Key West Luxury Rentals

Welcome to Elegance in Key West: Choose Your Luxury Rental and Book Today!

Experience the pinnacle of opulence with Key West luxury rentals that feature unmatched amenities such as private pools, hot tubs, captivating views, and gourmet kitchens. Every stay with us grants you access to a complimentary concierge, ensuring your Key West vacation is a seamless blend of comfort and indulgence.

Group travels become unforgettable with our Key West Compound Rentals, offering two or more adjoining properties. If you're journeying with a furry companion, our pet-friendly Key West luxury house rentals are a perfect match.


Properties Available 153 properties available
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, complet
Hot HOT 33
The Pirate's Penthouse
Condo
$358.00 - $1,752.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (45)
SOUTHERNMOST VISTAS has everything you’re looking for to spend an unforgettable month in Key West. This recently built multi-story home plus rooftop sun deck exudes a wonderful blend of modern and island vibes. Featuring an open living plan, a lovely heated pool, and a spacious rooftop sundeck with incredible views of the Atlantic Ocean and histori
Southernmost Vistas
Private Home Pet Friendly
$300.00 - $1,150.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 (2)
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
Suite Sanctuary
Condo
$321.00 - $1,571.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (21)
Life in the Florida Keys is all about spending time outdoors, indulging in the things you love with the ones you love; and BLUE HORIZON is the perfect vacation home to experience Keys living for yourself. Whether your ideal day is floating around the large pool with a cold drink in hand, cruising the waters of the Lower Keys in your boat, or gather
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Blue Horizon
Private Home Pet Friendly
$297.00 - $1,045.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (1)
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
Casa Amarilla
Private Home Pet Friendly
$470.00 - $3,075.00 / per night
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (114)
A highlight of any Key West vacation is exploring the island and discovering for yourself Old Town's most treasured restaurants and attractions. The newest discovery awaiting you is a precious ‘gem’ of a home tucked away in a quiet enclave within Truman Annex, Key West’s most exclusive gated community. SALTWATER SAPPHIRE is a newly renovated two-st
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Saltwater Sapphire
Private Home
$475.00 - $1,709.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 2 half-baths
Guests 6 guests
Rating 5 (62)
According to the classic song, the best remedy for a belly ache is to "put de lime in de coconut and drink 'em bot' up." Last Key Realty now has the best remedy for finding comfortable accommodations for a large group vacationing in Key West: Reserve THE LIME & THE COCONUT and let us handle de rest! THE LIME & THE COCONUT is a compound of t
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The Lime & The Coconut
Compound Pet Friendly
$1,000.00 - $5,080.00 / per night
Bedrooms 6 bedrooms
Bathrooms 6 baths
Half-Bathroom 2 half-baths
Guests 16 guests
Rating 5 (81)
Finally, a large vacation home where every member of the family will be happy. From the vaulted living room with three couches and a giant 60-inch TV, to the kitchen large enough for a whole team of chefs to prepare dinner, CASA OLIVIANA has it all.THE LIVING AREA...The aforementioned living room is truly big enough for the whole family. The only d
Casa Oliviana
Private Home Pet Friendly
$395.00 - $1,274.00 / per night
Bedrooms 6 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating 5 (33)
What could be better than spending your tropical vacation in a newly built waterfront home that offers spectacular views and easy access to the beautiful waters of the Florida Keys. POSTCARD POINT is an elevated 2 bedroom home that allows you to enjoy the luxury of brand-new construction in the waterfront location you've been searching for. Picture
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Postcard Point
Private Home
$247.00 - $967.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 (48)
THE BEAMING BARRACUDA is a freshly renovated townhome located within Truman Annex, Key West's most exclusive gated community. You’ll be within walking distance to all that Key West has to offer: restaurants, shopping, attractions, and nightlife. In addition to its excellent location, THE BEAMING BARRACUDA provides an open living area and outdoor co
The Beaming Barracuda
Townhome
$333.00 - $1,299.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 1 half-baths
Guests 6 guests
Rating 5 (42)
There’s no better way to escape the hustle and bustle of reality than by sneaking off to Key West for a taste of the island life. ELEGANT ESCAPE offers first-class accommodations in a beautiful tropical setting. From the open layout and soaring ceilings of the main house to the enticing private pool and unique guest cottage, ELEGANT ESCAPE has ever
Elegant Escape
Private Home
$850.00 - $3,402.00 / per night
Bedrooms 4 bedrooms
Bathrooms 3 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating 5 (13)
Looking to make a big ‘splash’ for your next tropical vacation? MERMAID MAGIC is your answer! This newly built elevated 2 bedroom home offers incredible views and easy access to the beautiful waters of the Florida Keys. In addition, you’ll have access to the wonderful on-site amenities offered at Venture Out Resort: a heated 80-foot pool with large
Mermaid Magic
Private Home
$222.00 - $997.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (110)

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