111 Caribbean Rd, Naples, FL 34108
Property image
Property image
FOR RENT

111 Caribbean Rd
Naples, FL 34108

Pine Ridge
  • 5 Beds
  • 6.5 Baths
  • 5,400 sqft
Price may not include required fees and charges.
Cost and fees breakdown

$50,000/mo

Original price: $60,000

$50,000/mo

Original price: $60,000
Price may not include required fees and charges.
Cost and fees breakdown
  • 5 Beds
  • 6.5 Baths
  • 5,400 sqft

Local Information

  • Map ViewExplore the area around 111 Caribbean Rd.
  • Schools1 Preschool School1 Elementary School1 Middle School1 High School
  • Shop & Eat
-- mins to
Commute Destination

Description

Available January 3rd to January 31st, 2027. Welcome to CocoBaba! This private 5BR, 6.5BA estate offers the ultimate Naples getaway with a detached guest house, sparkling pool & spa, and a PRIVATE lighted pickleball court for day or night play. Guests will love the dedicated kids' room, playroom stocked with toys, and extra child-size beds, while everyone can enjoy indoor/outdoor dining, a koi pond, and lush preserve-like grounds all just minutes from the beach and vibrant 5th Ave South. Inside, you'll find 5 bedrooms and 6.5 bathrooms, offering plenty of space for everyone to spread out. A private family/kids' room and a playroom stocked with toys (plus extra child-size air mattresses) make this home especially family-friendly. For those who need to stay connected, a dedicated workspace provides quiet focus. The home also features a fully livable detached guest house, perfect for added privacy. Step outside and enjoy resort-style amenities: Private pickleball and tennis court with lighting for daytime or nighttime matches Regulation Half Basketball Court Relaxing Court Side Lighted Tiki Hut with table for 4 and 2 hanging chairs Sparkling pool and relaxing spa for unwinding under the Florida sun Indoor and outdoor dining areas, ideal for large family meals Large balcony and viewing deck with serene views Koi pond tucked into the lush landscaping for a peaceful touch The location couldn't be better you're just a 4-minute drive to Clam Pass and Seagate beaches and about 12 minutes to the restaurants, galleries, and shops of 5th Avenue South in Olde Naples. Whether you're planning a family vacation, group gathering, or simply a private escape, Cocobaba delivers the perfect mix of relaxation, recreation, and luxury. Layout & Bedroom Breakdown: 1st Floor: Master Bedroom and ensuite bathroom - King sized bed Guest Bedroom and ensuite bathroom - King sized bed Sitting Room connected to Master Bedroom Powder Room Office Laundry Room Mud Room 2nd Floor: Guest Bedroom and ensuite bathroom - King sized bed Guest Bedroom and ensuite bathroom - King sized Bed Family Room with 2 child sized air mattresses Full Bathroom Guest House: Studio style - King sized bed, living room, full bathroom Availability: January 2nd to January 31st, 2027. Please note the following: Guests do not have access to garage. 10 Adult Guest Maximum No parties or events There is a front door camera, no cameras inside the property, exterior cameras are shut off for guest stays. Pool heat is limited to 85 degree cap, spa to 104 degrees. Tennis, Pickleball, and Basketball are limited to play hours of 8am to 9pm.

Costs and Fees

Required monthly rent & fees
  • Base rent
    $50,000/mo
Required one-time fees
  • Security deposit
    Contact for details
  • Application fee
    Contact for details
  • Administrative fee
    Contact for details
Pricing is subject to change. All calculations are estimates and provided for informational purposes only. Actual amounts may include additional mandatory or optional fees. Please consult the community manager for a complete breakdown of all rental costs.
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Home Highlights

Pets
No
Parking
Contact Manager
Outdoor
Pool
View
Contact Manager
Utilities
Contact Manager
Listed
49 days ago

