A full 1/bd 1/ba guest home on the 1.5 acres. Kitchens are fully equipped with all the amenities including a washer and dryer in both houses. The main house includes a
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From
$225
/hr
4 hr min
Spacious Urban Estate Home with Open Layout and Lake View
Serving the Naples, FL area70 guests
Nestled in the beautiful city of Ave Maria estate home with tall 12 ft ceilings equipped with home office with high speed wifi and wired internet, 3 bed/3 bath huge open layout with large master bed, kitchen, family room. The great room is the focal point
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From
$370
/hr
4 hr min
Beautiful Ranch Space
Serving the Naples, FL area5.0 (1)
15 guests
Our Space is a beautiful space that is meant for celebrations and gatherings. HOP Ranch features a pool, hot tub, bonfire pit, covered picnic area with power, arena, viewing deck, dock on a large pond, permaculture food forest garden, multiple patios and seating areas, an ATV
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From
$600
/hr
2 hr min
Spacious Home Perfect for Retreats/Events
Serving the Naples, FL area5.0 (4)
40 guests
Our space is just as it sounds. An oasis retreat with everything that SWFL has to offer. GREAT for small get togethers like birthdays, showers, bachelor/bachelorette parties, etc. The open floor plan will allow a group of 20 or more. Hang out by the pool, or
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From
$300
/hr
4 hr min
Modern house with Resort Venue by the Mackinac Canal
Serving the Naples, FL area50 guests
Welcome to your dream getaway in Cape Coral, Florida! Our luxurious canal front retreat offers 4 bedrooms and 3 bathrooms, perfect for vacations, weddings, bridal party preparations, and reunions for up to 50 guests but a maximum of 13 overnight guests. Enjoy a fireplaced living room,
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From
$750
/hr
4 hr min
Private Canal Front Heated Pool Retreat
Serving the Naples, FL area25 guests
Welcome to our centrally located haven in Cape Coral, Florida, where our spacious and versatile home awaits you. Situated just minutes away from an array of exciting attractions, our property provides the perfect hub for gatherings, events, and various celebrations. Let's dive into the description, highlighting
...
From
$197
/hr
3 hr min
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Updated July 29, 2026Our data is refreshed in real time using booking trends, verified guest reviews, and direct partner updates — with additional quality checks from our team.