Find Your Ideal Key West Vacation Home

Your Island Getaway Awaits

At Last Key Realty, we love Key West. We are your top choice for finding houses to rent in Key West. Need a small place for a romantic trip? Or a big house for your family? We have options that will suit all of your needs while perfectly capturing the spirit and joy of Key West.

Our houses are comfy and have a local style. You'll find our rentals in the best areas of Key West, from the historic streets of Old Town to the homes and condos on 1800 Atlantic.

Want to see all of our vacation rentals on the island? Check out our Key West Vacation Rentals page. Want a pet-friendly place near Duval Street? Or a beachfront house with an ocean view near the Truman Annex? We have the perfect rental for your Key West trip.


Properties Available 94 properties available
All year long you dream of a getaway to capture that feeling of Key West's ENDLESS SUMMER - carefree days spent tooling around Old Town on bicycles or wandering the island streets in flip flops with the sun warming your shoulders. No plans, nowhere to be, no deadlines - only a to-do list of making memories with your family and friends and possibly
Endless Summer
Private Home Pet Friendly
$675.00 - $4,048.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 12 guests
Rating Rating Rating Rating Rating 5 (221)
This precious 2 bedroom cottage with its coral front door will charm you from the moment you walk in the front gate. The front porch is private, for some quiet time reading a book. Inside, you'll see that PUERTA CORALINA reflects the simpler side of tropical living but with some useful updates.THE LIVING AREA...The living room of PUERTA CORALINA is
Puerta Coralina
Private Home Pet Friendly
$370.00 - $2,068.00 / per night
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (544)
For the ultimate stay in America's Paradise, what could be more perfect for your whole group than AMERICANA TROPICALE? This festive and patriotic home will promise a one-of-a-kind island experience. AMERICANA TROPICALE has 4 spacious bedrooms each complete with its own en-suite bathroom for privacy, a private saltwater pool, a fully equipped kitch
Americana Tropicale
Private Home Pet Friendly
$625.00 - $3,199.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (315)
The vacation opportunity of a lifetime awaits at GRAND KEY OASIS. This breathtaking one-of-a-kind property is the epitome of luxurious island living, featuring two separate homes connected by a covered pavilion that overlooks the exceptional backyard and resort-style private pool. The interior design of this compound will leave you marveling at the
Grand Key Oasis
Compound
$850.00 - $3,465.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 1 half-baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (10)
Coordinating the entire gang for a dream Key West wedding, reunion, or simply a vacation of a lifetime is hard enough... let Last Key Realty make the accommodations easy for you. ALL TOGETHER NOW is an entire block of private homes just steps from Duval Street, all yours to enjoy and with everything needed for a large group getaway: a total of thir
All Together Now
Compound Pet Friendly
$2,185.00 - $9,503.00 / per night
Bedrooms 13 bedrooms
Bathrooms 13 baths
Half-Bathroom 2 half-baths
Guests 32 guests
Rating Rating Rating Rating Rating 5 (9)
THE POLYNESIAN HOUSE is an extraordinarily unique and whimsical home, designed to capture the culture and experience of island life in an upscale private home. Viewing this home from the street, you'll know immediately how the name THE POLYNESIAN HOUSE came to be; The Polynesian-style curved roofs of the two rooms sitting atop this home are the fir
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)
The Polynesian House
Private Home
$500.00 - $1,350.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (3)
A home designed to impress the most discerning travelers, LAYOVER IN PARADISE is an oasis of comfort sure to meet the expectations of those accustomed to first class treatment. LAYOVER IN PARADISE is a newly constructed private home in the Casa Marina neighborhood that offers three spacious private suites, each with a large en-suite bathroom - and
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)
Layover In Paradise
Private Home Pet Friendly
$333.00 - $895.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (6)
Imagine a traditional conch home in the Solares Hill section of Old Town. MAISON TROPICALE is stunningly restored then decorated in a post-modern style with vivid colors and sophisticated decor. Every room is adorned with colorful art and has been furnished with unique show pieces. This brilliant decor is set against a backdrop of original Dade Cou
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)
Maison Tropicale
Private Home Pet Friendly
$250.00 - $825.00 / per night
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating Rating Rating Rating Rating 5 (18)
The moment you arrive at this midtown mansion, you’ll know your time in Key West is going to be special. The circular driveway and covered portico provide a grand entrance, which set the stage for what awaits you inside. At over 3,900 square feet, ISLAND OPULENCE is one of the largest private residences in Key West. This impressive ranch-style home
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)
Island Opulence
Private Home Pet Friendly
$250.00 - $733.00 / per night
Bedrooms 4 bedrooms
Bathrooms 4 baths
Half-Bathroom 1 half-baths
Guests 11 guests
Rating Rating Rating Rating Rating 5 (3)
Finding high-end accommodations for a large group vacation can be a challenge... let Last Key Realty make it easy for you with this one-of-a-kind compound. A ROYAL AFFAIR is the combination of three homes that offer everything a large group could desire in a Key West vacation home - a total of eleven bedrooms, twelve full bathrooms, three open livi
A Royal Affair
Compound Pet Friendly
$1,800.00 - $9,318.00 / per night
Bedrooms 11 bedrooms
Bathrooms 12 baths
Guests 34 guests
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
Saltwater Sapphire
Private Home
$475.00 - $1,482.00 / per night
Bedrooms 2 bedrooms
Bathrooms 2 baths
Half-Bathroom 2 half-baths
Guests 6 guests
Rating Rating Rating Rating Rating 5 (62)
While Old Town Key West has its fair share of impressive homes, few can compare to ENVY OF THE ISLAND, a freshly built two-story private home that combines the appearance and charm of a historic Keys home with all of the modern conveniences you have come to appreciate in new construction. This head-turning property boasts five bedrooms - unheard of
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)
Envy of the Island
Private Home Pet Friendly
$480.00 - $1,287.00 / per night
Bedrooms 5 bedrooms
Bathrooms 5 baths
Half-Bathroom 2 half-baths
Guests 10 guests
Rating Rating Rating Rating Rating 5 (7)

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