Details for 111 Caribbean Rd

Interior Features

Heating & Cooling
Heating: Central, ElectricHeating Fuel: Central
Appliances & Utilities
DishwasherDisposalDryerMicrowaveWasher
Fireplace & Spa
Hot Tub or Spa
Levels, Entrance, & Accessibility
Floors: Tile, Wood

Days on Market

Days on Market: 49 days on Trulia

Property Information

Year Built
Year Built: 1999
Property Type / Style
Property Type: Single Family Home

Rental Terms, Policies & Fees

Lease Term: Contact For Details

Exterior Features

Pool
Pool

Agent Information

Listing Agent
MLS/Source ID: 226020180

Additional Information

Tennis Court(s)

Price History for 111 Caribbean Rd

DatePriceEventSource
06/26/2026$50,000PriceChange
NABOR FL #226020180
05/26/2026$60,000Listed For RentNABOR FL #226020180
10/16/2025$1,320,550Sold
N/A
03/01/2021$2,175,000Sold
N/A
01/30/2021$2,399,000PendingN/A
01/23/2021$2,399,000PriceChange
N/A
01/16/2021$2,275,000Listed For SaleN/A
10/17/2012$785,000Sold
N/A
09/14/2012$689,900Listed For SaleAgent Provided
07/17/2010$2,295,000ListingRemovedAgent Provided
06/15/2010$2,295,000PriceChange
Agent Provided
12/16/2009$2,290,000Listed For SaleN/A
09/02/2009$2,295,000ListingRemovedAgent Provided
05/24/2009$2,295,000PriceChange
Agent Provided
11/22/2008$2,390,000PriceChange
Agent Provided
04/23/2008$2,690,000Listed For SaleAgent Provided
11/05/1998$299,000Sold
N/A
06/05/1997$260,000Sold
N/A

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Affordability

TIP:Try to keep your rent within a third of your gross household income. Learn why in our Renter's Guide.
For this property
$1,800,000 PER YEAR
is the suggested income
Win over prospective landlords with your smart budgeting. As a good rule of thumb, ideally you would have at least three times your monthly rent in combined household income.

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Assigned Schools

These are the assigned schools for 111 Caribbean Rd.
View nearby schools on GreatSchools
The GreatSchools Rating compares schools on a variety of school quality indicators including test scores, college readiness, equity and more. Learn more.

Neighborhood Overview

Pine Ridge
See Local Highlights
Neighborhood stats provided by third party data sources.

What Locals Say about Pine Ridge

At least 21 Trulia users voted on each feature.

  • 90 % Say it's quiet

  • 89 % Say parking is easy

  • 88 % Say it's dog friendly

  • 74 % Say it's walkable to restaurants

  • 74 % Say car is needed

  • 68 % Say people would walk alone at night

  • 67 % Say they plan to stay for at least 5 years

  • 64 % Say streets are well-lit

  • 64 % Say there are sidewalks

  • 63 % Say there's holiday spirit

  • 58 % Say it's walkable to grocery stores

  • 52 % Say yards are well-kept

  • 40 % Say neighbors are friendly

  • 34 % Say there's wildlife

  • 27 % Say there are community events

  • 19 % Say kids play outside

Sourced by Trulia users. Learn more about our methodology.
  • Enright
    "Convenient to Mercado for shopping and eating. Can walk to 2 grocery stores and 2 movie theaters. Several restaurants, banks and dry cleaners you are able to walk to."
    1
    Flag
  • BJE
    "Only 1.5 miles to beach, public transportation available, a variety of restaurants in walking distance, walk to 2 grocery stores and shopping & dining at the Mercado."
    10
    Flag
  • kochava72
    "close to an awesome bike shop!"
    0
    Flag

Local Legal Protections

LGBTQ • Source of Income

Nearby homes for rent

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111 Caribbean Rd, Naples, FL is a 5 bedroom, 7 bathroom, 5,400 sqft single-family home built in 1999. 111 Caribbean Rd is located in Pine Ridge, Naples. 111 Caribbean Rd was listed for rent for $50,000/month on May 26, 2026.