Home Vacation Condo Rentals By Owner In Key West, FL

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Exceptional(4)

$538.37

/ Nightly
Condo

**CALUSA SUITE @ SEAPORT INN ** Historic w/ Community Pool + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrWant to be in the heart of the action but have privacy and seclusion when it’s time to relax That’s what’s in store for your stay in the CALUSA SUITE at the Seaport Inn! You’ll be miles from reality, but just steps away from the Seaport Inn’s pool and everything else Old Town has to offer. Upon arrival and a walk past the pool, you’ll find your front door and private patio for this ground level suite. Open the door to find your studio suite equipped with a kitchenette. Included with your rental is Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, known for providing memorable vacations that'll keep Key West on your mind long after your departure.brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE ACCOMMODATIONS...brbrCALUSA SUITE is a first floor suite that is equipped with a kitchenette, chest of drawers, and a closet. There's also a King bed, a flat-screen TV, and a full bathroom with a walk-in shower.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fanbr** Flat Screen TVbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Exceptional(41)

$497.63

/ Nightly
Condo

The Trinidad at Sunrise Suites - Shared Pool

Key West, Florida, United States

Summary:brbrWelcome to Sunrise Suites, a peaceful community on Key West's southeast side. Just 1 mile from the beach and 10 minutes from Duval Street's attractions, this two-bedroom condo complex features uniquely designed units. Enjoy access to a shared hot tub, heated pool, walking paths, biking trails, a tennis court, and on-site laundry facilities—everything you need for a relaxing stay!brbrbrbrThe Space:brbrThe Trinidad Suite offers a spacious layout, featuring a master bedroom with a king-size bed and a private en-suite bathroom. The second bedroom includes a queen-size bed with direct access to the hallway bathroom. For additional sleeping arrangements, the plush blue sofa unfolds into a queen-size bed, comfortably accommodating up to 6 guests. Relax on the private balcony with seating for four, or unwind on the couch while enjoying cable TV.brbrbrbrThis condo is part of the upscale Sunrise Suites community, conveniently located just minutes from Key West International Airport, ensuring a seamless journey home. For those driving in, the condo includes one designated parking space for added convenience.brbrbrbrGuest Access:brbrOur contactless check-in procedure makes check-in easy. Guests will receive a personalized access code prior to arrival.brbrbrbrThe Neighborhood:brbrTrinidad Suite is located inside of the Sunrise Suites Resort Community located just minutes away from the World Famous Duval Street and its vibrant restaurants, art galleries and nightlife. Inside the community you can find a corner store, spa, walking and biking trails. It is also located just a short drive away from the nightly Sunset Celebration and entertainment at Mallory Square.brbrbrbrGetting Around:brbrOne of the best parts of staying in Key West is how close everything is on this charming 2x4-mile island! There are plenty of ways to get around. If walking isn’t your style, rent a bike from Fury or Island Bicycles and enjoy a morning ride to breakfast or a sunset ride along the water. Both providers offer convenient pick-up and drop-off services. For a more unique island experience, explore Key West by scooter or golf cart from Minty’s Rentals, where “island time” becomes your mantra.brbrbrbrIf you prefer traditional transportation, Uber, Lyft, and taxis are readily available. Pink Taxi is a reliable, affordable option, perfect for rides from the airport to your rental.brbrbrbrEach apartment includes one parking space, but spots are unmarked and available on a first-come, first-served basis, so proximity to your unit isn’t guaranteed. If additional spaces are available, feel free to park a second vehicle free of charge, depending on the lot’s vacancy.brbrbrbrOther Things to Note:brbrPrivate washer/dryerbrbrThere are shared washer and dryers available on the first floorbrbrUnit has both elevator and stair access.brbrPets are welcome!brbrOur requirements are as follows: brbr•40lb maximum per petbrbr•$25/per nightbrbr•2 pet maximumbrbrPlease let us know if you plan on bringing your pet.
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Exceptional(4)

$770.59

/ Nightly
Condo

Sunset views at the Galleon

Key West, Florida, United States

You will be back year after year! Unit features full kitchen with Master King Bedroom, Guest Bedroom with Twin Beds, and Pull out Sleeper Sofa in Living Room. 2 Bdrm, 2 Bath, Pull out sofa. Sleeps 6. Jacuzzi Tub in Master. Property features Pool, Sauna, Private Beach, Tiki Bar, Rooftop viewing deck, Grills and daily activities. Premium location for easy walks to Duval Street, Mallory Square, Key West Aquarium, Shipwreckers Museum, Mel Fisher Museum and much, much more.
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Exceptional(2)

