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  • (305) 294-7358
Key West Time
April 23rd
6:53am · 73°F

Ocean View Luxury Villa ~ Weekly Rental

3BR 4BA ~ Weekly Rental
Sleeps 6-8

If you've been searching for a Key West ocean view luxury home, this could be the place for you. You've probably learned that nearly all water-view vacation rental properties on Key West are hotels, condominiums, or time-shares. But this place is a rare exception to this rule. Ocean View Luxury Villa, offers both an open water view and easy beach access! Situated next to Key West’s very best beach, Fort Zachary Taylor, this Key West beach house is also only a few short walking streets from the heart of downtown Old Town.

Holding an enviable spot in Old Town Key West's up-scale gated community named "Truman Annex," this charm-charged historic neighborhood was named for President Harry Truman who spent his winters here, at his presidential home known as "The Little White House." His famous residence is now a museum and if you look on a map you'll see it's just a short walk from this luxury Key West vacation rental we call Ocean View Luxury Villa.

Fashionably tucked behind a white picket fence on a quiet cal-de-sac street, this "beach-style" vacation house combines island living with luxury and minimalism in precisely the right way. Drawing from classic Key West architecture, everything about this property celebrates authentic Key West island life in a casual yet up-scale style. Wide sitting porches with white picket railings, capital topped porch posts, sash hung windows, French doors, and a shiny tin roof all reflect the essence of island charm. Traditional wooden siding painted white with dark green shutters and haint blue porch ceilings, creates a story-book scene framed by tropical landscaping and tall palm trees living around the property.

Interior Layout

1st Floor: Upon entering from the front porch, the open concept floorplan and high ceilings create a grand feeling while remaining casual and far from pretentious. Three sets of 15 paned French doors along the back wall invite in the sunlight from the beach side, whilst creating an impressive entrance to a screened in porch and the back yard pool garden. Tropical and maritime furnishings of light wood and wicker include an overstuffed sofa, chaise, and easy chair further the casual yet elegant beach house feeling. Sand-tone Mexican floor tiles throughout provides natural cooling and furthers the feeling of spaciousness. One can immediately see the potential for hosting family gatherings and sharing meals furthered by the non-excluding open concept.

On your immediate left, as you enter the front door, a large glass L-shaped desk satisfies the necessity for a business station should you need to catch up on work during your stay. Behind it, along the back wall, the entertainment center is set slightly back in an octagon alcove, creating the feeling of a separate media room.  Complete with recliner sofas, sound system, cable and internet, your whole group can comfortably enjoy a movie night or video games.

The spacious kitchen is set to the right of the room, toward the back corner. It has traditional wood and Formica cabinetry and large countertops, built in a unique stylized circular shape that is reminiscent of a galley of a large luxury motor yacht. Fully equipped, there is plenty of prep and serving space for the serious cook, and the openness allows the meal maker to enjoy the company of everyone without ever having to leave the kitchen.  A glass top dining table for six is conveniently placed in the center of the room, adjacent to the kitchen, between the breakfast bar and the media room. However, our bet is that dining al-fresco at the outdoor dining set placed on the covered porch, will be a favorite eating gathering place. 

Notice that next to the kitchen counter, the side door entryway to the carport that allows easy access for grocery runs. Along the way you’ll see the door to the 1st floor full bathroom with a walk-in shower, ideally situated for after a swim in the pool. Then, on the right of the front door, a beautiful hardwood banister staircase with white trim leads to the upper floors.  But before we head up there, notice the lounge chair that sits kitty-corner in front of the hidden laundry closet. This washroom provides a high-end large-load washer and dryer to fill any family laundry needs.

