Key West 1-2 Bedrooms Homes & Condos Rentals

Are you looking for a 1-2 bedroom rental in Key West, Fl? Last Key Realty has you covered! We have vacation homes that are private homes in the most desirable locations in all of Key West Florida. Whether it is located on Duval St, near Duval Street, 1800 Atlantic, Truman Annex, or a location in the heart of Historic Old Town we have something for everyone. Many of our homes have private pools, full baths, and a front porch for you to enjoy the seasonally warm weather we have year-round. In addition, our homes come fully stocked with all of the appliances, linens, and comforts you can expect in a luxury vacation home in the whole Key West area. Each home is tastefully decorated to show the unique conch flavor of the area.

If you're looking for something smaller, we even have luxurious fully stocked condo rentals in various locations throughout Key West. Our condos have resort-style amenities, including access to onsite pools, spas, tennis courts, and more! Vacation rentals in Key West are our specialty. If you have any questions please feel free to contact one of our vacation specialists today!

2 BEDROOM NIGHTLY/WEEKLY RENTALS

2 BEDROOM MONTHLY RENTALS

54 properties available

SERENITY ON SOUTHARD is a beautifully renovated 1 bedroom second floor condo with a full kitchen and washer and dryer. This condo is located in the Truman Annex, a gated community located in the heart of the island - just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have a peaceful retreat withi

Monthly Rental

A week isn't enough time in Key West! This property is available for longer stays of 29 nights+. Please adhere to calendar months if you can. (Due to strict city ordinances we can't offer it for any less time)

Looking for a month-long stay where you’ll have easy access to the heart of Key West coupled with genuine Old Town charm? Quaint island decor, a cozy space, and a convenient location can all be found in the BARBUDA SUITE at the Seaport Inn. You're just a short walk to the most popular attractions in Old Town and have a comfortable space to duck out

Want to be in the heart of the action but have privacy and seclusion when it’s time to relax? That’s what’s in store for your stay in the CALUSA SUITE at the Seaport Inn! You’ll be miles from reality, but just steps away from the Seaport Inn’s pool and everything else Old Town has to offer. Upon arrival and a walk past the pool, you’ll find your fr

TIDEWATER VIEWS is a cozy 820 square foot cottage that has everything you want for the perfect tropical vacation: open water views from a covered porch, a private 35-foot boat slip, kayaks, bikes and access to the wonderful amenities at Venture Out, a residential community with a heated 80-foot pool with large Jacuzzi and Kiddie Pool, tennis courts

SUITE SANCTUARY is a luxurious penthouse condo that overlooks the ocean and is certain to be your haven from everyday life. This newly renovated condo features many delights throughout, from the vaulted ceilings to the fresh tile floors reminiscent of a walk on the beach. The large balcony offers a place to relax and enjoy the warm Florida weather

HOT 26

25% Off Your Stay!!

Save 25% off on any stay through June 14, 2026 due to construction at the complex! 25% discount is reflected in quoted rate. (FYI - a unit will never be rented while its balcony is being worked on). Call us with any questions.

COLORS OF THE KEYS is a bright and vibrant townhome that embodies Key West’s colorful & tropical spirit. Located within Truman Annex, Key West's most exclusive gated community, this home is within walking distance of all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to a prime location, COLORS OF THE

Monthly Rental

WALKING ON SUNSHINE is a modern, tastefully decorated penthouse condo featuring a large wrap-around balcony that offers a front row seat to those famous Key West sunsets and overlooks the peaceful nature preserve and Atlantic Ocean beyond. Best of all, WALKING ON SUNSHINE is located in an upscale private community within walking or biking distance

HOT 26

25% Off Your Stay!!

Want to be in Key West, have access to all the fun, but not be in the middle of the crowd at the end of the day? Then step away from the hustle and bustle and come roost at… THE OSPREY’S NEST. Boasting views from your private balcony on the top floor of Sunrise Suites, 2-Bedrooms, 2-Bathrooms, and a full kitchen; THE OSPREY’s NEST has all the neces

HOT 25

LA PETITE PENTHOUSE is a jewel-like second-story condo in the Shipyard at the Truman Annex, a gated community located in the very heart of Old Town Key West. You'll be just steps from Mallory Square, Duval Street and all the attractions Key West has to offer. Yet, you'll have all of the peace and quiet that comes with a gated community.THE LIVING A

Monthly Rental

VILLA BAHAMA is located at The Foundry in the Truman Annex, Key West's most exclusive gated community. You'll be just around the block from Mallory Square, Duval Street and all the attractions Key West has to offer, yet you'll benefit from the peace and quiet that the Truman Annex is known for. Smoking is not permitted in any Last Key Realty home.

HOT 27

Monthly Rental

DOLPHIN DAYDREAMS is a freshly built 2-bedroom tropical home specifically designed to be the perfect antidote to the stresses of everyday life. Substitute zoom meetings and rush hour traffic for slow mornings on the patio and afternoons in the sun. Nestled within Venture Out, a popular resort community on Cudjoe Key, this prime location puts you ri

HOT 41

New Property

Don't miss an exceptional opportunity to spend your Key West stay on the grounds of an incredible estate property in the most ideal Old Town location you could imagine. DARLING OF DUVAL is a two-story guest cottage that offers many of the essentials and comforts of a luxury hotel plus the added benefits of an in-home washer & dryer, a private p

HOT 51

Tell us what you're looking for and someone will contact you with available options.

First Name

Last Name

Phone Number

Email Address

Arrival Date

Departure Date

Comments

I agree Sign me up! I agree to receive information about promotional offers and rental info via phone, email or SMS. You can unsubscribe at anytime. Privacy Policy