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As Neptune was known as the Roman God of the Sea, NEPTUNE'S PENTHOUSE is known as the crown jewel of the 1800 Atlantic complex overlooking the Sea. This Penthouse Condominium has a lavish wrap-around balcony that overlooks the Atlantic Ocean and Community Pool below. You'll be able to enjoy the refreshing Key West breezes from atop your own private
Neptune's Penthouse
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (277)
THE COZY STARFISH is a newly furnished and decorated first floor condo located in the Truman Annex, a private gated community situated in the heart of the island. Despite being only steps away from all that Old Town Key West has to offer, THE COZY STARFISH is a peaceful retreat within a private gated community that offers access to a large, shared
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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)
The Cozy Starfish
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating Rating Rating Rating Rating 5 (13)
FOLLOW THE SUN is located at 1800 Atlantic Blvd on the beach, with sunset views right from your own 28-foot balcony. You'll be able to enjoy quiet afternoons with those balmy Key West breezes wafting through the floor-to-ceiling glass doors. FOLLOW THE SUN is located in an upscale private community within walking or biking distance to all of your f
Follow the Sun
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (256)
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 Monthly Rental
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)
Serenity on Southard
Condo
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating Rating Rating Rating Rating 5 (57)
GULFSIDE VISTAS is a beautiful penthouse condo and is the perfect place to spend your stay in Key West, with panoramic views of the Gulf and cruise ships as they dock nearby. You'll have ocean views on three sides of GULFSIDE VISTAS, and two spacious balconies as well.Compliance with Truman Annex Community Rules & Regulations is expected of all
Monthly Rental Monthly Rental
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)
Gulfside Vistas
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (271)
The moment you arrive at CASA AMARILLA and see the dual rocking chairs beckoning you to the front porch, you’ll feel the weight of the world start to lift from your shoulders as your vacation truly begins. Upon entering this adorable cottage, you’ll see the quaint interior is the perfect place to unwind, offering cozy bedrooms, a fully stocked kitc
Hot HOT 28
Casa Amarilla
Private Home Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (161)
SUZY'S PARROT PERCH is a charming apartment that is located in the heart of Old Town on the corner of two historic streets (Whitehead and Virginia) just steps from Duval and two blocks from the Southernmost Point. You couldn't be any closer to the nightlife and attractions on Duval Street (Flamingo Crossing, the famous homemade Key West ice cream p
Suzy's Parrot Perch
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (386)
Hidden amongst the thick of Old Town Key West, within Truman Annex, Key West's most exclusive gated community, lives a 'gem' of a home that will surely capture your heart's desire from the moment you lay eyes on it. JASMINE JEWEL is a two-story private home that not only transcends island living at its finest but also offers an ideal location for e
Monthly Rental Monthly Rental
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)
Jasmine Jewel
Private Home
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (107)
ATLANTIC REFLECTIONS is a newly renovated water view condo that has been meticulously furnished with a modern tropical feel, with spectacular views of the neighboring nature preserve and the ocean beyond, with no end in sight. You'll be able to enjoy those famous Key West sunsets from the living room, and sunrise shadows from your bedroom balconies
Atlantic Reflections
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (255)
This Old Town condo is perfect for anyone who can't get enough of Key West's famous nightlife scene. CASITA ANGELITA is located right in Old Town, half a block away from Duval Street and smack dab in the center of the entertainment district. You couldn't be any closer to the late-night scene and attractions of downtown. Fair warning... It can get
Casita Angelita
Condo Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (296)
Located across the street from Blue Heaven, above the delicious La Creperie French Cafe, sits THE PIRATE’S PENTHOUSE. This hidden gem is ideally located in the heart of Bahama Village and within walking distance to everything Duval has to offer. THE PIRATE’S PENTHOUSE has touches of maritime decor sprinkled throughout this spacious condo, complete
The Pirate's Penthouse
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (76)
TURTLE COVE VIEWS is a cozy waterfront cottage that provides a picturesque Florida Keys vacation setting. Take in the expansive open water views from inside the home through the large windows or from your covered porch, with outdoor dining. The private 35-foot boat slip offers easy access to the beautiful waters of the Florida Keys and the home com
Turtle Cove Views
Cottage Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating Rating Rating Rating 4.9 (183)

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