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Short Term Rentals in Winding Cypress, FL

25 rentals

1501 Chesapeake Ave - Photo 1 of 1

7h ago

Our team has verified this company

Verified

1501 Chesapeake Ave, Naples, FL 34102

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,200

Condo for rent

Top amenities
Central Heat
Furnished
In-Unit Laundry
Oven
Storage
TV
3410 Seminole Ave - Photo 1 of 1

7h ago

Our team has verified this company

Verified

3410 Seminole Ave, Naples, FL 34112

Short term | In-unit laundry | Furnished

4 beds

3 baths

$7,704

Apartment for rent

Top amenities
Air Conditioning
Garage Parking
In-Unit Laundry
Microwave
Swimming Pool
TV
149 Beachcomber St - Photo 1 of 1

7h ago

Our team has verified this company

Verified

149 Beachcomber St, Marco Island, FL 34145

Short term | In-unit laundry | Furnished

2 beds

2 baths

$22,385

$17,040

Price drop

Apartment for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
Swimming Pool
TV
3100 Andrews Ave - Photo 1 of 1

7h ago

Our team has verified this company

Verified

3100 Andrews Ave, Naples, FL 34112

Short term | In-unit laundry | Furnished

3 beds

1 bath

$4,606

$4,366

Price drop

Apartment for rent

Top amenities
Central Heat
Furnished
In-Unit Laundry
Microwave
On-Site Management
Wi-Fi
Ekos Santa Barbara - Photo 1 of 1

3d ago

8.3

Very good

Ekos Santa Barbara

4640 Santa Barbara Blvd, Naples, FL 34104

Short term

1–3 beds

1–2 baths

$1,181–$2,229

Price drop

Apartment for rent

3325 Airport Rd N ##G2 - Photo 1 of 1

3d ago

Short Term apartment for rent in Naples

3325 Airport Rd N ##G2, Naples, FL 34105

Short term | On-site laundry | Swimming pool

2 beds

1 bath

$1,585

Apartment for rent

Top amenities
On-Site Laundry

Nearby rental good for eco-living

$4,499

Naples

Nearby rental good for pet owners

$4,200

Royal Harbor

14384 Tuscany Pointe Cv #NA - Photo 1 of 1

3d ago

Short Term house for rent in Naples

14384 Tuscany Pointe Cv #NA, Naples, FL 34120

Short term | In-unit laundry | Furnished

4 beds

2 baths

$4,500

House for rent

Available Nov 1

Top amenities
Air Conditioning
Assigned Parking
Dishwasher
In-Unit Laundry
Swimming Pool
Wi-Fi
6626 Alden Woods Cir - Photo 1 of 1

5d+ ago

Short Term Lely Resort house for rent in Lely Resort

Short term | Garage parking | Swimming pool

2 beds

2 baths

$8,000

House for rent

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7034 Saona Ct - Photo 1 of 1
New construction

5d+ ago

Short Term Sabal Bay apartment for rent in Bonita Springs-Naples

7034 Saona Ct, Bonita Springs-Naples, FL 34113

Short term | Garage parking | Swimming pool

2 beds

2 baths

$6,800

Apartment for rent

Top amenities
Hardwood Floor
170 Turtle Lake Ct #103 - Photo 1 of 1

5d+ ago

Short Term condo for rent in Naples

Central Naples Condo

170 Turtle Lake Ct #103, Naples, FL 34105

Short term | Furnished | Air conditioning

2 beds

2 baths

$2,800

Condo for rent

Available Nov 27

Top amenities
Assigned Parking
Fitness Center
Furnished
Hardwood Floor
On-Site Laundry
Wheelchair Accessible
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Find sweet deals near Winding Cypress

These rentals are 10%-30% cheaper than the local average price for similar rentals.

$8,000

Lely Resort

$4,000

Naples

$2,350

Whippoorwill

$3,531

Old Naples

14582 Edgewater Cir #NA - Photo 1 of 1

5d+ ago

Our team has verified this company

Verified

14582 Edgewater Cir #NA, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Air conditioning

2 beds

2 baths

$7,000

House for rent

Available Oct 3

Top amenities
Assigned Parking
Dishwasher
Fitness Center
Hot Tub
In-Unit Laundry
Swimming Pool
14265 Laguna Springs Ln #NA - Photo 1 of 1

5d+ ago

Short Term Naples Reserve Golf Club house for rent in Bonita Springs-Naples

Pool/Spa Lakeview STOCK Custom Home 4 Bed 3 Bath

14265 Laguna Springs Ln #NA, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Air conditioning

4 beds

3 baths

$13,000

House for rent

Available Nov 23

Top amenities
Air Conditioning
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
Swimming Pool
1701 Gulfstar Dr S - Photo 1 of 1

