Villa vacation rentals in Stock Island

Howard House on the Sea

Oceanfront coastal elegant 10.5 feet from door to ocean with an extraordinary, unobstructed view of sunrises. Dock your 30’ boat here. Designed to make you feel like it’s your home from the minute you walk in the door. Fresh,clean and fabulously landscaped. Gourmet kitchen. Kayaks. Pool. Hot tub, tennis/pickle ball courts, washer/dryer, high speed internet and smart TV. Only 20 minutes north of key west. Fish off the dock! $100 gift card to Square Grouper or Broils for 7 or more night stay

Beachfront • Heated Pool • Hot Tub • Oceanview

Welcome to Colson Cudjoe Key 916 by LuxuryLodgingSTR, the name guests can easily remember when planning their stay. Welcome to your slice of paradise in Cudjoe Key! This two-story Oceanview villa combines tropical serenity with modern comfort, perfect for families, couples, or friends. Enjoy a private heated pool and spa, spacious living areas, and breathtaking Atlantic views from the master suite.

Pilar House Key West

Beautiful townhouse in the heart of Key West. Three bedrooms, a bright living room, a cozy kitchen, and a private deck. Perfectly located for exploring Old Town—Pilar House sits steps from top attractions. Just one corner from iconic Sloppy Joe’s and the Duval Loop stop on Caroline Street, offering free and easy rides around the island.

Coral Palm by AvantStay | Mins From DT Key West

- Shared Pool - Located in the private gated community - >5 miles from downtown Key West - Private porch & outdoor dining space