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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 partner websites.
BOTTOMS UP BUNGALOW - PERFECT 2 Bed/2 Bath PRIVATE POOL
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6
Villa Fleur At Shipyard Condominiums
9.8 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
Rose Lane Villas - Villa Vista - 2 Bedrooms - Downtown Key West
9.8 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4 -- Pet Friendly 
Peaceful Setting Amongst The Active Island Life Style
9.8 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
Rare Penthouse 2 Bed/2bath Additional King In Loft
9.4 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 8
Old Town 2 Bicycles, Grill, WiFi, 1st Floor, Pool! Rent 30 Days Get 20% Discount
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
MAJESTIC PARADISE @ Truman Annex - Heart Of Old Town, Key West
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 5
Henry's Penthouse On The Ocean In Key West - Weekly / Nightly Rentals
9.6 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 5
Beach Paradise In The Keys! Location! Location! 2 Blocks To Duval St
9.4 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 8
Shady Palms - Stay In Comfort- May - Aug 10% OFF - 2BD/2.5Bath - Private Pool
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 4 -- Pet Friendly
A Touch Of Bermuda In Key West
9.8 Star Rating
Key West Cottage
2 Bedroom(s) Sleeps 6 -- Pet Friendly
The Gumbo Limbo Cottage - Your Happy Place - 2BD/2.5 Bath
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 4
Caroline On My Mind - Paradise, Upgraded - 2BD/2Bath - Prime Location!
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
The Caribbean Suite - 2-K-bedroom /1 Bath/ Kitchenette/sleeps 6
9.8 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
Duval Square Retreat W/ Private Hot Tub, Pool, Parking & Walkable Location!
9.4 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6
Key West Dream Townhouse -Sleeps 6 Like New! Old Town - Perfect Location
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6
Hyatt Windward Pointe 2 Bedroom
10.0 Star Rating
Key West Apartment
2 Bedroom(s) Sleeps 6
Quiet Lane In The Heart Of Old Town, Sleeps 4, Dog Friendly
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6 -- Pet Friendly
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
**JASMINE JEWEL @ THE ANNEX** Lush Private Home & Pool + LAST KEY SERVICES…
9.8 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6
Key West, Gated Truman Annex Condo, New Waterfront Park, And Ft. Zach Beach.
9.6 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
A Touch Of Cuba In Key West
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4 -- Pet Friendly
Heart Of Key West - 2BR Waterfront At The Galleon Resort
Key West Condo
2 Bedroom(s) Sleeps 6
Old Town Beauty Built In 1883
9.4 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 7 -- Pet Friendly
Heart Of Key West - 2BR Waterfront At The Galleon Resort
Key West Condo
2 Bedroom(s) Sleeps 6
Key West Tropical Townhome On Golf Course
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 4
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
9.4 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 6
Waterfront Property - Marina Access - Spacious - Excellent Key West Condo
9.2 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 6
ISLAND DAZE ~ Adorable 2 Bedroom, 2 Bathroom Cottage 1/2 Block To Duval!
9.8 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 6 -- Pet Friendly
Location, Location, Location!!! Downtown Key West - Truman Annex!!!
9.4 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
Henry's Piece Of Paradise On The Ocean In Key West - Weekly / Nightly
9.6 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 5
Summer Is Here! Don't Wait- Book Your Dream Stay Now.
9.4 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 6
Paradise Found At The Key West Golf Club!
10.0 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 4 -- Pet Friendly
Tranquil 2-BR Condo In Truman Annex, Steps To Pool & 5-Min Walk To Duval St.
9.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 4
Sunny & Beautiful 1st Flr, Large In/Outdoors, 2BR K/T, 1 Bath, Truman Anx, Pool
10.0 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 5
Peaceful 2 BR Condo With All Amenities
9.4 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 6 -- Pet Friendly
Historic Old Town Key West - Turtle House, Sleeps 6
9.6 Star Rating
Key West Vacation Home
2 Bedroom(s) Sleeps 5
Stunning Views At The Galleon Resort In Beautiful Key West! Charming 2 Bed!
Key West Condo
2 Bedroom(s) Sleeps 6
Affordable Key West Beach Front Condo
9.6 Star Rating
Key West Condo
2 Bedroom(s) Sleeps 6