Monthly Rentals in Windley Key

Discover long-term rentals that feel like home for stays of a month or longer.

Nearby monthly rentals

Guest favorite

A resort-style swimming pool is surrounded by lush palm trees, offering a relaxing atmosphere. Comfortable lounge chairs are positioned around the pool, with tranquil ocean views in the background. Clear blue skies complement the serene setting, suggesting an inviting space for leisure.

Home in Islamorada

5 out of 5 average rating, 20 reviews

Pristine pool front home w/ocean views Anglers 148

Guest favorite

A covered balcony offers ocean views and features a stylish, woven chair. Bright blue skies and calm waters add to the serene atmosphere, while white railings complement the coastal architecture.

Home in Islamorada

5 out of 5 average rating, 15 reviews

TheSandbar: Oceanfront,Pool,Free Dockage,Gameroom

Guest favorite

A two-story structure with a light-colored exterior is framed by well-maintained greenery. The front porch features a railing and is flanked by palm trees, creating a welcoming entrance. Large windows allow natural light to enter the home.

Villa in Islamorada

4.9 out of 5 average rating, 21 reviews

Islamorada house with best location. Lic # 24-0055

Top guest favorite

Home in Islamorada

5 out of 5 average rating, 7 reviews

OceanView Private Beach Pool Islamorada w/ Marina

The comforts of home and great monthly rates

Fully furnished rentals

From peaceful mountain cabins to convenient urban apartments these furnished rentals have all the amenities of home.

Digital nomads & traveling professionals

Comfortable accommodations for nomadic and remote working professionals with wifi and dedicated work spaces.

Delight included

Sometimes the destination is the accommodation. From cliffside cabins to tranquil houseboats, these rentals are full of unique features.

Pets welcome

Discover places to stay that accommodate pets, so you can bring your four-legged friend along.

Amenities and perks for longer stays

Furnished rentals

Fully furnished rentals include a kitchen and the amenities you need to live comfortably for a month or longer. It’s the perfect alternative to a sublet.

Flexibility you need

Choose your exact move-in and move-out dates and easily book online, without any additional commitment or paperwork.*

Simple monthly prices

Special rates for long-term vacation rentals and a single monthly payment without additional charges.*

Book with confidence

Reviewed by our trusted community of guests and 24/7 support during your extended stay.

Work-friendly spaces for digital nomads

Traveling professional? Find a long-term stay with high-speed wifi and dedicated working spaces.

Looking for corporate housing?

Airbnb has fully furnished apartment homes ideal for staffing, corporate housing, and relocation needs.

Popular amenities for monthly rentals

Kitchen

Wifi

Pet friendly

Laptop-friendly workspace

Free parking on premises

Corporate Housing

Destinations to explore

*Some exclusions may apply in certain geographies and for some properties.