Listing Provided Courtesy of ALL IN PROPERTY MANAGEMENT LLC
LUXURY WINDING CYPRESS VACATION RENTAL IN NAPLES FLORIDA / BACKYARD OASIS WITH A PRACTICE PUTTING GREEN, INFINITY SPA, FIRE TABLE AND OVERSIZED HEATED POOL. NOW BOOKING SEASON 2027
7052 Live Oak Drive is Your Private Southwest Florida Escape. The ideal home for vacation getaways or extended stays all year round. This 2 Bed, 2 Bath Home with a Den / Office offers 2 King Beds and all the comforts of then … and then some! It is ideally located in a quiet, highly sought-after neighborhood just minutes from the area’s best beaches, public golf courses, dining, and shopping. This beautiful single family home offers the ideal blend of comfort, luxury, privacy, and convenience for your family’s next vacation. The Winding Cypress community is just a short drive to world-famous Gulf beaches, championship golf courses, and popular destinations like Fifth Avenue South and Mercato.
Step inside to a bright, open layout designed for relaxing and entertaining. The spacious living areas flow seamlessly into a well-appointed kitchen, creating the perfect space to gather with family and friends. Enjoy the true Florida lifestyle outdoors with an extra-large private lanai – perfect for morning coffee, evening cocktails, or simply soaking in the warm sunshine. Whether you’re here to relax, explore, or enjoy the sunshine, this home offers everything you need for an unforgettable stay.
Adjacent to the Picayune Strand Forest, with Tile Floors throughout / No Carpet in this home. Situated on a Lakefront Lot with Outdoor Putting in backyard, an Outdoor Gas Grill, Fire Table, Dining area and the most amazing pool and spa. There are Beach Chairs, 4 Bicycles and a variety of workout equipment provided in the garage. The Extended Driveway offers plenty of room for parking.
The Winding Cypress Community offers the most impressive amenities, including a resort style pool with a waterfall, a spa, an on-site restaurant – The Shady Palm Cafe, a fitness center, movement room, miles of nature trails, a clubhouse and over 800 acres of natural preserves polished of by a wooden boardwalk.
*This is a Pet Free Vacation Rental. The owners have installed a UV Light in the A/C System
*All applicants will have to fill out the HOA application online through Tenant Evaluation
*Applications must be submitted at least twenty (20) days prior to occupancy / Start of the lease
*Application Fees (Paid by tenant directly) is $250.00 Per Individual age 18 + Over
7052 Live Oak Drive is Your Private Southwest Florida Escape. The ideal home for vacation getaways or extended stays all year round. This 2 Bed, 2 Bath Home with a Den / Office offers 2 King Beds and all the comforts of then … and then some! It is ideally located in a quiet, highly sought-after neighborhood just minutes from the area’s best beaches, public golf courses, dining, and shopping. This beautiful single family home offers the ideal blend of comfort, luxury, privacy, and convenience for your family’s next vacation. The Winding Cypress community is just a short drive to world-famous Gulf beaches, championship golf courses, and popular destinations like Fifth Avenue South and Mercato.
Step inside to a bright, open layout designed for relaxing and entertaining. The spacious living areas flow seamlessly into a well-appointed kitchen, creating the perfect space to gather with family and friends. Enjoy the true Florida lifestyle outdoors with an extra-large private lanai – perfect for morning coffee, evening cocktails, or simply soaking in the warm sunshine. Whether you’re here to relax, explore, or enjoy the sunshine, this home offers everything you need for an unforgettable stay.
Adjacent to the Picayune Strand Forest, with Tile Floors throughout / No Carpet in this home. Situated on a Lakefront Lot with Outdoor Putting in backyard, an Outdoor Gas Grill, Fire Table, Dining area and the most amazing pool and spa. There are Beach Chairs, 4 Bicycles and a variety of workout equipment provided in the garage. The Extended Driveway offers plenty of room for parking.
The Winding Cypress Community offers the most impressive amenities, including a resort style pool with a waterfall, a spa, an on-site restaurant – The Shady Palm Cafe, a fitness center, movement room, miles of nature trails, a clubhouse and over 800 acres of natural preserves polished of by a wooden boardwalk.
