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Short Term Rentals in Winding Cypress, FL

25 rentals

7930 Mahogany Run Ln - Photo 1 of 1

11h ago

Our team has verified this company

Verified

7930 Mahogany Run Ln, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,624

$3,404

Price drop

Condo for rent

Top amenities
Air Conditioning
Central Heat
In-Unit Laundry
Microwave
Swimming Pool
Wi-Fi
9159 Delano St - Photo 1 of 1

11h ago

Our team has verified this company

Verified

9159 Delano St, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

3 beds

2.5 baths

$11,775

Condo for rent

Top amenities
Central Heat
Fitness Center
Furnished
Garage Parking
Oven
TV
15140 Pescara St - Photo 1 of 1

11h ago

Our team has verified this company

Verified

15140 Pescara St, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Furnished

3 beds

3 baths

$13,994

Apartment for rent

Top amenities
Central Heat
In-Unit Laundry
Oven
Swimming Pool
TV
Wi-Fi
9155 Delano St - Photo 1 of 1

11h ago

Our team has verified this company

Verified

9155 Delano St, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

3 beds

2 baths

$4,890

House for rent

Top amenities
Air Conditioning
Furnished
Garage Parking
In-Unit Laundry
Microwave
TV
9115 Capistrano St S - Photo 1 of 1

11h ago

Our team has verified this company

Verified

9115 Capistrano St S, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

2 beds

2.5 baths

$3,713

House for rent

Top amenities
Air Conditioning
Central Heat
Fitness Center
In-Unit Laundry
Microwave
Oven
274 Riverwood Rd - Photo 1 of 1
Age restricted

11h ago

Our team has verified this company

Verified

274 Riverwood Rd, Naples, FL 34114

Short term | In-unit laundry | Furnished

2 beds

2 baths

$5,234

Apartment for rent

Top amenities
Central Heat
In-Unit Laundry
Oven
Swimming Pool
TV
Wi-Fi

Nearby rental good for eco-living

$1,500

Naples

Nearby rental good for pet owners

$11,876

Naples

3973 Bishopwood Ct E - Photo 1 of 1

11h ago

Our team has verified this company

Verified

3973 Bishopwood Ct E, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Furnished

3 beds

2 baths

$3,402

House for rent

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
Oven
Wi-Fi
415 Polihale Way - Photo 1 of 1

11h ago

Our team has verified this company

Verified

415 Polihale Way, Naples, FL 34114

Short term | In-unit laundry | Furnished

4 beds

2 baths

$11,876

Apartment for rent

Top amenities
Central Heat
Furnished
In-Unit Laundry
Microwave
Oven
Wi-Fi
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9187 Celeste Dr - Photo 1 of 1

11h ago

Our team has verified this company

Verified

9187 Celeste Dr, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,963

$4,190

Price drop

Condo for rent

Top amenities
Air Conditioning
Central Heat
Dishwasher
In-Unit Laundry
Microwave
Swimming Pool
14632 Edgewater Cir - Photo 1 of 1

11h ago

Our team has verified this company

Verified

14632 Edgewater Cir, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Furnished

2 beds

2 baths

$6,445

Apartment for rent

Top amenities
Assigned Parking
Dishwasher
Garage Parking
In-Unit Laundry
Microwave
Oven
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Find sweet deals near Winding Cypress

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

$4,190

Lely Resort

$8,000

Lely Resort

$4,752

Wentworth Estates

$4,000

Naples

9837 Venezia Cir - Photo 1 of 1

11h ago

Our team has verified this company

Verified

9837 Venezia Cir, Bonita Springs-Naples, FL 34113

Short term | In-unit laundry | Furnished

2 beds

2 baths

$4,752

Condo for rent

Top amenities
Furnished
Garage Parking
Oven
Swimming Pool
TV
Wi-Fi
6726 Sloane Pl - Photo 1 of 1

11h ago

Our team has verified this company

Verified

6726 Sloane Pl, Bonita Springs-Naples, FL 34104

Short term | In-unit laundry | Furnished

3 beds

2 baths

$5,748

Apartment for rent

Top amenities
Assigned Parking
Central Heat
Furnished
In-Unit Laundry
Residents Lounge
Wi-Fi
8036 Belmont Ct - Photo 1 of 1

11h ago

Our team has verified this company

Verified

8036 Belmont Ct, Lely Resort, FL 34113

Short term | In-unit laundry | Furnished

3 beds

2 baths

$5,613

$5,336

Price drop

Apartment for rent

Top amenities
Air Conditioning
Assigned Parking
Central Heat
Dishwasher
In-Unit Laundry
Wi-Fi
Ekos Santa Barbara - Photo 1 of 1
Income restricted

