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2 Bedroom Key West Rentals

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Valhalla

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

This two-bedroom, two-bath classic contemporary is the perfect headquarters for your dream vacation. The entire inside is painted cloud white. This choice creates not only a crisp, clean elegance but also serves as the perfect backdrop for an amazing art collection. It's fitting that this special...

Quilted Giraffe

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Your space. Your vacation lifestyle. The Quilted Giraffe provides both. This two-bedroom, two full bath home welcomes you from its quiet neighborly front porch facing tree-lined Elizabeth street to its private deck and heated pool in the rear. The location called Solares Hill is a part...

Duval Square

Nightly and Weekly Rentals
2 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

There's no more perfect place to practice the art of tropical vacationing than this professionally decorated, two-story townhome, which features two bedrooms, two and a half baths, a private deck with private hot tub, and a master bedroom balcony. A short walkway flanked by lush gardens...

Banana Key

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED RATES for Open Dates this SUMMER!

Impressive. Distinctive. Comfortable. The perfect spot for your tropical getaway. This second-story, two-bedroom, two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area one floor below, you can...

Havana Hideaway

Nightly and Weekly Rentals
2 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

Call it casual luxury. Call it tropical chic. This two bedroom/two full bath Harbour Place condominium is a part of Key West's prestigious Truman Annex community. From the luxurious pool area below, you can enjoy breathtaking views just steps from the Gulf of Mexico. Watch passing...

Duval Street Suite

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

It's all about location: in this case, a dream vacation location in the heart of Old Town Key West. Duval Street Suite is a two-bedroom, two-full-bath townhouse in a small rooftop community overlooking the island's main artery for fun and entertainment.

From your private and...

The Meadows House

Nightly and Weekly Rentals
2 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 4
Max Occupancy 6

If you choose this two-bedroom, two plus bath home for your Key West vacation, you won't be sorry. While Key West has some fourteen neighborhoods, locals identify The Meadows area, your vacation neighborhood, as the most neighborly. Here you'll find houses with a statistically high year-around...

La Prive

Nightly and Weekly Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

DISCOUNTED RATES for Open Dates this SUMMER!

This is the real deal-a light, airy, well-appointed Key West townhome with two stories, two bedrooms, two full baths, and all the amenities needed to enhance your vacation lifestyle. Not to mention a large private deck and an inviting...

Royal Palm

Nightly and Weekly Rentals
2 Bedrooms
2.5 Bathrooms
Comfortably Sleeps 4
Max Occupancy 5

DISCOUNTED RATES for Open Dates this SUMMER!

There's no better way to experience "Island Time"-that slow shifting of hours that makes Key West such an ideal vacation spot-than staying at Royal Palm. Located in the prestigious Foundry building within the exclusive Truman Annex gated community, this...

Shipyard

Nightly and Weekly Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

(The Shipyard Owners Association has informed us that the parking area will be closed AUGUST 20 - 31st 2018 for repaving (subject to change) so there will be no parking available during this period. If you wish to book during this time frame please contact our...

La Hacienda

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Looking as though it were plucked from the glossy pages of Spanish literature, La Hacienda is one of Key West's most distinctive two bedroom/two bath homes. Located on fashionable Southard Street in the heart of Old Town, the first thing you notice as you arrive is...

En Plein Air

Monthly and Seasonal Rentals
2 Bedrooms
1.5 Bathrooms
Comfortably Sleeps 2
Max Occupancy 4

En Plein Air is a property that was purchased by the owners for its heritage and natural light. An artist lives here in this former general store. Recently renovated, it remains sympathetic to its 1880s roots. All the rooms have ceiling fans and air conditioners. Modern...

Anne's Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

For luxurious vacation living, dining, sleeping, and playing, this historic Conch Home on fashionable Southard Street in the heart of Old Town hits the bullseye. It has been totally renovated, keeping its original cottage essence while adding contemporary design updates and modern functionality. The pool and...

Ananas

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

The pineapple-or ananas as it's known by its genus name-is the classic symbol of hospitality. This two bedroom, two full bath conch house, aptly named Ananas, is truly the embodiment of warm, welcoming hospitality. Its location, style, and comfort reward the lucky visitors who choose to...

Conch Clubhouse

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 4
Max Occupancy 4

Six French doors dominate the architectural design of this classic two bedroom/two full bath conch style home. What better place for letting in all that ambient light and breeziness than sunny Key West, where balmy weather and crystal blue skies are the norm. If you happen...

Azure Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
2 Bathrooms
Comfortably Sleeps 6
Max Occupancy 8

So you've decided to become one of those lucky enough to be vacationing in extraordinary Key West this year! Your next step is to choose just the right residence. With two plus bedrooms, two full baths, and a stellar location, Azure Hideaway could easily be your...

Hilltop Hideaway

Monthly and Seasonal Rentals
2 Bedrooms
1 Bathroom
Comfortably Sleeps 4
Max Occupancy 4

Hilltop Hideaway is near the top of Solares Hill, the highest point in Key West, a mere 15 feet above sea level. ("Hilltop" is a word the locals use loosely in Key West!) This meticulously cared for two-bedroom, one full bath condo is near the center...