*This is a Pet Free Vacation Rental. The owners have installed a UV Light in the A/C System
*All applicants will have to fill out the HOA application online through Tenant Evaluation
*Applications must be submitted at least twenty (20) days prior to occupancy / Start of the lease
*Application Fees (Paid by tenant directly) is $250.00 Per Individual age 18 + Over
Property Details
Price:
$9,000
MLS #:
226017428
Status:
Active
Beds:
2
Baths:
2
Type:
Rental
Subtype:
Single Family Residence
Subdivision:
WINDING CYPRESS
Neighborhood:
windingcypress
Listed Date:
Apr 27, 2026
Finished Sq Ft:
1,685
Total Sq Ft:
2,046
Year Built:
2015
See this Listing
Schools
Interior
Appliances
Gas Cooktop, Dishwasher, Disposal, Dryer, Grill – Gas, Microwave, Refrigerator/Freezer, Refrigerator/Icemaker, Self Cleaning Oven, Washer
Bathrooms
2 Full Bathrooms
Cooling
Ceiling Fan(s), Central Electric
Flooring
Carpet, Tile
Heating
Central Electric
Interior Features
Fire Sprinkler, Pantry, Smoke Detectors, Volume Ceiling, Window Coverings
Laundry Features
Laundry in Residence
Levels
1
Exterior
Architectural Style
Ranch, Single Family
Association Amenities
Bike And Jog Path, Bocce Court, Clubhouse, Pool, Community Room, Spa/Hot Tub, Dog Park, Fitness Center, Internet Access, Library, Pickleball, Restaurant, See Remarks, Sidewalk, Streetlight, Tennis Court(s)
Attached Garage YN
1
Community Features
Clubhouse, Pool, Dog Park, Fitness Center, Restaurant, Sidewalks, Street Lights, Tennis Court(s), Gated
Construction Materials
Concrete Block
Covered Spaces
2
Exterior Features
Screened Lanai/Porch
Garage Spaces
2
Other Structures
Tennis Court(s)
Parking Features
2 Assigned, Driveway Paved, Attached
Security Features
Smoke Detector(s), Gated Community, Fire Sprinkler System
Spa Features
Community, Above Ground, Heated Gas, Screened
View
Lake, Landscaped Area
Waterfront Features
Lake
Window Features
Window Coverings
Financial
Map
Community
- Address7052 Live Oak DR NAPLES FL
- SubdivisionWINDING CYPRESS
- CityNAPLES
- CountyLee
- Zip Code34114
Subdivisions in NAPLES
- 291675 – ESPLANADE BY THE ISL PH2
- ACREAGE HEADER
- ARBORETUM A CONDO
- AVERSANA AT HAMMOCK BAY
- BAYVIEW ESTATES
- BRITTANY, THE A CONDO
- FAIRWAYS AT PRCL FOUR-ONE
- FOREST PARK
- FURSE LAKES CLUB
- GLADES COUNTRY CLUB APTS 2,THE
- GOLDEN GATE CITY
- GOLDEN GATE EST UNIT 76
- GOLDEN GATE ESTATE UNIT 1
- GOLDEN GATE ESTATE UNIT 10
- GOLDEN GATE ESTATE UNIT 23
- GOLDEN GATE ESTATE UNIT 26
- GOLDEN GATE ESTATE UNIT 37
- GOLDEN GATE ESTATE UNIT 39
- GOLDEN GATE ESTATE UNIT 40
- GOLDEN GATE ESTATE UNIT 43
- GOLDEN GATE ESTATE UNIT 46
- GOLDEN GATE ESTATE UNIT 59
- GOLDEN GATE ESTATE UNIT 64
- GOLDEN GATE ESTATE UNIT 67
- GOLDEN GATE ESTATE UNIT 70
- GOLDEN GATE ESTATE UNIT 76
- GOLDEN GATE ESTATE UNIT 78
- GOLDEN GATE ESTATE UNIT 79
- GOLDEN GATE ESTATE UNIT 83
- GOLDEN GATE ESTATE UNIT 84
- GOLDEN GATE ESTATE UNIT 86
- GOLDEN GATE ESTATE UNIT 87
- GOLDEN GATE ESTATE UNIT 88
- GOLDEN GATE ESTATE UNIT 89
- GOLDEN GATE ESTATE UNIT 9
- GOLDEN GATE ESTATE UNIT 91
- GOLDEN GATE ESTATE UNIT 92
- GOLDEN GATE ESTATE UNIT 96
- GOLDEN GATE ESTATES
- GOLF COTTAGES WYNDEMERE PH 1&2
- GOODLAND ISLES
- GULF HARBOR
- HUNTINGTON LAKES SIX
- ISLES OF CAPRI UNIT 2
- ISLES/COLLIER PRESERVE PH 17
- KEY ROYAL CONDO
- LAKE PARK
- MARIPOSA AT WHIPPOORWILL
- MILLBROOK FIDDLERS CREEK REPL
- N G & T C L F UNIT 2
- NAPLES MIMOSA CLUB
- NAPLES SANDPIPER BAY CLUB
- NAPLES WINTERPARK NORTH
- ORANGE BLOSSOM RANCH PH 1A
- PALM RIVER ESTATE UNIT 1
- PALM RIVER ESTATE UNIT 5
- PINE RIDGE
- PRESERVE AT THE SHORES
- REGENCY RESERVE A CONDO
- REGENCY WOODS CONDO
- REGENT PARK REP
- ROYAL PALM GOLF ESTATE UNIT 1
- SATURNIA LAKES 1
- STRATFORD PLACE
- TRAIL ACRES
- VALENCIA GOLF & CC PH 2
- VENTURA PH 2
- VILLAGE WALK PH 4
- WILDERNESS COUNTRY CLUB VII
- WILSHIRE LAKES PH 2
- WINDSTAR CONDO SEC
Market Summary
Property Summary
- Located in the WINDING CYPRESS subdivision, 7052 Live Oak DR NAPLES FL is a Rental for sale in NAPLES, FL, 34114. It is listed for $9,000 To schedule a showing of MLS#226017428 at 7052 Live Oak DR in NAPLES, FL, contact your CENTURY 21 Carioti agent at 800-783-8847.
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