Windward Breeze

2 Bedrooms 2 Bathrooms Sleeps 4 Key West 1260 sq. ft.

Dive into relaxation at Windward Breeze, a stunning 2-bedroom, 2-bathroom retreat nestled in the heart of Key West. With its prime location in Windward Park, this inviting haven offers breathtaking ocean views and direct access to pristine beaches. Enjoy

Primary Bedroom

1 California King

Downstairs Bedroom

1 King

Windward Breeze is part of the Windward Park gated community just off Simonton Street, one block from Duval Street. There are a total of 13 townhomes in this community that share the 20x50 foot community pool.

Located in a pristine gated community, this 2-bedroom, 2-bath Bahamian-style townhome is surrounded by lush tropical landscaping and views of a sparkling swimming pool. Windward Breeze is located in an ideal area of Old Town Key West. A short stroll to Duval Street offers restaurants, bars, shopping and galleries nearby. Hop on a bicycle and head down to Mallory Square or the Key West Seaport, just a slight distance more. Everything is pretty close on our island. The beaches are also just a short distance from Windward Breeze. 

This spacious vacation home just a block from downtown Key West's famous Duval Street has an open floor plan with lots of space on the main level for relaxing and entertaining. A comfortable seating area with couch and chairs and a flat screen television for those days you want to get out of the sun and just relax. The living area is open to the second floor with high ceilings and plenty of light. 

There is one bedroom on the main level with a full bath. The primary bedroom offers a comfy California king sized bed with ensuite bathroom and flat screen television. We offer all the comforts you need for your stay in paradise including WiFi, flat screen TVs, laundry, lovely and inviting community pool and assigned parking.

This property has a 6 night minimum stay. There is a strict 4 person maximum for this property. DO NOT GO TO THE PROPERTY. Guests must check in at our office at 1075 Duval St Ste C11 to obtain the keys and information.

Tourist Attractions

  • Health Beauty Spa
  • Marinas, Boat Rentals & Excursions
  • Museums
  • Key West Aquarium
  • Public Parks & Beaches
  • Key West Historic Seaport
  • Key West Tropical Forest & Tropical Garden
  • Southernmost Point Buoy
  • Dry Tortugas National Park & Fort Jefferson
  • Fort Zachary Taylor State Park & Beach
  • Sunset Celebration at Mallory Square
  • History Tours - Motorized, Walking & Biking
  • The Florida Reef - N. America’s only living coral barrier reef
  • Key West Marine Park stretching from Higgs Beach to South Beach
  • The Key West Butterfly & Nature Conservatory
  • Food Tours
  • Ghost Tours
  • Pub Crawls
  • Your reservation guest portal will provide details

Accommodation Essentials

  • Hair Dryer
  • Hangers
  • Kitchen
  • Shampoo
  • Wireless Internet
  • Body Wash
  • Air Conditioning
  • Bed Linens
  • Cable
  • Towels
  • Hot Water
  • Dryer
  • Essentials
  • Living Room
  • Parking
  • Iron & Ironing Board
  • Washer

Sports

  • Paddle Boarding
  • Fishing - Surf
  • Hiking
  • Banana Boat Riding & Water Tubing
  • Wind Surfing
  • Ocean Waterpark & Challenge Course
  • Kayaking
  • Kite Boarding
  • Pickleball
  • Tennis
  • Golfing
  • Scuba Diving
  • Skydiving
  • Your reservation guest portal will provide details
  • Cycling
  • DeepSea Fishing
  • Fishing - Backcountry
  • Jet Skiing
  • Para-sailing
  • Fishing - Pier
  • Sailing
  • Snorkeling
  • Swimming

Leisure

  • Dolphin Watching
  • Dining Out
  • Live Theater, Concerts & Entertainment
  • Your reservation guest portal will provide details
  • Paint & Sip Art Classes
  • Bird Watching
  • Boating
  • Eco Tourism
  • Shopping

Local

  • Banks
  • Grocery Stores
  • Fitness Centers
  • Hospital
  • Laundromats

Kitchen

  • Coffee Maker - Drip
  • Dishes & Silverware
  • Microwave
  • Refrigerator
  • Toaster
  • Stove
  • Dishwasher
  • Oven

Home Safety

  • Fire Extinguisher
  • Smoke Detector

Car

  • Not Necessary

Entertainment

  • Satellite or Cable
  • Television
  • Smart TV

Facility

  • Free Parking
  • Pool

Outdoor

  • Garden or Backyard
  • Balcony
  • Deck Patio Uncovered
  • Grill

Location

  • Historic District
  • Village

Pool

  • Communal Pool

Themes

  • Family
  • Historic
  • Romantic
  • Tourist Attractions
LEAVE A REVIEW
February 15, 2026 - Track Survey

by Steve S

Excellent townhouse

January 26, 2026 - Track Survey

by Peter C

Thanks for another great trip. Great location! Fantastic house. Always like having you folks not cheap out on one roll of TP, laundry and dishwasher detergent 🙂

January 1, 2026 - Track Survey

by David H

Everything was wonderful

October 27, 2025 - Track Survey

by Emma S

Great rental. Very good location, great pool and quaint community village. The rental was very clean. Will book again.

July 9, 2025 - Track Survey

by Jonathan M

Beautiful home, close to everything, convenient check in/out

June 2, 2025 - VRBO

Great pad

by Sam D

Beautiful place great location.

January 21, 2025 - Track Survey

Perfect house for traveling couples

by Sunnee C

The townhome is the perfect house for traveling couples. We will rent it again.

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