Houses in Florida Keys & Key West, FL
Houses in Florida Keys & Key West, FL, from $125 a night. Book direct on each manager's site, no OTA fee.
Find stays in Florida Keys & Key West, FL
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Stays, best documented first
The Oasis
House · 1 bed · 1.5 bath · sleeps 8
Islamorada, FL
From $1,400 a night
- fireplace
- air conditioning
- central heating
- linens provided
Exact location
Book direct on YourKeys.Vacations
Blu-3BR Home, Pool/Kid-friendly
House · 1 bed · 1 bath · sleeps 6
Key West, FL
From $335 a night
- air conditioning
- dishes and silverware
- hair dryer
- dedicated workspace
Exact location
Book direct on CielStay
The Windrose Estate at Lunara Bay
House · 6 bed · 6.5 bath · sleeps 14
Key West, FL
From $1,289 a night
- air conditioning
- bbq grill
- baking sheet
- bathtub
Exact location
Book direct on CielStay
Retro Reef House | 2 Balconies | Ocean Pointe 5406
House · 2 bed · 2 bath · sleeps 2
Tavernier, FL
From $279 a night
- air conditioning
- bbq grill
- baking sheet
- barbeque utensils
City-level location
Book direct on Oasis Vacation Rentals
Splash House | Private Pool & Spa | Key Largo
House · 3 bed · 2 bath · sleeps 3
Key Largo, FL
From $299 a night
- air conditioning
- bbq grill
- bed linens
- blender
City-level location
Book direct on Oasis Vacation Rentals
107 Pelican Rd, Tavernier, FL 33070
House · 3 bed · 1 bath · sleeps 6
Tavernier, FL
From $500 a night
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Select Housing, LLC
Petronia House | Key West Home with/Heated Pool & BBQ
House · 3 bed · 3.5 bath · sleeps 6
Key West, FL
From $950 a night
- body soap
- conditioner
- hot water
- shampoo
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Autograph House | 6BR Retreat w/Guest House, Private Pools & BBQ
House · 6 bed · 6.5 bath · sleeps 12
Key West, FL
From $1,664 a night
- body soap
- hot water
- dryer
- essentials
Exact location
Book direct on Luxury Furnished Vacation Rentals & Property Management
Superb Location, Affordably Priced
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $377 a night
- air conditioning
- available in the apartment: free wifi
- barbecue grill
- bedsheets provided
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Southern Skies, Stylish Home in Old Town Key West
House · 3 bed · 2.5 bath
Key West, FL
From $445 a night
- air conditioning
- coffee/tea maker
- cookware, dishware, and utensils
- dishwasher
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
~SUNSET COVE~ Kayak or paddleboard right from your backyard!
House · 2 bed · 1 bath · sleeps 2
Key West, FL
From $451 a night
- air conditioning
- balcony
- barbecue grill
- bedsheets provided
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
The Salt Cay | Updated! Stunning Sunset View, Pool!
House · 2 bed · 1 bath · sleeps 2
Key West, FL
From $491 a night
- air conditioning
- bedsheets provided
- dryer
- elevator
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Tropical Utopia by RENT KEY WEST VACATIONS -Quiet/Gated/Pool/Balcony/Pet friendl
House · 2 bed · 2.5 bath · sleeps 2
Key West, FL
From $540 a night
- air conditioning
- bedsheets provided
- birdwatching nearby
- cycling nearby
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
THE CORNISH SUITE @ Inn on Fleming ~ 3rd Floor 2 Bedroom w/Shared Pool!
House · 2 bed · 1 bath · sleeps 4
Key West, FL
From $594 a night
- air conditioning
- coffee/tea maker
- free wifi
- hair dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Aqua Vista in Cudjoe Key
House · 2 bed · 1 bath · sleeps 4
Cudjoe Key
From $160 a night
Exact location
Book direct on infinitypropertymanagement.net
Heron Suite | Vibrant Retreat, Hot Tubs, Steps from Duval Street!
