The Club at Olde Cypress Naples

Discover vacation villas located approximately 20 minutes away from The Club at Olde Cypress in Naples. Perfect for golf enthusiasts seeking luxury, pool comfort, and proximity to one of Naples’ premier courses. Combine Florida’s coastal lifestyle with golf excellence in one trip.

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Vacation Rentals

6 available rentals

Attractive vacation home in the gated “Crown Point” community in Naples The house is surrounded by a tropical garden Entrance area of Villa Altaira
Florida Naples Vacation Home

Villa Altaira
From $ 2,050 / week

Two-story villa with south-facing terrace, spa, lake view & space for 8 – stylish vacation home in Naples.

  • Bedrooms Bedroom: 4 (King, 2 Queen, 2 Twin)
  • Bathrooms Bathroom: 3 1/2
Details
Beautiful pool with view of thel lake Covered pool terrace with dining table, sun loungers and private pool overlooking a tranquil lake and palm trees in Naples Beautiful pool with view of thel lake
Pet friendly
Florida Naples Vacation Home

Villa Astoria
From $ 1,650 / week

Two-story villa with lake view, pool, BBQ & prime Naples location – ideal for families and explorers in Crown Point community.

  • Bedrooms Bedroom: 4 (2 King, Queen, 2 Twins)
  • Bathrooms Bathroom: 3 1/2
Details
Exterior view of Villa Caressa Here you can swim your refreshing laps View from the pool to the greenery and the small lake
Pet friendly
Florida Naples Vacation Home

Villa Caressa
From $ 2,000 / week

South-facing terrace with pool & lake view, modern kitchen & Crown Point location – elegant villa for relaxing Naples days.

  • Bedrooms Bedroom: 3 (2 King, 2 Twin)
  • Bathrooms Bathroom: 2
Details
Spacious lakefront vacation home with four bedrooms The terrace and pool are surrounded by a white screen The electrically heated pool offers swimming fun in any weather
Pet friendly
Florida Naples Vacation Home

Villa Catalina
From $ 1,650 / week

Lakeview villa with 4 bedrooms & pool – ideal for families, BBQ evenings & relaxing days in sunny Naples.

  • Bedrooms Bedroom: 4 (King, 2 Queen, 2 Twin)
  • Bathrooms Bathroom: 2
Details
outside view from the Villa Crown Point the poolarea is perfect for relaxing Crystal clear water into the pool
Pet friendly
Florida Naples Vacation Home

Villa Crown Point
From $ 1,400 / week

Two-story villa with lake view, east-facing terrace & pool – elegant Naples retreat with space, comfort & privacy.

  • Bedrooms Bedroom: 4 (2 King, Queen, 2 Twin)
  • Bathrooms Bathroom: 3 1/2
Details
Beautiful lake front property in the Kings Lake community in Naples rocking chair for to enjoy the morning sun You can already enjoy the view of the pool, the terrace and the lake behind it while having breakfast
Pet friendly
Florida Naples Vacation Home

Villa Duchess
From $ 1,650 / week

Southwest terrace, large pool & lake view – charming Queens Park villa with summer kitchen, close to beach & town.

  • Bedrooms Bedroom: 3 (2 King, 2 Twin )
  • Bathrooms Bathroom: 2
Details

Championship Golf by P.B. Dye

The 18-hole course at Olde Cypress was designed by P.B. Dye, featuring a layout with water hazards, creative bunkering, and strategic challenges suited for players of many skill levels.

Facilities & Amenities

The club includes a distinguished clubhouse, practice facilities, tennis and pickleball courts, fitness center, and various sporting and social amenities for members and guests.

Vacation Homes Near Olde Cypress

Within the surrounding community, villas with private pools, spacious interiors, and tranquil settings are available—ideal for combining golf rounds with relaxation and comfort.

Explore Naples & Surrounding Attractions

Apart from golf, guests can enjoy Naples’ pristine beaches, excellent dining and shopping, and nature excursions by boat or kayak—everything within easy reach of your villa.

Course Information – The Club at Olde Cypress

The Club at Olde Cypress is a private, 18-hole championship course designed by P.B. Dye. It sits within a gated community spanning approximately 540 acres, combining top-tier golf design with elegant enclave living.

The club offers membership tiers (including non-resident options), practice and training facilities, tennis, pickleball, a fitness center, and a refined clubhouse with dining services. Its premium amenities and membership flexibility make it one of Naples’ standout golf communities.

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