2nd Floor: The staircase makes its way to the 2nd floor with one platform stop, and then a switch-back turn to reach two bedrooms, each with an en-suite bathroom. At the top of the landing, both bedrooms are straight ahead. Each bedroom suite is softly decorated with tropical colors referencing the ocean, and accentuates the relaxing vibe the home emits.  Wicker furniture in both bedrooms continues the island theme, and the color scheme remains cool, and calming. To the right, the guest bedroom suite is painted blue, and offers two full sized bed. The bathroom offers a shower. The master bedroom done in yellow and green tones is on the left. It is comfortably furnished with a king size bed, white cushioned sofa chairs, and a European size refrigerator. The spacious master bath offers a bathtub with in-tub shower. A bonus feature of each of the 2nd floor en- suite bathrooms, are private doors that lead to the 2nd floor porch expanding the entire length of the front of the house. How nice to step outside for a breath of tropical air after a nice soothing shower.

More outdoor space on the 2nd floor is found on the covered balcony that runs along the entire back of the house and connects with each bedroom through separate double French doors. It is here where we get our first glimpse of the ocean and the docks below. An added architectural feature of the porch, are two stairways on either side of the balcony. These stairways lead to the 1st floor screened porch, providing outdoor exits (and entrances) from the bedroom suites. But before we go back downstairs to the pool, let’s continue up to the 3rd floor. It is here where we capture the best ocean view in the house.

3rd Floor: You may have to flip a coin to see who gets to sleep in this special space, the loft-style 3rd floor bedroom plus viewing deck. A switch back railed staircase takes you up there, and at the landing you see that you’re in a completely different scene from the rest of the house. Like a captains private quarters on a modern sea faring vessel, the full size bed is neatly tucked into a sleeping nook. Across the room is a spacious porch with a command view of the sea and of course those famous Key West sunsets. Of course, the rest of your clan will also come up here to catch the ocean breezes and the sky, but that’s on the opposite end of the room from the sleeping quarters. Hardwood floors,

Key lime green walls, bright white trim, ceilings with recessed lighting, keep this top-of-the-house room light and airy. A small tiled bathroom with a pedestal sink and walk in shower makes it all the more comfortable and convenient. And, it you find watching the ocean scene and docks to be a favorite source for entertainment, there’s also a microwave up here if you decide to make popcorn or maybe some bedtime tea.

Exterior Porches: One of the most desirable features of this ocean view property is the extensive outdoor porch spaces. The house boasts 1st and 2nd floor porches, both front and back, and the private porch on the 3rd floor is a sunbathers dream. The first floor front porch has a charming porch swing for two, creating a romantic setting for sharing a glass of wine and maybe stealing a kiss.

1st Floor: The back porch of the first floor has full screens so the outdoor dining table can remain pest free.  A spiral staircase allows easy access between the three back porches and adds an elegant twist on the tropical back yard.  The tiled floor of the 1st floor back porch, coupled with the three sets of French doors, permits the porch to be an extension of the first floor when open.  Outdoor speakers, patio furniture, and a ceiling fan, make it the exemplary island-entertainment space.

2nd Floor: The master and guest bedrooms of the second floor are connected through their shared porch on both the front and back of the house. Also completely furnished, there is no lack of outside relaxing space. The elevation also provides a great view over the backyard out onto the ocean.

3rd Floor: From the third bedroom, the ideal sunbathers’ porch with recliner seats can be accessed. A private space with scenic view makes for optimal sunbathing and sunset viewing.

Grounds: One of the best parts of living in Key West is the indoor-outdoor lifestyle. The back yard of the Ocean View Luxury Villa, is the highlight of the fun, and will keep you entertained outside on multiple levels with beautiful views front and back. An expansive wood deck and large swimming pool make any day spectacular.  Lounge chairs, a hammock, outdoor dining table and landscaping provide a tropical island feel while still creating the privacy anyone would desire. Grills, pool toys, and plenty of room facilitate the fun possibilities as extensive as your imagination.