House · 1 bed · 2 bath · sleeps 4
Key West, FL
From $180 a night
- air conditioning
- barbecue grill
- bedsheets provided
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Calypso Corner - Little Torch Key
House · 2 bed · 2 bath · sleeps 6
Little Torch Key
From $185 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Croton Lane Retreat - Big Pine Key
House · 2 bed · 2 bath · sleeps 4
Big Pine Key
From $185 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Keys to the Sea + Cabana Club - Sea Turtle
House · 2 bed · 2 bath · sleeps 4
Key Colony Beach
From $185 a night
Exact location
Book direct on keys2thesea.com
Martini House - Little Torch Key
House · 2 bed · 2 bath · sleeps 4
Little Torch Key
From $185 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Seascape Vacation in Cudjoe Key
House · 1 bed · 1 bath · sleeps 4
Cudjoe Key
From $185 a night
Exact location
Book direct on infinitypropertymanagement.net
Seas The Day in Cudjoe Key
House · 2 bed · 1 bath · sleeps 4
Cudjoe Key
From $195 a night
Exact location
Book direct on infinitypropertymanagement.net
Keys to the Sea + Cabana Club - Seahorse
House · 2 bed · 2 bath · sleeps 4
Key Colony Beach
From $199 a night
Exact location
Book direct on keys2thesea.com
Reel Paradise in Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $215 a night
Exact location
Book direct on infinitypropertymanagement.net
Pirates Quay - Little Torch Key
House · 2 bed · 2 bath · sleeps 4
Little Torch Key
From $225 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Gecko House - Cudjoe Key
House · 2 bed · 2 bath · sleeps 4
Cudjoe Key
From $275 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Galleon Resort Efficiency in the old town
House · 2 bed · 1 bath · sleeps 2
Key West, FL
From $276 a night
- air conditioning
- available in the apartment: free wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
One bedroom in the heart of downtown w/ kitchen
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $276 a night
- air conditioning
- bedsheets provided
- dining area
- kitchen
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Paradise Found | Pet friendly, boating on Cudjoe
House · 3 bed · 2 bath · sleeps 6
Cudjoe Key, FL
From $277 a night
Exact location
Book direct on CielStay
Sunset Landing - Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $285 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Island Escape - Big Pine Key
House · 3 bed · 2 bath · sleeps 6
Big Pine Key
From $300 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Island Time - Open water view w. dock
House · 5 bed · 4 bath · sleeps 12
Marathon
From $300 a night
Exact location
Book direct on infinitypropertymanagement.net
Catch & Relax
House · 2 bed · 3 bath · sleeps 6
Marathon
From $305 a night
Exact location
Book direct on Seas the Keys
Paradise Blue - Little Torch Key
House · 3 bed · 2 bath · sleeps 6
Little Torch Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Paradise Palms - Cudjoe Key
House · 3 bed · 2 bath · sleeps 6
Summerland Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Reel Life - Cudjoe Key
House · 3 bed · 2 bath · sleeps 6
Cudjoe Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Summerland Key House - Summerland Key
House · 2 bed · 2 bath · sleeps 6
Summerland Key
From $315 a night
Exact location
Book direct on Island Home Rentals of the Florida Keys
Cozy & modern guest house in Key West with AC, WiFi
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $340 a night
- air conditioning
- dryer
- english
- no pets allowed
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Coconut Beach | Hot Tub | Lux Resort | Pool | Concierge
House · 2 bed · 2 bath · sleeps 6
Key West, FL
From $344 a night
- air conditioning
- balcony
- concierge services
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Castaway on the Canal + Cabana Beach Club Included
House · 2 bed · 2 bath · sleeps 4
Key Colony Beach
From $350 a night
Exact location
Book direct on Ocean Isles Vacation Rentals
Salty Kisses in Cudjoe Key
House · 2 bed · 2 bath · sleeps 4
Cudjoe Key
From $350 a night
Exact location
Book direct on infinitypropertymanagement.net
*NEW* Finer Things-Beach/Pool
House · 2 bed · 2 bath · sleeps 4
Key Colony Beach, FL
From $358 a night
- air conditioning
- coffee/tea maker
- cookware, dishware, and utensils
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Heart of Old Town getaway, perfect romantic retreat - near the action
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $393 a night
- air conditioning
- birdwatching nearby
- cycling nearby
- ecotours nearby
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Birds of a Feather at Custom House Inn | Perfect Spot On Duval!
