185,000 +
Curated Listing
1300+
Destinations
24/7
Support
100%
Tailored for You
Home » Destinations » Key West »
5+ Bedroom Large Home 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
~dreaming On Duval~ 5 Bedroom, 4.5 Bath Home With Private Pool And Parking
Vacation Home in Key West
5 Bedrooms -- Sleeps 10
9.6 Star Rating
Key West Beach House With Heated Pool, Tiki, And Dock.♿︎
Vacation Home in Key West
5 Bedrooms -- Sleeps 10 -- Pet Friendly 
9.8 Star Rating
El Corazon~ Renovated Home W/ Direct Access To Duval St. W/ Pool & Parking!
Vacation Home in Key West
5 Bedrooms -- Sleeps 10
10.0 Star Rating
~ Maisons De Luxe ~ 2 Stunning Homes W/ Private Pool On Duval.
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
9.6 Star Rating
Oasis In Old Town - Our Special Home
Cottage in Key West
5 Bedrooms -- Sleeps 6 -- Pet Friendly
10.0 Star Rating
Key West Oasis - Truman Annex Estate
Vacation Home in Key West
5 Bedrooms -- Sleeps 8
10.0 Star Rating
6 Br 6 Ba Duval Street Suites Free Parking & Pool
Vacation Home in Key West
6 Bedrooms -- Sleeps 24
9.8 Star Rating
Thompson Island - Private Island Estate In Key West
Vacation Home in Key West
9 Bedrooms -- Sleeps 20
9.6 Star Rating
Stars And Stripes ~ Magnificent Home Located In The Heart Of Old Town!
Vacation Home in Key West
8 Bedrooms -- Sleeps 20
10.0 Star Rating
**sweet Americana** 8br/8ba Compound & 2 Pools + Last Key White Glove Service...
Vacation Home in Key West
10 Bedrooms -- Sleeps 20 -- Pet Friendly
9.8 Star Rating
**good Vibrations @ Old Town** Villa & Pool + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 10 -- Pet Friendly
9.6 Star Rating
**summer Solstice @ Old Town** 9br Compound + Last Key White Glove Service...
Vacation Home in Key West
11 Bedrooms -- Sleeps 22 -- Pet Friendly
10.0 Star Rating
Big Groups Welcome • Pool • Near Duval
Vacation Home in Key West
5 Bedrooms -- Sleeps 16 -- Pet Friendly
9.4 Star Rating
Classic Key West - Grand Home In Old Town Location
Vacation Home in Key West
7 Bedrooms -- Sleeps 14
9.6 Star Rating
Watson House Grand Estate On Simonton St
Vacation Home in Key West
11 Bedrooms -- Sleeps 22
9.8 Star Rating
Oversized Home For The Whole Family W/private Pool & Dock
Vacation Home in Key West
5 Bedrooms -- Sleeps 12 -- Pet Friendly
Jewel Box Cottages ~ Lush Compound With 2 Renovated Homes W/ Private Pools!
Vacation Home in Key West
6 Bedrooms -- Sleeps 16 -- Pet Friendly
8.0 Star Rating
Just Another Day In Paradise! 2 Partial Waterview Villas! Beach Access, Pool!
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
7.0 Star Rating
Ideal Family Stay In Great Location! 2 Garden View Villas Key West Aquarium!
Vacation Home in Key West
6 Bedrooms -- Sleeps 16 -- Pet Friendly
Florida Getaway! 2 Garden View Units! Shuttle To Key West, Onsite Parking!
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
Family Fun In Key West With 4 Pools & Free Shuttle! 2 Waterfront Units!
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
9.8 Star Rating
William Skelton Home - Sleeps 16 Just Off Duval St
Vacation Home in Key West
6 Bedrooms -- Sleeps 16
10.0 Star Rating
**duchess Of Catherine @ Duval** Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
**queen Of Louisa @ Duval** Private Pool + Last Key White Glove Service...
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
Luxurious Oceanfront 5br Property With Heated Pool & Waterfall
Vacation Home in Key West
5 Bedrooms -- Sleeps 12 -- Pet Friendly
9.6 Star Rating
Poseidon's Paradise: Luxury Waterfront Rental In Key West, Stunning Backyard Oasis And Pri
Vacation Home in Key West
5 Bedrooms -- Sleeps 10
9.4 Star Rating
Crestwood House At Lunara Bay
Vacation Home in Key West
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
**the Duke & The Duchess** Compound W/ Pool + Last Key White Glove Service...
Vacation Home in Key West
10 Bedrooms -- Sleeps 22 -- Pet Friendly
10.0 Star Rating
**sweet Home Angelita @ Old Town** Home + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 13 -- Pet Friendly
10.0 Star Rating
**the Ibis & The Crane @ Old Town** Compound + Last Key White Glove Service...
Vacation Home in Key West
8 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
**casa Victoria @ Old Town** Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
**casa Oliviana @ Solares Hill** Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
**noona's Mansion @ The Annex** Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
6 Bedrooms -- Sleeps 8
10.0 Star Rating
**star Of The Seaport @ Old Town** Pool + Last Key White Glove Service......
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
**southernmost Hospitality Vii** 7br & Pool + Last Key White Glove Service...
Vacation Home in Key West
7 Bedrooms -- Sleeps 16 -- Pet Friendly
10.0 Star Rating
**conch Casa Grande** Home+ Pool Near Duval + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 8
10.0 Star Rating
**the Royal Compound @ The Annex** Pool + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 8 -- Pet Friendly
10.0 Star Rating
**southernmost Hospitality V** 5br/5ba & Pool + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
**americana Tropicale @ Old Town** Home & Pool + Last Key White Glove Service...
Vacation Home in Key West
5 Bedrooms -- Sleeps 10 -- Pet Friendly
10.0 Star Rating
**plantation Tropicale @ Casa East** Grand Estate & Pool + Last Key Services…
Vacation Home in Key West
6 Bedrooms -- Sleeps 12
9.8 Star Rating
**endless Summer @ Old Town** New Villa & Pool + Last Key White Glove Service...
Vacation Home in Key West
6 Bedrooms -- Sleeps 12 -- Pet Friendly
10.0 Star Rating
**all Together Now @ Old Town** 3 Home Compound + Last Key White Glove Service…
Vacation Home in Key West
16 Bedrooms -- Sleeps 32 -- Pet Friendly
9.8 Star Rating
Altair House At Lunara Bay
Vacation Home in Key West
6 Bedrooms -- Sleeps 14 -- Pet Friendly
10.0 Star Rating
New Pricing: Drive To Your Getaway - Big Pool, Steps To Beach & Free Parking
Vacation Home in Key West
5 Bedrooms -- Sleeps 12
9.8 Star Rating
1 Block To Duval St | Banana's Foster Guesthouse
Vacation Home in Key West
7 Bedrooms -- Sleeps 19 -- Pet Friendly
10.0 Star Rating
3 Bedroom 2 Bath Ocean Front Condo On Marina With Opt Boat Slip.
Condo in Key West
5 Bedrooms -- Sleeps 8 -- Pet Friendly
10.0 Star Rating
**the Lime & The Coconut @ Old Town** Compound + Last Key White Glove Service...
Vacation Home in Key West
8 Bedrooms -- Sleeps 16 -- Pet Friendly
9.2 Star Rating
Commodore's Compound - One Block From Duval St
Apartment in Key West
8 Bedrooms -- Sleeps 24 -- Pet Friendly