Short-Term Rentals in Sunset Key, FL: Compare 10+ Sites & Save

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  4.  Florida
  5.  Key West
  6.  Sunset Key

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2250 Best Short-Term Rentals in Sunset Key (Starting from $159)

Luxury 4BDR/4BA Penthouse
Luxury 4BDR/4BA Penthouse
House
Key West, FL, USA
0.8k from Sunset Key center

Laundry, Security/Safety, Child Friendly

4 Bedrooms8 Guests
New to Booking
$977
Average price / night
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~The Escape ~ Your own tropical escape on private island!
~The Escape ~ Your own tropical escape on private island!
House
Key West, FL, 33040, United States
0.0k from Sunset Key center

AC, Balcony, Barbecue, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$500
Average price / night
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Harbor Luxe Celebration Suites
Harbor Luxe Celebration Suites
Apartment
Key West, FL, USA
0.8k from Sunset Key center

Apartments, Accommodations, Pet-friendly, Lodgings, Places to stay

1 Bedroom20 Guests
New to Booking
$3894
Average price / night
Check Availability
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!
70 Sunset Key: Experience Idyllic Island Life, Shared Pool, Beach Access & Latitudes Restaurant!
House
Key West, FL, 33040, United States
0.0k from Sunset Key center

AC, Balcony, Dryer, Extra Bed, Free Parking, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$315
Average price / night
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Great Old Town Location, Steps from Mallory Square
Great Old Town Location, Steps from Mallory Square
Apartment
Sunset Key, Key West, Florida, USA
0.8k from Sunset Key center

Air Conditioner, Internet

1 Bedroom2 Guests
New to Booking
$159
Average price / night
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Key West Sunset Serenade - w Pool & Beach Access
Key West Sunset Serenade - w Pool & Beach Access
House
Key West, FL, 33040, United States
0.0k from Sunset Key center

AC, Balcony, Dryer, Internet, Kitchen, Laundry, Living Area, Microwave, No Smoking

2 Bedrooms6 Guests
New to Booking
$494
Average price / night
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Harborside Harmony by Last Key Realty
Harborside Harmony by Last Key Realty
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$959
Average price / night
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Villa Porta del Sole - 3BR Sunset Key Villa with Private Pool, Direct Beach Access and Sunset Ocean View!
Villa Porta del Sole - 3BR Sunset Key Villa with Private Pool, Direct Beach Access and Sunset Ocean View!
House
Key West, FL, 33040, United States
0.1k from Sunset Key center

AC, Barbecue, Dryer, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$1102
Average price / night
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Old Town Oasis by Last Key Realty
Old Town Oasis by Last Key Realty
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Parking, Lodgings, Places to stay

2 Bedrooms6 Guests
8.0

Good

1 reviews

$497
Average price / night
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Chicken Run at Custom House Inn | Unbeatable Location!
Chicken Run at Custom House Inn | Unbeatable Location!
Apartment
Key West, FL, 33040, United States
0.7k from Sunset Key center

AC, Balcony, Dryer, Free Parking, Internet, Living Area, Microwave, No Smoking, TV

1 Bedroom4 Guests
9.8

Exceptional

10 reviews

$550
Average price / night
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Underwater Cabana at Custom House Inn
Underwater Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$481
Average price / night
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Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays
Sundown Refuge | Top Location w/ Outdoor Dining & Shared Pool | Month Long Stays
Condo
Key West, FL, 33040, United States
0.7k from Sunset Key center

AC, Balcony, Barbecue, Dryer, Extra Bed, Internet, Kitchen, Laundry, No Smoking

2 Bedrooms5 Guests
9.4

Superb

31 reviews

$596
Average price / night
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Chicken Run at Custom House Inn
Chicken Run at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Cheap, Accommodations, Lodgings, Places to stay, Family

1 Bedroom4 Guests
9.0

Fabulous

2 reviews

$514
Average price / night
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Birds of a Feather at Custom House Inn | Perfect Stay on Duval Street!
Birds of a Feather at Custom House Inn | Perfect Stay on Duval Street!
Apartment
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Internet, Microwave, No Smoking, TV

1 Bedroom4 Guests
10.0

Exceptional

9 reviews

$550
Average price / night
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Citrus Queen at Custom House Inn
Citrus Queen at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$544
Average price / night
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Feather Queen at Custom House Inn | Two Vibrant Suites!
Feather Queen at Custom House Inn | Two Vibrant Suites!
Apartment
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Dryer, Free Parking, Internet, Living Area, Microwave, No Smoking, Pool, TV

2 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$1074
Average price / night
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Birds of a Feather at Custom House Inn
Birds of a Feather at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Lodgings, Places to stay

1 Bedroom4 Guests
New to Booking
$549
Average price / night
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Chicken Water Cabana at Custom House Inn
Chicken Water Cabana at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$837
Average price / night
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2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
2-bedroom condo in the heart of Key West- private beach & pool, tiki bar on-site
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Barbecue, Dryer, Fitness Equipment, Free Parking, Hot Tub, Internet, Laundry, Living Area

2 Bedrooms6 Guests
New to Booking
$652
Average price / night
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Feather Queen at Custom House Inn
Feather Queen at Custom House Inn
Apartment
Key West, FL, USA
0.9k from Sunset Key center

Apartments, Accommodations, Lodgings, Places to stay

2 Bedrooms8 Guests
New to Booking
$867
Average price / night
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Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
Hyatt Sunset Harbor, overlooking the Gulf of Mexico; 2 bd villa!
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Balcony, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave

2 Bedrooms6 Guests
9.2

Superb

5 reviews

$871
Average price / night
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Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Luxury Waterfront Stay @ The Galleon, Mins from Downtown
Apartment
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Dryer, Extra Bed, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
New to Booking
$675
Average price / night
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Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026
Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 20-27, 2026
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Arcade, Barbecue, Dryer, Elevator, Extra Bed, Fitness Equipment, Free Parking, Heater

3 Bedrooms6 Guests
New to Booking
$881
Average price / night
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Harbor House Penthouse- A
Harbor House Penthouse- A
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Balcony, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

4 Bedrooms12 Guests
10.0

Exceptional

23 reviews

$1914
Average price / night
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Harbor House Penthouse- B
Harbor House Penthouse- B
House
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking, TV

4 Bedrooms8 Guests
9.6

Exceptional

15 reviews

$1691
Average price / night
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DOWNTOWN KEY WEST 2BED OCEANFRONT!
DOWNTOWN KEY WEST 2BED OCEANFRONT!
Condo
Key West, FL, 33040, United States
0.8k from Sunset Key center

AC, Balcony, Dryer, Internet, Laundry, No Smoking, Pool, Washer

2 Bedrooms6 Guests
8.0

Good

2 reviews

$534
Average price / night
Check Availability
**HARBORSIDE HARMONY @ TRUMAN ANNEX** Waterfront Condo + LAST KEY SERVICES…
**HARBORSIDE HARMONY @ TRUMAN ANNEX** Waterfront Condo + LAST KEY SERVICES…
Condo
Key West, FL, 33040, United States
0.9k from Sunset Key center

AC, Balcony, Dryer, Elevator, Free Parking, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
9.2

Superb

5 reviews

$399
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Sunset Key.

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Sunset Key Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 2250 verified short-term rentals in Sunset Key, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Sunset Key vary depending on location, property size, and travel dates. Rates typically start from around $159 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Sunset Key include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Sunset Key, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Sunset Key often include amenities such as Wellness Facilities, Laundry, and Internet, providing a comfortable and convenient stay.

Short-term rentals in Sunset Key are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.