1d ago

7.8

Very good

Ekos Santa Barbara

4640 Santa Barbara Blvd, Naples, FL 34104

Short term

1–3 beds

1–2 baths

$542–$2,229

Apartment for rent

2385 Hidden Lake Dr #10 - Photo 1 of 1

5d+ ago

Short Term condo for rent in Naples

Resort Style Condo In Naples -Largest Pool in Naples

2385 Hidden Lake Dr #10, Naples, FL 34112

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$3,200

Condo for rent

Available Sep 1

Top amenities
Air Conditioning
Garage Parking
In-Unit Laundry
Swimming Pool
14404 Manchester Dr - Photo 1 of 1

5d+ ago

Short Term townhouse for rent in Naples

Furnished Lakeside Resort Villa - SPECIAL MONTHLY RATE MAY TO OCTOBER 2026!

14404 Manchester Dr, Naples, FL 34114

Short term | In-unit laundry | Furnished

3 beds

2 baths

$2,450

House for rent

Available May 1

Top amenities
Air Conditioning
Furnished
In-Unit Laundry
Microwave
On-Site Laundry
Swimming Pool
9060 Michael Cir #12 - Photo 1 of 1

5d+ ago

Short Term Lely Resort condo for rent in Lely Resort

$6,000 - 3 bed 2 bth rental in Lely area of Naples

9060 Michael Cir #12, Lely Resort, FL 34113

Short term | In-unit laundry | Air conditioning

3 beds

2 baths

$6,000

Condo for rent

Available Sep 1

Top amenities
Air Conditioning
Dishwasher
Fitness Center
Garage Parking
In-Unit Laundry
Swimming Pool
15641 Gavello St #NA - Photo 1 of 1

5d+ ago

Short Term Fiddler's Creek house for rent in Bonita Springs-Naples

*NEW* POOL/SPA 3BD+Den 2BA Lakeview w. Resort Amenities

15641 Gavello St #NA, Bonita Springs-Naples, FL 34114

Short term | In-unit laundry | Furnished

3 beds

2 baths

$10,000

House for rent

Available Dec 5

Top amenities
Air Conditioning
Assigned Parking
Dishwasher
In-Unit Laundry
Residents Lounge
Swimming Pool
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15637 Gavello St - Photo 1 of 1

5d+ ago

Short Term Fiddler's Creek house for rent in Bonita Springs-Naples

15637 Gavello St, Bonita Springs-Naples, FL 34114

Short term | Garage parking | Swimming pool

3 beds

2 baths

$3,500

House for rent

Top amenities
Garage Parking
15621 Gavello St - Photo 1 of 1

5d+ ago

Short Term Fiddler's Creek house for rent in Bonita Springs-Naples

15621 Gavello St, Bonita Springs-Naples, FL 34114

Short term | Garage parking | Swimming pool

3 beds

2 baths

$3,500

House for rent

Top amenities
Fitness Center
6816 Sterling Greens Pl ##1105 - Photo 1 of 1

5d+ ago

Short Term Bretonne Park apartment for rent in Bonita Springs-Naples

6816 Sterling Greens Pl ##1105, Bonita Springs-Naples, FL 34104

Short term | On-site laundry | Ceiling fan

2 beds

2 baths

$4,000

Apartment for rent

Top amenities
Ceiling Fan
On-Site Laundry
6641 Alden Woods Circle - Photo 1 of 1

5d+ ago

Short Term Lely Resort house for rent in Lely Resort

6641 Alden Woods Circle, Lely Resort, FL 34113

Short term | Furnished | Swimming pool

3 beds

2 baths

$8,000

House 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

2.5 baths

$3,500

House for rent

Top amenities
Air Conditioning
Ceiling Fan
Fitness Center
In-Unit Laundry
On-Site Laundry
Swimming Pool
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
366 Charlemagne Blvd #C103 - Photo 1 of 1
Age restricted

5d+ ago

Short Term condo for rent in Naples

NEWLY RENOVATED!! 2 Bed/2 Bath Condo (first floor) 55 & OlderCommunity - $2300/month

366 Charlemagne Blvd #C103, Naples, FL 34112

Short term | In-unit laundry | Furnished

2 beds

2 baths

$2,300

Condo for rent

Available Apr 14

Top amenities
Air Conditioning
Carpet
Dishwasher
Hardwood Floor
In-Unit Laundry
Swimming Pool
Showing 1 - 25 of 25 results
Home > Apartments in Verona Walk > Winding Cypress > Winding Cypress Short term rentals
Updated: April 22, 2026

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