The Riley
1 - 3 Beds
$1,712 - $3,133
$11,000 /month
2721 Olde Cypress Dr, Naples, FL 34119
Last Updated:
What This House Offers
Welcome to your private slice of Naples paradise at 2721 Olde Cypress Drive a home that feels less like a house and more like a private retreat sculpted around... the quintessential Florida lifestyle. This isn't just a living space,it's a story in architecture and atmosphere. Nestled in the gated Olde Cypress community,the address sits like a quiet crown jewel along a shimmering waterway and mature oaks,with the championship golf course threading gracefully through the neighborhood." where everyday living feels like a resort escape. Step inside and the home feels immediately intentional -every corner designed for comfort and connection. Natural light pours in through expansive windows,casting warm reflections across hand-finished floors and high ceilings that elevate the everyday. Available for Seasonal rent $14,500 per month and Annual per month $11,000
Unit
- $11,000 / month
- 4 Beds
- 4 Baths
- 3543 sq. ft.
- Available May 5
Home Features
- Dishwasher
- Freezer
- High Speed Internet Access
- Ice Maker
- Kitchen
- Microwave
- Range
- Refrigerator
- Wet Bar
Community Features
- Clubhouse
- Fitness Center
- Grill
- Pool
- Putting Greens
- Spa
- Tennis Court
2721 Olde Cypress Dr is a single-family home for rent in Naples, FL
Fees and Policies
The fees below are based on community-supplied data and may exclude additional fees and utilities.
One-Time Basics
Due at Move-In
- Security Deposit - Refundable$11,000
Property Fee Disclaimer Based on community-supplied data and independent market research. Subject to change without notice. May exclude fees for mandatory or optional services and usage-based utilities.
Home Details
Views
- Lake
- Golf Course
- Woods
Home Design
- Built in 2002
- Single Family Detached Home
Interior Spaces
- Furnished
- Tray Ceiling
- Wet Bar
- Ceiling Fan
- 3543 Sq Ft Home
- 1-Story Property
Kitchen
- Indoor Grill
- Gas Cooktop
- Freezer
- Ice Maker
- Microwave
- Dishwasher
Flooring
- Wood
- Tile
Bedrooms and Bathrooms
- Split Bedroom Floorplan
- 4 Full Bathrooms
- 4 Bedrooms | 4 Bathrooms
- 4 Bedrooms
Laundry
- Dryer
- Laundry Tub
- Washer
Home Security
- Fire and Smoke Detector
Parking
- 3 Car Attached Garage
- Garage Door Opener
Pool
- In Ground Pool
- In Ground Spa
Outdoor Features
- Outdoor Kitchen
- Outdoor Grill
Lot Details
- Lake Front
- 13504 Sq Ft Lot
Schools
- Laurel Oak Elementary School
- Dakridge Middle School
- Gulf Coast High School
Utilities
- Central Heating and Cooling System
- High Speed Internet
- Heating System Uses Gas
- Heating System Uses Propane
- Cable TV Available
- Underground Utilities
- Public Water Source
- Public Sewer
Listing and Financial Details
- Security Deposit $11,000
- Long Term Lease
- Legal Lot and Block 1 / 10
- Assessor Parcel Number 64625001420
- Tenant pays for application fee, electricity, internet, water
- The owner pays for cable TV, grounds care, pool maintenance
Community Details
Overview
- Private Membership Available
- Olde Cypress Subdivision
Amenities
- Clubhouse
- Restaurant
- Community Library
Recreation
- Golf Course Community
- Fitness Center
- Community Pool
- Community Spa
- Tennis Courts
- Putting Green
- Pickleball Courts
Pet Policy
- Pets allowed on a case-by-case basis
Security
- Gated Community
Explore Commute Options
Destination Address
- Drive Time--
- Walk Time--
- Bike Ride Time--
- Public Transit--
Get In Touch
Property Address: 2721 Olde Cypress Dr,
Naples, FL 34119
Naples, FL 34119
Listed by
Ivana Mladenovska | Realty One Group MVPPhone Number: (239) 530-8436
Information is provided by The Florida Gulf Coast Multiple Listing Service, Inc. Information deemed reliable but not guaranteed. All properties are subject to prior sale, change or withdrawal. Listing(s) information is provided exclusively for consumers' personal, non-commercial use and may not be used for any purpose other than to identify prospective properties consumers may be interested in purchasing. Copyright © 2026 The Florida Gulf Coast Multiple Listing Service, Inc. All rights reserved.
Area Scores
Walkability
Somewhat walkable20 / 100
Driveability
Exceptionally drivable90 / 100
Bikeability
Fairly bikeable40 / 100
Scores provided by 
Travel and Transit
Airport
Southwest Florida International
37 min Drive
Local Education
Primary and Secondary Schools
Laurel Oak Elementary School
Grades PK-5
Public
Oakridge Middle School
Grades 6-8
Public
Waves Of Wonder Montessori School
Grades PK-8
Private
Gulf Coast High School
Grades 9-12
Public
Adonai Academy Incorporated
Grades PK-12
Private
Data provided by GreatSchools.org © 2026. All rights reserved.
Colleges and Universities
School
Commute Time (Distance)
Hodges University, Naples
Drive: 6 min (2.3 mi)
SW Fla. Coll., Bonita Springs
Drive: 23 min (14.2 mi)
Discover Olde Cypress, Naples, FL
Shopping Centers
Shoppers will appreciate 2721 Olde Cypress Dr proximity to Logan Landings, Insignia Center, and Bougainvillea Center. Logan Landings is 1.2 miles away, and Insignia Center is within a 29 minute walk.
Airports
Living in Olde Cypress provides easy access to Southwest Florida International, located just 34 minutes from 2721 Olde Cypress Dr.
Protect yourself from fraud. Do not send money to anyone you don't know.
Nearby Properties You Might Like
Within 50 Miles of 2721 Olde Cypress Dr
Find More Rentals in Naples
- Houses with Pets Allowed in Naples
- Affordable Houses for Rent in Naples
- Fully Furnished Homes for Rent in Naples
- Modern Homes for Rent in Naples
- Houses for Rent with Pool in Naples
- Houses for Rent with a Yard in Naples
- Homes for Rent with a Garage in Naples
- Houses for Rent with Fireplace in Naples
- Houses for Rent with a Patio in Naples
- Houses for Rent with Washer and Dryer in Naples
- Houses for Rent with Utilities Paid in Naples