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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 partner websites.
~DREAMING ON DUVAL~ Grand 5 Bedroom, 4.5 Bath Home With Private Pool/parking
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10
Key West Beach House With Heated Pool, Tiki, And Dock.♿︎
9.6 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly 
EL CORAZON~ Renovated Home W/ Direct Access To Duval St. W/ Pool & Parking!
9.6 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10
~ MAISONS De LUXE ~ 2 Stunning Homes W/ Private Pool ON DUVAL.
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
Oasis In Old Town - Our Special Home
9.6 Star Rating
Key West Cottage
5 Bedroom(s) Sleeps 6 -- Pet Friendly
Key West Oasis - Truman Annex Estate
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 8
6 BR 6 BA Penthouse Suites On Duval Free Parking, Private Pool
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 24
BEAUTIFUL SANCTUARY PRIVATE ISLAND CONNECTED BY BRIDGE TO KEY WEST
9.8 Star Rating
Key West Vacation Home
9 Bedroom(s) Sleeps 20
STARS AND STRIPES ~ Magnificent Home Located In The Heart Of Old Town!
9.6 Star Rating
Key West Vacation Home
8 Bedroom(s) Sleeps 20
**SWEET AMERICANA @ OLD TOWN** 8BR/8BA Compound + 2 Pools + LAST KEY SERVICES…
10.0 Star Rating
Key West Vacation Home
10 Bedroom(s) Sleeps 20 -- Pet Friendly
**GOOD VIBRATIONS @ OLD TOWN** Unique Villa & Pool + LAST KEY SERVICES…
9.8 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
**SUMMER SOLSTICE @ OLD TOWN** Unique 9BR/9.5BA Compound + LAST KEY SERVICES…
9.6 Star Rating
Key West Vacation Home
11 Bedroom(s) Sleeps 22 -- Pet Friendly
Big Groups Welcome • Pool • Near Duval
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 16 -- Pet Friendly
CLASSIC KEY WEST - Grand Home In Old Town Location
9.4 Star Rating
Key West Vacation Home
7 Bedroom(s) Sleeps 14
WATSON HOUSE GRAND ESTATE On Simonton St
9.4 Star Rating
Key West Vacation Home
11 Bedroom(s) Sleeps 22
Oversized Home For The Whole Family W/private Pool & Dock
9.8 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
JEWEL BOX COTTAGES ~ Lush Compound With 2 Renovated Homes W/ Private Pools!
Key West Vacation Home
6 Bedroom(s) Sleeps 16 -- Pet Friendly
Just Another Day In Paradise! 2 Partial Waterview Villas! Beach Access, Pool!
8.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
Ideal Family Stay In Great Location! 2 Garden View Villas Key West Aquarium!
7.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 16 -- Pet Friendly
Florida Getaway! 2 Garden View Units! Shuttle To Key West, Onsite Parking!
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
Family Fun In Key West With 4 Pools & Free Shuttle! 2 Waterfront Units!
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
Historic Mansion In Old Town Key West With Private Pool - Sleeps 16!
9.8 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 16
**DUCHESS OF CATHERINE @ DUVAL** Brand New Home & Pool + LAST KEY SERVICES…
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
**QUEEN OF LOUISA @ DUVAL** Home In Old Town & Private Pool + LAST KEY SERVICES
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
Luxurious Oceanfront 5BR Property With Heated Pool & Waterfall
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
Poseidon's Paradise: Luxury Waterfront Rental In Key West, Stunning Backyard Oasis And Pri
9.6 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10
Crestwood House At Lunara Bay
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
**THE DUKE & THE DUCHESS @ DUVAL** Compound W/ Pool & Hot Tub + LAST KEY SERVICE
10.0 Star Rating
Key West Vacation Home
10 Bedroom(s) Sleeps 22 -- Pet Friendly
**SWEET HOME ANGELITA @ OLD TOWN** Renovated Home Off Duval + LAST KEY SERVICES
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 13 -- Pet Friendly
**THE IBIS & THE CRANE @ OLD TOWN** Compound Near Duval + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
8 Bedroom(s) Sleeps 16 -- Pet Friendly
**CASA VICTORIA @ OLD TOWN** Historic 5BR Home & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
**CASA OLIVIANA @ SOLARES HILL** Grand Home & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
**NOONA'S MANSION @ THE ANNEX** Grand Home & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 8
**STAR OF THE SEAPORT @ OLD TOWN** Huge Home & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
**SOUTHERNMOST HOSPITALITY VII** 7BR/7BA & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
7 Bedroom(s) Sleeps 16 -- Pet Friendly
**CONCH CASA GRANDE @ THE ANNEX** Home+ Pool Near Duval + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 8
**THE ROYAL COMPOUND @ THE ANNEX** Lush Estate & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 8 -- Pet Friendly
**SOUTHERNMOST HOSPITALITY V** 5BR/5BA & Pool + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 12 -- Pet Friendly
**AMERICANA TROPICALE @ OLD TOWN** Home & Pool By Duval + LAST KEY SERVICES...
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 10 -- Pet Friendly
**PLANTATION TROPICALE @ CASA EAST** Grand Estate & Pool + LAST KEY SERVICES…
10.0 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12
**ENDLESS SUMMER @ OLD TOWN** New Villa & Pool + LAST KEY SERVICES...
9.8 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 12 -- Pet Friendly
**ALL TOGETHER NOW @ OLD TOWN** Three Homes & Pools + LAST KEY SERVICES…
10.0 Star Rating
Key West Vacation Home
16 Bedroom(s) Sleeps 32 -- Pet Friendly
Altair House At Lunara Bay
9.8 Star Rating
Key West Vacation Home
6 Bedroom(s) Sleeps 14 -- Pet Friendly
NEW PRICING: DRIVE TO YOUR GETAWAY - BIG Pool, Steps To Beach & Free Parking
10.0 Star Rating
Key West Vacation Home
5 Bedroom(s) Sleeps 12
1 Block To Duval St | Banana's Foster Guesthouse
9.8 Star Rating
Key West Vacation Home
7 Bedroom(s) Sleeps 19 -- Pet Friendly
3 Bedroom 2 Bath Ocean Front Condo On Marina With Opt Boat Slip.
10.0 Star Rating
Key West Condo
5 Bedroom(s) Sleeps 8 -- Pet Friendly
**THE LIME & THE COCONUT @ OLD TOWN** 6BR/6BA Compound + LAST KEY SERVICES..
10.0 Star Rating
Key West Vacation Home
8 Bedroom(s) Sleeps 16 -- Pet Friendly
Commodore's Compound - One Block From Duval St
9.0 Star Rating
Key West Apartment
8 Bedroom(s) Sleeps 24 -- Pet Friendly