Villa Bella

12 guests · 4 bedrooms · 4 baths

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at ARCHIPELAGO in the Truman Annex for $798 for your next trip.

8.4 / 10.0

Excellent(307 Ratings)

Rose Lane Villas

Villa

2 guests · 1 bedroom · 1 bath

Free WiFi/internet · Air conditioning · Pool

Soak up the beauty of Key West in our Villa, Rose Lane Villas. With a range of amenities such as Free Parking, Pets allowed and Garden, you'll feel right at home.

10.0 / 10.0

Outstanding(2 Ratings)

ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool

12 guests · 5 bedrooms · 3 baths

Enjoy the best of Key West in our House, ISLAND TIME - 5 Bed/3 Bath OldTown Complex - MONTHLY - Private pool. A stunning property with amenities including Family friendly, and more.

Sundown Refuge by Avantstay Top Location w/ Patio, Outdoor Dining, Shared Pool Month Long Stays

2 guests

Free WiFi/internet · Air conditioning · Pool

Cottage in Key West, for $521 per night is great for your next (business stay, family stays, couples stay, getaway vacation, etc.)

9.1 / 10.0

Outstanding(98 Ratings)

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

12 guests · 4 bedrooms · 2 baths

This attractive Cottage in Key West, $862 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

9.2 / 10.0

Outstanding(98 Ratings)

Two Rustic Cottages with Private Hot Tubs & Private Parking - Dogs OK

12 guests · 4 bedrooms · 2 baths

Experience the best of Key West with this Cottage available for $884. This property is equipped with amenities including Pets allowed, Family friendly and Non-smoking, and more.

You can save with One Key

10.0 / 10.0

Outstanding(1 Rating)

Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!

12 guests · 4 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · Pool

Soak up the beauty of Key West in our Cottage, Old Town Key West Compound with Pool, Parking and Privacy One Block Off Duval!. With a range of amenities such as Air conditioning, Dryer and WiFi/Internet, you'll feel right at home.

JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!

16 guests · 6 bedrooms · 6 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a memorable stay in Key West? Our House might just be what you're looking for. Enjoy amenities including Air conditioning, Balcony/Terrace and Dryer, and more during your stay.

10.0 / 10.0

Outstanding(4 Ratings)

Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West

12 guests · 4 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · TV

Looking to create some memories in Key West? Look no further than our House, Newly Renovated Luxury Coastal Home in the Heart of Old Town Key West. Enjoy top-rated amenities including Air conditioning, Dryer and WiFi/Internet, and more.

JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!

16 guests · 6 bedrooms · 6 baths

Free WiFi/internet · Air conditioning · Pool

Looking to create some memories in Key West? Look no further than our House, JEWEL BOX COTTAGES ~ Lush Compound with 2 Renovated Homes w/ Private Pools!. Enjoy top-rated amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

10.0 / 10.0

Outstanding(8 Ratings)

SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!

12 guests · 4 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · Pool

Business stays, family stays, couples stay, getaway vacation, and rental in Key West at SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool! for $903 for your next trip.

10.0 / 10.0

Outstanding(4 Ratings)

The Most Perfect Old Town Key West Location for a Retreat!

12 guests · 4 bedrooms · 3 baths

Free WiFi/internet · Air conditioning · Pool

Experience the best of Key West with this House available for $881. This property is equipped with amenities including Air conditioning, Balcony/Terrace and Dryer, and more.

Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays

2 guests

Free WiFi/internet · Air conditioning · Pool

Are you ready to indulge in a relaxing getaway? Our Cottage in Key West has everything you need for a rejuvenating stay. Treat yourself to Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays's exceptional amenities, such as Non-smoking, Air conditioning and Dryer.

Sundown Refuge by Avantstay Top Location w/ Patio, Outdoor Dining, Shared Pool Month Long Stays

2 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Discover the beauty of Key West with a stay at Sundown Refuge by Avantstay Top Location w/ Patio, Outdoor Dining, Shared Pool Month Long Stays, a top rated Cottage with amenities such as Non-smoking, Air conditioning and Dryer, and more.

10.0 / 10.0

Outstanding(8 Ratings)

SUNCATCHER~4 Bedroom, 4 Bathroom in Old Town with Pool!