$458.54

/ Nightly
Condo

**KOKOMO SUITE @ SEAPORT INN** Historic Charm & Community Pool + LAST KEY SERVIC

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival!brbrYou can skip Key Largo and Montego and go straight to Kokomo! The KOKOMO SUITE at the Seaport Inn that is. Just as suggested by the song's lyrics, you can get there fast since it is close to all of the action Duval Street, Old Town, and the Historic Seaport have to offer. You can also take it take it slow, which many residents and visitors of the island do. After experiencing the KOKOMO SUITE at the Seaport Inn’s Old Key West vibes coupled with Last Key Realty's Five-Star Guest Services & Complimentary Concierge, you’ll be saying, “that’s where we want to go!”brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE ACCOMMODATIONS...brbrKOKOMO SUITE is a first floor suite that is equipped with a kitchenette, a two-seat high-top dining table, chest of drawers, and an armoire for hanging clothes. There's also a King bed, a flat-screen TV, and a full bathroom with a walk-in shower.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fanbr** Flat Screen TVbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** Interim housekeeping provided upon requestbr** This property will accommodate up to 2 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations. There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Exceptional(2)

$436.36

/ Nightly
Condo

**ANTIGUA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf the allure of the Caribbean is calling you but you don’t want to pull out your passport, a month at the ANTIGUA SUITE at the Seaport Inn does just the trick! This suite is perched on the second floor of the Seaport Inn and just a short walk to all Old Town has to offer. Paired with Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, your month in the ANTIGUA SUITE at the Seaport Inn will have you ready to forget your passport and keep coming back to Key West!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrThe ANTIGUA SUITE is located on the 2nd floor of the Seaport Inn and is also known as unit 3. When you walk in, you’ll notice the charming living area, which features a queen sized sleeper sofa, flat screen TV and the kitchen area. The kitchen features everything you’ll need to prepare a meal at home. From there you head into the back bedroom which features a king bed and the en suite bathroom with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations.  There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Sleep 4

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Exceptional(3)

$436.36

/ Nightly
Condo

**BARBUDA SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES..

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrLooking for a month-long stay where you’ll have easy access to the heart of Key West coupled with genuine Old Town charm Quaint island decor, a cozy space, and a convenient location can all be found in the BARBUDA SUITE at the Seaport Inn. You're just a short walk to the most popular attractions in Old Town and have a comfortable space to duck out of the action when it’s time to relax. Of course, a month at BARBUDA SUITE at the Seaport Inn comes with Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, which makes island life a breeze!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrBARBUDA SUITE is located on the 2nd floor of the Seaport Inn and is also known as unit 4. Upon entering you’ll walk into the living area, featuring a queen sized sleeper sofa and a flat screen TV. Further into the unit you’ll see the fully equipped kitchen, including two seats at the kitchen bar to dine at. Beyond the kitchen sits the bedroom, featuring a queen sized bed and an en-suite bathroom with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations.  There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Exceptional(1)