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $415 a night
- air conditioning
- free wifi
- hair dryer
- in the city center
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Chicken Run at Custom House Inn | Unbeatable Location On Duval!
House · 1 bed · 1 bath · sleeps 2
Key West, FL
From $418 a night
- air conditioning
- deck/patio
- free wifi
- hair dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Ocean Breeze Oasis with great boating access VACA-23-410
House · 3 bed · 2 bath · sleeps 8
Marathon
From $449 a night
Exact location
Book direct on Ocean Isles Vacation Rentals
Caribbean Cottage - 2BR/2BA Sleeps 6, Heated Pools
House · 2 bed · 2 bath · sleeps 6
Key West
From $450 a night
Exact location
Book direct on Center Court Key West
Reef House Islamorada
House · 2 bed · 3 bath · sleeps 6
Islamorada
From $450 a night
Exact location
Book direct on Keys Life Vacations
Endless Summer Key Largo Vacation Home | 5 Bedrooms
House · 5 bed · 3 bath · sleeps 10
Key Largo
From $475 a night
Exact location
Book direct on Keys Life Vacations
McCartney's Manor - Deluxe K Suite W/Pvt. Spa!
House · 1 bed · 1 bath · sleeps 2
Key West
From $478 a night
Exact location
Book direct on Center Court Key West
ATLANTIC HIDEAWAY- Key West
House · 2 bed · 2 bath · sleeps 6
Key West, FL
From $480 a night
- air conditioning
- available in the condo: free wifi
- balcony
- barbecue grill
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Harrison's Hideaway-Sleeps up to 4, K & F Sl Sofa!
House · 1 bed · 1 bath · sleeps 4
Key West
From $498 a night
Exact location
Book direct on Center Court Key West
Seabreeze Key Largo Oceanside 4/2 Pool Boat Dock
House · 4 bed · 2 bath · sleeps 10
Key Largo
From $500 a night
Exact location
Book direct on Seabreeze Stay Vacation Rentals
Turtle Nest Islamorada 30ft dock 28 day 4bed 5bath
House · 4 bed · 5 bath · sleeps 8
Islamorada
From $550 a night
Exact location
Book direct on AOVRentals.com
Vaca Cut w/60' dock, 4br/4ba, 2 kitchens
House · 4 bed · 4 bath · sleeps 10
Marathon
From $589 a night
Exact location
Book direct on Melbourne Space Coast Vacation Rentals
Seabreeze Marathon Oceanside 4/3 Pool Boat Dock
House · 4 bed · 3 bath · sleeps 8
Key Colony Beach
From $600 a night
Exact location
Book direct on Seabreeze Stay Vacation Rentals
Stylish Oceanview Kayak Getaway w/ Pool & Hot Tub!
House · 3 bed · 3 bath · sleeps 8
Key Largo
From $600 a night
Exact location
Book direct on Luxury Fort Lauderdale Vacation Rental
~ Eagle's Landing ~
House · 3 bed · 2 bath · sleeps 6
Key West
From $600 a night
Exact location
Book direct on Trautman Short Term Rentals Champaign-Urbana
Private Pool Tropical Oasis - Centrally Located
House · 3 bed · 2 bath · sleeps 8
Duck Key, FL
From $605 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
Family House, 2 K BR's, Private Spa/Deck, 2 pools.
House · 2 bed · 2 bath · sleeps 6
Key West
From $678 a night
Exact location
Book direct on Center Court Key West
These are the cheapest; there are more. Narrow by facet above, or ask an agent through https://otaless.com/mcp.
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How prices are computed
Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.
Updated 2026-10-30 08:17 UTC. Prices and facts are whatever the manager published on their own site.