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Sterling Oaks (Naples, Florida) Vacation Rentals

(8 rentals)
Naples House
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Vanderbilt Beach Award Winning and Barefoot Beach

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Very Private - Absolutely beautiful. Full of wildlife. Two of the last four years, our guest have purchased in our Sterling Oaks community after renting our place. Everyone loves it here.AVAILABLE: 2026 - January 1 to April 1 for a three month lease: Our Sterling Oaks Home $7,470 month. Or you could...

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$117
avg per night
Naples Townhome
Sleeps 4, 2 bedrooms, 2 bathrooms

Distance to beach: 4 miles to Bonita Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Beautiful Coach home in the Gated neighborhood of Sterling Oaks. Sterling oaks offers resort style pool with a tiki bar that has wonderful food and drinks. The club house offers dinner every Friday night and pub night on Tuesdays nights. You can also join the many events and leagues we offer during...

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Naples House
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 5 miles to Delnor-Wiggins Pass

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Discover Resort-Style Living in Sterling Oaks – North Naples’ Premier Pickleball & Tennis CommunityWelcome to Wildcat Cove in Sterling Oaks, one of North Naples’ most desirable gated communities, where this charming two-story home offers the perfect blend of privacy, comfort,...

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$168
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms
1 review

Distance to beach: 3 miles to Bonita Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

This condo is located in North Naples in the much sought out gated community of Sterling Oaks. CLOSE TO BEACHES. Unit consists of 3 bedrooms and 2 full baths, living room, dining area, large kitchen plus breakfast bar and an enclosed lanai. There’s covered parking at your door and additional parking...

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Featured review

"Two month stsy"

Susan was a great host. She met us at the condo and had little welcoming touches thoughout. The condo split layout worked great when our kids and grandkids visited. We enjoyed the community and amenities....

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$155
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

Gorgeous 3 bed/2bath furnished condo only three miles form one of the finest beaches in Florida. This second floor end unit comes with lots of bright sunlight and everything has been updated. Enjoy a fantastic full view overlooking the all natural Florida preserve and clubhouse which is spectacular after...

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Naples Apartment
Sleeps 4, 2 bedrooms, 1.5 bathrooms

Key Amenities

  • Air conditioning
  • Pool
  • Rentals by owner
  • WiFi

About this property

This lovely condo has everything you need for a wonderful stay in Naples. Open plan large living area, with views over a natural preserve lake. The accommodation comprises spacious air-conditioned rooms with vaulted ceilings all decorated Florida style. Sterling Oaks has a fantastic Club House and...

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$143
avg per night
Naples Condo
Sleeps 6, 3 bedrooms, 2 bathrooms

Distance to beach: 5 miles to Bonita Beach, Barefoot Beach

Key Amenities

  • Air conditioning
  • Hot tub
  • Pool
  • Rentals by owner
  • WiFi

About this property

Large Carriage House Condo FOR RENT @ , Florida. Available from April 2024.....minimum 30 day/monthly rental 3 bedroom + den + 2 baths, 1829 Sqft 2nd floor, lake view April 2024 - #4500+ Taxes & Fees May 2024 -Sept 2024: $3500/mo + Taxes & Fees October 2024 - Dec 2024: 4500/mo + Taxes &...

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$97
avg per night
Naples House
Sleeps 6, 3 bedrooms, 3 bathrooms

Distance to beach: 5 miles to Delnor-Wiggins Pass State Park

Key Amenities

  • Air conditioning
  • Private pool
  • Rentals by owner
  • WiFi

About this property

AVAILABLE FOR SEASONAL AND LONG-TERM RENT:Jan-Mar 2026 N/A April 2026 $6,000 May-Oct 2026 $4,000 Nov 2026 $5,000 Dec 2026 $6,000 Jan-Mar 2027 $10,000 ask about other months annual $4,500/mo11% Florida Tourist Tax is extra for rentals less than 6 months. 2 months term or longer is preferred....

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$267
avg per night
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