$371.98

/ Nightly
Condo

**MATECUMBE SUITE @ SEAPORT INN** Guest Suite w/ Pool Access + LAST KEY SERVICES

Key West, Florida, United States

FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 60 days prior to your arrival!brbrIf you’d like to spend your month in a neighborhood engulfed in as much history as the Matecumbe Keys, look no further! Located on William Street in Old Town atop the Seaport Inn, MATECUMBE SUITE offers simple island comfort matched with easy access to all the action and historical landmarks. When you add on Last Key Realty’s Five-Star Guest Services and Complimentary Concierge, you'll see that living the island dream is not a thing of the past!brbrTHE SEAPORT INN...brbrWelcome to the Seaport Inn, where timeless island charm meets modern comfort in the heart of Old Town Key West. Seaport Inn was originally constructed in 1892 and features six suites, each boasting an en-suite bathroom and kitchen facilities. Situated just one block from the iconic Historic Seaport and a mere three blocks from the vibrant energy of Duval Street, you couldn't ask for a more convenient location to experience Key West. Steeped in history and architectural beauty, the Seaport Inn exudes historic Key West character and offers guests authentic Old Town accommodations.brbrTHE COMMUNITY POOL & TIKI BAR...brbrThe oversized outdoor common space of the Seaport Inn boasts ample space for relaxation and entertainment. Take a refreshing dip in the large pool, sip cocktails at the inviting tiki bar, or bask in the serenity of lush tropical landscaping.brbrTHE ACCOMMODATIONS...brbrMATECUMBE SUITE, also known as unit 5, perched at the top of the Seaport Inn, taking up the entire 3rd floor. You’ll enter into a secluded foyer on the 2nd floor and head straight up to the living area. Once upstairs you’ll see the queen sized sleeper sofa and the flat screen TV. This suite features a kitchenette, so great for anyone who likes to dine out at Key West’s world class restaurants. The bedroom features a queen bed and flat screen TV. There is a private bath just off the living area with a walk-in shower.brbrALL SEAPORT INN SUITES INCLUDE:brbr** Central Heat and A/Cbr** Ceiling Fansbr** Flat Screen TVs in Living Room & All Bedroomsbr** Basic stock of spicesbr** Starter supply of paper productsbr** Starter set of cleaning productsbr** Linens and Towels providedbr** Wireless high-speed Internet access & full cable includedbr** Full Time Concierge Servicebr** Fully Fenced and Lushly Landscaped Private Yardbr** Community Pool exclusively for Seaport Inn Guestsbr** Community Propane BBQ Grillbr** Community Outdoor showerbrbrOther notes:brbr** All monthly rentals include a mandatory interim clean. Multi-month stays require 1 interim clean per month.br** Additional interim cleanings availablebr** This property will accommodate up to 4 adultsbr** No Pets Allowedbr** Last Key Realty vacation homes are rented to family groups and responsible adult groups only. Groups who expect they may cause after hours noise will not be a good fit for this home and should be aware they may incur additional penalties when in residence for violations.  There will be a $500 charge for after-hours dispatch of our staff in response to calls resulting from verified noise complaints for violations by our guests in residence.
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Home Most popular vacation rentals in Key West

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Exceptional(1)

$2653.01

/ Nightly
Private vacation home

**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…

Key West, Florida, United States

Bed 10

Bed

Bath 9

Bath

Sleep 20

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Exceptional(1)

$2179.76

/ Nightly
Guest house

Custom House Inn | 8 BR Suite Compound on Duval!

Key West, Florida, United States

Bed 8

Bed

Bath 8

Bath

Sleep 25

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Exceptional(1)

$2193.75

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Hotel resort

Celebrate New Years Eve in Key West @ Exclusive Hyatt Windward - SLEEPS 6 !

Key West, Florida, United States

Bed 2

Bed

Bath 2

Bath

Sleep 6

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Exceptional(1)

$2377.08

/ Nightly
Private vacation home

**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed 7

Bed

Bath 7

Bath

Sleep 16

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Exceptional(1)

$2433.36

/ Nightly
Hotel

Family Fun in Key West with 4 Pools & Free Shuttle! 2 Waterfront Units!

Key West, Florida, United States

Bed 6

Bed

Bath 6

Bath

Sleep 12

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Exceptional(1)

$2489.04

/ Nightly
Private vacation home

**HOUSE OF THE ROYAL PALMS @ OLD TOWN** Estate Near Duval + LAST KEY SERVICES...

Key West, Florida, United States

Bed 4

Bed

Bath 4

Bath

Sleep 8

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Exceptional(1)

$2519.19

/ Nightly
Private vacation home

The Fairhaven House at Solaire Lunara Bay

Key West, Florida, United States

Bed 8

Bed

Bath 8

Bath

Sleep 16

Sleeps
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Exceptional(1)

$2606.88

/ Nightly
Private vacation home

**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...

Key West, Florida, United States

Bed 6

Bed

Bath 5

Bath

Sleep 12

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Exceptional(1)

$4253.21

/ Nightly
Private vacation home

**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…

Key West, Florida, United States

Bed 16

Bed

Bath 14

Bath

Sleep 32

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Exceptional(1)

$3363.07

/ Nightly
Private vacation home

**A ROYAL AFFAIR @ DUVAL** Three Home Compound + LAST KEY SERVICES…

Key West, Florida, United States

Bed 14

Bed

Bath 12

Bath

Sleep 34

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