Neighborhood grounds throughout the gated Truman Annex complex are park-like, exquisitely landscaped and manicured to picturesque perfection, making it a delightful neighborhood to walk and bicycle. White picket fences, freshly clipped hedges, green grounds and fountains create an impressive back drop for your stroll around this unique neighborhood. Original military officer's homes that display romantic classic Italian and Greek revival architectural styles have been renovated into large private luxury mansions. Just out the gate towards the ocean, is Fort Zachary Taylor State Park, considered the nicest beach on Key West. You’re also just a few minute walk to Duval St. and the center of downtown Old Town Key West.

This property is offered as an exclusive vacation rental in Old Town Key West. This is a smoke free house. The Truman Annex residential location has neighborhood association rules, and is definitely not suitable for staging loud parties. This property is not "child-proof." We do not accept guests less than 25 years of age unless accompanied by a family group or guardian. 

Bedding Summary:

  • 2nd Floor - 1 King size bed; 2 Full size beds;
  • 3rd Floor - 1 Full (double) size bed

Amenities: Stunning open water view of Gulf of Mexico with large private sunning deck. Private back yard, small swimming pool with waterfall, lush tropical landscaping. Master bedroom opens to pool patio. Designer furnished, fully equipped kitchen, Central air conditioning, washer / dryer, Audio Visual Systems, DSL Internet, and HD TV.

Activities: Short walk to all old town features. 10 to 15 stroll to Mallory Square. Just a few short streets from Duval St. Short walk to Fort Zachary Taylor State Park Beach and Truman Waterfront Park and Key West Amphitheater.  Close to boutique shopping, art galleries, and a variety of national and international restaurants, coffee shops. Close to the beach. You can get everywhere in Old Town on foot in a short time (remember - it takes 3 to 4 Key West streets to make a city block). Colorful and historic Bahama Village is just outside the main front gate, and home to a delightful variety of cool and funky cafes and restaurants.

Area: Located in Truman Annex luxury gated neighborhood steps away from all Key West Old Town features. Grounds throughout the gated Truman Annex complex are park-like - exquisitely landscaped and manicured to picturesque perfection, making it a delightful neighborhood to walk and bicycle. From here you are just a few minutes walk to Duval St. and the center of downtown Old Town Key West. White picket fences, freshly clipped hedges, green grounds and fountains create an impressive back drop for your stroll around this unique neighborhood. Original military officer's homes that display romantic classic Italian and Greek Revival architectural styles have been renovated into large private luxury mansions. Just out the gate towards the ocean is Fort Zachary Taylor, now a State Park with one of the nicest beaches on Key West.

Parking: Parking available in the driveway next to the house. Please ask about the availability of additional off-street covered parking. However, from this location you do not need a car. Enjoy walking or biking everywhere-you'll see more that way.

Restrictions: No Pets, please. SMOKE FREE. Absolutely No Smoking on the premises! 