5d+ ago

Short Term condo for rent in Naples

1701 Gulfstar Dr S, Naples, FL 34112

Short term | In-unit laundry | Furnished

3 beds

3 baths

$10,000

Condo for rent

Available Nov 1

Top amenities
Air Conditioning
Dishwasher
Furnished
High Ceilings
In-Unit Laundry
Swimming Pool
6562 Amarone Ln - Photo 1 of 1

5d+ ago

Short Term Lely Resort house for rent in Lely Resort

6562 Amarone Ln, Lely Resort, FL 34113

Short term | Furnished | Swimming pool

3 beds

3 baths

$15,000

House for rent

7966 Haven Dr #19-01 - Photo 1 of 1

5d+ ago

Short Term condo for rent in Naples

Fully Furnished & Stocked Paired Villa 2 Bed/2 Bath + Den

7966 Haven Dr #19-01, Naples, FL 34104

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,499

Condo for rent

Available Jan 1

Top amenities
Air Conditioning
Fitness Center
Garage Parking
In-Unit Laundry
On-Site Management
Swimming Pool
293 Kings Way - Photo 1 of 1

5d+ ago

Short Term Foxfire house for rent in Bonita Springs-Naples

Short term | Swimming pool | Ceiling fan

2 beds

2 baths

$8,000

House for rent

Top amenities
Tile Floor
6225 Bellerive Ave ##1504 - Photo 1 of 1

5d+ ago

Short Term Vineyards condo for rent in Vineyards

6225 Bellerive Ave ##1504, Vineyards, FL 34119

Short term | Swimming pool | Ceiling fan

3 beds

2 baths

$6,000

Condo for rent

Top amenities
Tile Floor
600 Squire Cir - Photo 1 of 1

5d+ ago

Short Term Berkshire Lakes condo for rent in Bonita Springs-Naples

Short term | On-site laundry | Swimming pool

2 beds

2 baths

$2,200

Condo for rent

Top amenities
On-Site Laundry
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6641 Alden Woods Cir - Photo 1 of 1

5d+ ago

Short Term Lely Resort house for rent in Lely Resort

6641 Alden Woods Cir, Lely Resort, FL 34113

Short term | Furnished | Swimming pool

3 beds

2 baths

$8,000

House for rent

4621 Bayshore Dr Apt Q4 - Photo 1 of 1

5d+ ago

Short Term condo for rent in Naples

4621 Bayshore Dr Apt Q4, Naples, FL 34112

Short term | Ceiling fan | Outdoor space

2 beds

2 baths

$1,700

Condo for rent

9072 Covina Dr N ##5505 - Photo 1 of 1

5d+ ago

Short Term Lely Resort townhouse for rent in Lely Resort

9072 Covina Dr N ##5505, Lely Resort, FL 34113

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$3,500

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Fitness Center
In-Unit Laundry
On-Site Laundry
Swimming Pool
14651 Topsail Dr #NA - Photo 1 of 1

5d+ ago

Short Term Naples Reserve Golf Club house for rent in Bonita Springs-Naples

14651 Topsail Dr #NA, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Furnished

4 beds

2 baths

$10,000

House for rent

Available Jul 1

Top amenities
Air Conditioning
Assigned Parking
Furnished
Hot Tub
In-Unit Laundry
Swimming Pool
1004 Hampton Cir - Photo 1 of 1

5d+ ago

Short Term Whippoorwill townhouse for rent in Bonita Springs-Naples

1004 Hampton Cir, Bonita Springs-Naples, FL 34105

Short term | Garage parking | On-site laundry

3 beds

2 baths

$2,350

House for rent

Top amenities
Ceiling Fan
On-Site Laundry
5515 Rattlesnake Hammock Rd ##205 - Photo 1 of 1
Age restricted

5d+ ago

Short Term apartment for rent in Naples

5515 Rattlesnake Hammock Rd ##205, Naples, FL 34113

Short term | Swimming pool | Elevator

2 beds

2 baths

$4,000

Apartment for rent

Top amenities
Tile Floor

5d+ ago

Short Term apartment for rent in Marco Island

10 Tampa Pl, Marco Island, FL 34145

Short term | Swimming pool

1 bed

2 baths

$7,500

Apartment for rent

Showing 1 - 25 of 25 results
Home > Apartments in Verona Walk > Winding Cypress > Winding Cypress Short term rentals
Updated: October 20, 2025

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🔑Available apartment rentals25
💰Best rent deal4640 Santa Barbara Blvd
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