185,000 +
Curated Listing
1300+
Destinations
24/7
Support
100%
Tailored for You
Home » Destinations » Key West »
2 Bedroom Rentals in Key West, FL
We offer Key West Vacation Rentals: Book your Home securely here and save!
Stay steps from the sand in a Key West rentals designed for convenience, coastal style, and those perfect Gulf sunsets — ideal for couples, families, and anyone who wants a seamless beach getaway.
Vacation Rentals by Owner in Key West, Florida.
We have partnered with a major provider for Vacation Rentals by Owner directly through Florida Vacation Rental Homes. With hundreds of short term rentals to choose from, we now have the selection and value to offer our visitors searching for Places To Stay in Key West.
To book a selected property, follow the "Search Availability" button or "View Rental" for Pricing & Rates, which will take you directly on our partner website.......All bookings are securely completed on our partners website!
10.0 Star Rating
Bottoms Up Bungalow - Perfect 2 Bed/2 Bath Private Pool
Vacation Home in Key West
2 Bedrooms -- Sleeps 6
9.8 Star Rating
Villa Fleur At Shipyard Condominiums
Condo in Key West
2 Bedrooms -- Sleeps 4
9.8 Star Rating
Rose Lane Villas - Villa Vista - 2 Bedrooms - Downtown Key West
Condo in Key West
2 Bedrooms -- Sleeps 4 -- Pet Friendly 
9.8 Star Rating
Peaceful Setting Amongst The Active Island Life Style
Condo in Key West
2 Bedrooms -- Sleeps 4
9.4 Star Rating
Rare Penthouse 2 Bed/2bath Additional King In Loft
Condo in Key West
2 Bedrooms -- Sleeps 8
10.0 Star Rating
Old Town 2 Bicycles, Grill, Wifi, 1st Floor, Pool! Rent 30 Days Get 20% Discount
Condo in Key West
2 Bedrooms -- Sleeps 4
10.0 Star Rating
Majestic Paradise @ Truman Annex - Heart Of Old Town, Key West
Condo in Key West
2 Bedrooms -- Sleeps 5
9.6 Star Rating
Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals
Condo in Key West
2 Bedrooms -- Sleeps 5
9.4 Star Rating
Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St
Vacation Home in Key West
2 Bedrooms -- Sleeps 8
10.0 Star Rating
Shady Palms | Historic Charm Private Pool & Effortless Island Style 2bd/2.5ba
Vacation Home in Key West
2 Bedrooms -- Sleeps 4 -- Pet Friendly
9.8 Star Rating
A Touch Of Bermuda In Key West
Cottage in Key West
2 Bedrooms -- Sleeps 6 -- Pet Friendly
10.0 Star Rating
The Gumbo Limbo Cottage - Your Happy Place - 2bd/2.5 Bath
Vacation Home in Key West
2 Bedrooms -- Sleeps 4
10.0 Star Rating
Caroline On My Mind - Paradise, Upgraded - 2bd/2bath - Prime Location!
Condo in Key West
2 Bedrooms -- Sleeps 4
9.8 Star Rating
The Caribbean Suite - 2-k-bedroom /1 Bath/ Kitchenette/sleeps 6
Condo in Key West
2 Bedrooms -- Sleeps 4
9.4 Star Rating
Key West Oasis On Duval Street : Private Hot Tub • 2 Balconies • Pool • Parking
Vacation Home in Key West
2 Bedrooms -- Sleeps 6
10.0 Star Rating
Key West Dream Townhouse -sleeps 6 Like New! Old Town - Perfect Location
Vacation Home in Key West
2 Bedrooms -- Sleeps 6
10.0 Star Rating
Hyatt Windward Pointe 2 Bedroom
Apartment in Key West
2 Bedrooms -- Sleeps 6
10.0 Star Rating
Quiet Lane In The Heart Of Old Town, Sleeps 4, Dog Friendly
Vacation Home in Key West
2 Bedrooms -- Sleeps 6 -- Pet Friendly
10.0 Star Rating
**soul Of Duval @ Duval** Modern Condo + Last Key White Glove Service...
Condo in Key West
2 Bedrooms -- Sleeps 4
9.8 Star Rating
Truman Annex Best Location In Town
Condo in Key West
2 Bedrooms -- Sleeps 4
9.8 Star Rating
**jasmine Jewel @ The Annex** Lush Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
2 Bedrooms -- Sleeps 6
9.6 Star Rating
Key West, Gated Truman Annex Condo, New Waterfront Park, And Ft. Zach Beach.
Condo in Key West
2 Bedrooms -- Sleeps 4
10.0 Star Rating
A Touch Of Cuba In Key West
Condo in Key West
2 Bedrooms -- Sleeps 4 -- Pet Friendly
Prime Waterfront! Steps To Duval & Sunset Pier! 2br With Pool & Tiki Bar At Galleon Resort
Condo in Key West
2 Bedrooms -- Sleeps 6
9.4 Star Rating
Old Town Beauty Built In 1883
Vacation Home in Key West
2 Bedrooms -- Sleeps 7 -- Pet Friendly
Prime Waterfront! Steps To Duval & Sunset Pier! 2br With Pool & Tiki Bar At Galleon Resort
Condo in Key West
2 Bedrooms -- Sleeps 6
10.0 Star Rating
Key West Tropical Townhome On Golf Course
Vacation Home in Key West
2 Bedrooms -- Sleeps 4
9.4 Star Rating
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
Condo in Key West
2 Bedrooms -- Sleeps 6
9.2 Star Rating
Key West Oasis! 2br Villa With Pools And Marina At Coconut Mallory Resort
Condo in Key West
2 Bedrooms -- Sleeps 6
9.8 Star Rating
Island Daze ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 Block To Duval!
Vacation Home in Key West
2 Bedrooms -- Sleeps 6 -- Pet Friendly
9.6 Star Rating
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly
Condo in Key West
2 Bedrooms -- Sleeps 5
9.4 Star Rating
Key West Oasis, Don't Wait- Book Your Dream Stay Now.
Condo in Key West
2 Bedrooms -- Sleeps 6
10.0 Star Rating
Paradise Found At The Key West Golf Club!
Vacation Home in Key West
2 Bedrooms -- Sleeps 4 -- Pet Friendly
9.0 Star Rating
tranquil 2-br Condo In Truman Annex, Steps To Pool & 5-min Walk To Duval St.
Condo in Key West
2 Bedrooms -- Sleeps 4
10.0 Star Rating
Sunny & Beautiful 1st Flr, Large In/outdoors, 2br K/t, 1 Bath, Truman Anx, Pool
Condo in Key West
2 Bedrooms -- Sleeps 5
9.4 Star Rating
Peaceful 2 Br Condo With All Amenities
Condo in Key West
2 Bedrooms -- Sleeps 6 -- Pet Friendly
9.6 Star Rating
Historic Old Town Key West - Turtle House, Sleeps 6
Vacation Home in Key West
2 Bedrooms -- Sleeps 5
Stunning Views At The Galleon Resort In Beautiful Key West! Charming 2 Bed!
Condo in Key West
2 Bedrooms -- Sleeps 6
9.6 Star Rating
Affordable Key West Beach Front Condo
Condo in Key West
2 Bedrooms -- Sleeps 6