Book Direct For The Best Price Guaranteed

Dates Weekly Nightly Terms
Apr 13, 2024 - May 29, 2024 $8158$1165.007 night minimum
May 30, 2024 - Jun 9, 2024 $8158$1165.007 night minimum
Jun 10, 2024 - Aug 11, 2024 $8158$1165.007 night minimum
Aug 12, 2024 - Oct 2, 2024 $8158$1165.007 night minimum
Oct 3, 2024 - Oct 17, 2024 $8158$1165.007 night minimum
Oct 18, 2024 - Oct 27, 2024 $10740$1534.007 night minimum
Oct 28, 2024 - Nov 3, 2024 $8158$1165.007 night minimum
Nov 4, 2024 - Nov 11, 2024 $8158$1165.007 night minimum
Nov 12, 2024 - Nov 21, 2024 $8158$1165.007 night minimum
Nov 22, 2024 - Nov 30, 2024 $8158$1165.007 night minimum
Dec 1, 2024 - Dec 18, 2024 $9875$1410.007 night minimum
Dec 19, 2024 - Dec 27, 2024 $10448$1492.007 night minimum
Dec 28, 2024 - Jan 3, 2025 $10448$1492.007 night minimum
Jan 4, 2025 - Jan 10, 2025 $9875$1410.007 night minimum
Jan 11, 2025 - Jan 17, 2025 $9875$1410.007 night minimum
Jan 18, 2025 - Jan 31, 2025 $9875$1410.007 night minimum
Feb 1, 2025 - Feb 14, 2025 $9875$1410.007 night minimum
Feb 15, 2025 - Feb 21, 2025 $9875$1410.007 night minimum
Feb 22, 2025 - Apr 11, 2025 $9875$1410.007 night minimum
Apr 12, 2025 - May 28, 2025 $8158$1165.007 night minimum
May 29, 2025 - Jun 8, 2025 $8158$1165.007 night minimum
Jun 9, 2025 - Aug 10, 2025 $8158$1165.007 night minimum
Aug 11, 2025 - Oct 1, 2025 $8158$1165.007 night minimum
Oct 2, 2025 - Oct 16, 2025 $8158$1165.007 night minimum
Oct 17, 2025 - Oct 25, 2025 $8158$1165.007 night minimum
Oct 26, 2025 - Nov 2, 2025 $10740$1534.007 night minimum
Nov 3, 2025 - Nov 10, 2025 $8158$1165.007 night minimum
Nov 11, 2025 - Nov 20, 2025 $8158$1165.007 night minimum
Nov 21, 2025 - Nov 29, 2025 $8158$1165.007 night minimum
Nov 30, 2025 - Dec 19, 2025 $9875$1410.007 night minimum
Dec 20, 2025 - Dec 27, 2025 $10448$1492.007 night minimum
Dec 28, 2025 - Jan 5, 2026 $10448$1492.007 night minimum

Additional Notes:

  • High Season generally requires a 7 night minimum stay. Shorter stays of 3 - 5 nights may be available within 60 days of your arrival date or in special situations. Certain dates may not be available if they minimize optimal booking for the property's reservation calendar. Please contact us to inquire about stays less than 7 nights.
  • Shoulder and Low Season is a 3 - 5 night minimum available on reservations made within 60 days of arrival May through mid-August. From mid-August through mid-December, 3 - 5 night minimum stays are available any time.
  • Short Stays are available if there are open nights that are less than the minimum stay, shorter stays may be possible depending on the property. Please contact us to inquire.
  • Holiday, Festival, and Event Rates are 20% to 25% higher. These include, but are not limited to: Fantasy Fest, Thanksgiving, Christmas, New Years, Power Boat Races, Mini-Lobster Season, Labor Day, Parrot Heads Meeting of the Mind, 4th of July, Easter. A 7 night minimum stay is required for most major holidays, festivals, and events.

Rates and Terms are subject to change without notice. Above rates do not include taxes and fees. Click here for more details on additional fees. Please contact us for specific pricing and to confirm rates. Rates in US Funds. (305) 294-7358 Ext 1 -

Apply here for Travel Guard Trip Cancellation and Interruption Insurance.

VHKW offers promotional specials for purchasing trip insurance for stays between Aug 10 and Oct 20. Please call for more details.

  • 2nd Floor - 1 King size bed; 2 Full size beds;
  • 3rd Floor - 1 Full (double) size bed
Dec 15, 2021,
Best house I ever rented, stocked well, felt very homey

Oct 20, 2021,
Owner and Staff were professional and very helpful. We had a wonderful time at Ocean View Luxury Villa. I do have one suggestion…perhaps update the number of occupants to 4 adults and 2 children. I DO NOT recommend either adults or children using the third floor loft room. My husband and I used for the week. It is extremely dangerous and lacks the comfort of a normal room. The entire set up of the room/stairs is an accident waiting to happen. I definitely would not have rented that home for 6 adults if there was further detail included or photos of the actual loft. For your awareness, I do plan on mentioning on Trip Advisor.

Jan 31, 2021,
Loved the house! The owner thought of every detail including the most comfortable beds! The location is great for walking. The sunsets from the rooftop are better than Mallory square.

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