12 guests · 4 bedrooms · 4 baths

Free WiFi/internet · Air conditioning · Pool

Looking for a House in Key West, this House for $903 per night for your business stay, family stay, couples stay, getaway vacation, on your next trip.

You can save with One Key

9.6 / 10.0

Outstanding(13 Ratings)

Banyan Court downtown condo- 2 bedroom, 2.5 bath, walkable, parking, pool

4 guests · 2 bedrooms · 2 baths

This House in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key

Villa

5 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

This attractive Villa in Key West, $535 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Casa Oliviana by Last Key Realty

12 guests · 1 bedroom · 4 baths

Free WiFi/internet · Pool · Spa

Looking for the perfect place to call home during your trip to Key West? This House offers a comfort and style with top-notch amenities, including Free Parking, Pets allowed and Tennis court, and more.

You can save with One Key

Modern Luxury Meets Island Privacy: Executive Villa on Exclusive Sunset Key

Villa

5 guests · 2 bedrooms · 2 baths

WiFi/Internet · Air conditioning · Pool

This Villa in Key West, is the right price for your (business stay, family stays, couples stay, getaway vacation, etc.) today!

Truman's Hideaway by Avantstay Great Location w/ Patio, Outdoor Dining, BBQ & Shared Pool! Week Long Stays

2 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

The best choice in Key West for Cottage, for $501 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

Hyatt Sunset Harbor Resort Timeshare available 2 weeks only Mar22-Apr5, 2026

6 guests · 2 bedrooms · 2 baths

Looking for a memorable stay in Key West? Our House might just be what you're looking for. Enjoy amenities including Family friendly, and more during your stay.

You can save with One Key

9.8 / 10.0

Outstanding(57 Ratings)

Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!

6 guests · 3 bedrooms · 3 baths

WiFi/Internet · Air conditioning · TV

Soak up the beauty of Key West in our House, Casa Cristol- Family and Pet Friendly - Classic KW Charm Superb Location!. With a range of amenities such as Air conditioning, Balcony/Terrace and Dryer, you'll feel right at home.

A Place In Paradise by Avantstay Key West Walkable w/ Shared Pool Week Long Stays Only

2 guests

Free WiFi/internet · Air conditioning · Pool

The best choice in Key West for Cottage, for $312 per night for your (business stay, family stay, couples stay, getaway vacation, etc.)

8.0 / 10.0

Excellent(1 Rating)

Sunset Harbor - Old Town Key West Location - Beautiful Property

Apartment

4 guests · 1 bedroom · 1 bath

WiFi/Internet · Air conditioning · Pool

Nestled in Key West, this Apartment is perfect for your next vacation. Enjoy Sunset Harbor - Old Town Key West Location - Beautiful Property's top-rated amenities, including Air conditioning, WiFi/Internet and Kitchen, and more.

2 Sunset Harbor Resort, Marina, In Town, Hot Tub!

Resort

6 guests · 2 bedrooms · 2 baths

Looking for a business stay, family stay, couples stay, getaway vacation, or traveling to Key West, at $1,560 per night for your next great vacation.

A Place In Paradise by Avantstay Key West Walkable w/ Shared Pool Week Long Stays Only

2 guests · 2 bedrooms · 2 baths

Free WiFi/internet · Air conditioning · Pool

Indulge in a peaceful retreat at A Place In Paradise by Avantstay Key West Walkable w/ Shared Pool Week Long Stays Only, our elegant Cottage in Key West. Enjoy amenities including Non-smoking, Air conditioning and Balcony/Terrace, and more.

8.0 / 10.0

Excellent(1 Rating)

Sunset Harbor - Old Town Key West Location - Beautiful Property

Apartment

4 guests · 1 bedroom · 1 bath

WiFi/Internet · Air conditioning · Pool

Indulge in a peaceful retreat at Sunset Harbor - Old Town Key West Location - Beautiful Property, our elegant Apartment in Key West. Enjoy amenities including Air conditioning, WiFi/Internet and Kitchen, and more.

Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.

Apartment

6 guests · 2 bedrooms · 2 baths

Enjoy the best of Key West in our Apartment, Hyatt Sunset Harbor on the Water-Luxury Key West 2 Bedroom Condo Dec 21-Dec 28.. A stunning property with amenities including Family friendly, and more.