VIEW LIST OF ALL VACATION RENTALS
View All Vacation Rentals
Action Keys Realty is the Property Management Company for nearly 70 vacation rental homes. All of these vacation rentals are located between Marathon and Key West. Most are located on Summerland, Cudjoe and Big Pine Keys (mile markers 21-30). Most vacation homes are available for monthly rentals although some are available on a weekly basis.
All of these homes are on the water — some offer open-water views and others are on canals. These are all privately owned houses, are fully furnished, include all linens, offer fully-equipped kitchens and do not include utilities. Planning your vacation around an event or festival? Visit our Local Information page for a calendar of events for Key West and the Florida Keys.
5 O'Clock Somewhere
Cudjoe Key – Canal front | 40′ Dock | No Pets
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4100 – $4300
Agua Azul
Little Torch Key – Bay Front | 50′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $4500 – $4860
Aloe House
Cudjoe Key – Canal front | 25′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5800 – $6150
Pets
Bahia Azul
Ramrod – Ocean Views | 25′ Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7700 – $8300
Pool 
Oceanview
Barbados Landing
Ramrod – Canal Front | 20′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5100 – $5600
Pet Friendly
Bay Pointe
Saddle Brunch – Ocean Views | 45′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5700 – $6100
Pool Oceanview
Big Torch Retreat
Big Torch – Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4500 – $4900
Bitter End
Summerland – Canal Front | 35′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $8500 – $8900
Pet Friendly
Blackbeard's Bounty
Little Torch – Canal Front | Boat Dockage
3 Bedrooms | 2 Bathrooms | Sleeps 6
WINTER SPECIAL!! Normally $10,800 per month — NOW $8,900 per Month. HURRY! Before this wonderful Pool Home is Booked!
Monthly Rates – $9700 – $10,800
Private Pool
Blackbeard's Escape
Summerland – Canal Front | 2 Living Areas
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates – $9700 – $10,800
Private Pool
Blue Lagoon
Summerland – Canal Front | 40′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates – $9500
Pet Friendly Ocean view
Blue Marlin
Little Torch – Ocean Front | Walk Out Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from- $6500 – $6900
Pet Friendly OceanFront
Blue Tranquility
Ramrod – Oceanside | Kayaks
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from- $8000 – $8500
Pool
Bonefish Bungalow
Cudjoe – Ocean View | 24′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4300 – $4800
Pet Friendly Ocean view
Bow Channel Manor
Sugarloaf – Ocean View | 60′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $7300 – $7700
Pool Ocean view
Breeze Swept
Big Pine – Waterfront | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7500 – $8000
Pool 
Pet Friendly
Buccaneer Boathouse
Little Torch – Canal Front | 100′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4000 – $4200
Pet Friendly
Captain Kidd's Hideaway
Little Torch – Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5800 – $6100
Pet Friendly
Casa Azzurra
Summerland – Canal Front | 30′ Dock
4 Bedrooms | 5 Bathrooms | Sleeps 8
Monthly Rates from $11,500 – $13,500
Pool
Casa Caribe
Summerland – Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4200 – $4500
Casa Turquesa
Summerland – Ocean View | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $8000 – $8600
Pet Friendly Pool Ocean View
Cassiopea
Cudjoe – Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4200 – $4600
Pet Friendly – Dogs Only
Cayo Villa
Summerland– Canal Front | 80′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $11,000 – $12,400
Pool Ocean View
Coconut Cay
Little Torch– Screened Porch | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5900 – $6200
Pet Friendly
Conch Out
Big Pine– Canal Front | 110′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5600 – $5800
Pet Friendly
Conchy Joe's
Cudjoe – Canal Front | Boat Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7500 – $8000
Coral House
Ramrod– Canal Front | 40′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5900 – $6500
Pet Friendly Pool
Cove Isles
Summerland– Canal Front | 35′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5100 – $5400
Pet Friendly
The Four Seas
Ramrod– Canal Front | 20′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4800
Gardens Getaway
Cudjoe – Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6900 – $7400
Pet Friendly
Grouper Therapy
Little Torch – Canal Front | 30′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6100 – $6400
Pet Friendly
Hawkins Heaven
Cudjoe– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4900 – $5300
Pet Friendly
Helms House
Summerland– Ocean Front | Canal Front | 40′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 7
Monthly Rates from $7500 – $8000
Private Pool 
Ocean Front
INTO THE MYSTIC
Big Torch– Boat Dock | Canal Access
6 Bedrooms | 6 Bathrooms | Sleeps 12
Monthly Rates from $10,000 – $13,000
Island Time 1
Big Pine– Pet Friendly | Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $3800 – $4200
Pet Friendly
Island Time 2
Big Pine– Pet Friendly | Canal Front | 40′ Dock
3 Bedrooms | 1 Bathrooms | Sleeps 6
Monthly Rates from $4100 – $4400
Pet Friendly
Island Time (Full Property)
Big Pine– Pet Friendly | Canal Front | 40′ Dock
5 Bedrooms | 2 Bathrooms | Sleeps 10
Monthly Rates from $7900 – $8600
Pet Friendly
Keys Island Getaway
Summerland– Canal Front | Pool | 100 Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $12,500
Pet Friendly Pool
Keys Life
Summerland– Ocean View | Pool | 35′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6500 – $7000
Ocean View Pet Friendly Pool
Keys to the Tropics
Big Pine Key– Canal Front | 150′ Dock
3 Bedrooms + additional lower living space | 3 Bathrooms | Sleeps 8
Monthly Rates from $5900
Ocean Views
Lafitte Landing
Cudjoe– Canal Front | 30′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4100 – $4300
Pet Friendly
Latitude Adjustment
Little Torch– Canal Front | 25′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4900 – $5200
Pet Friendly
Manatee Bay
Big Pine– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4200 – $4500
Pet Friendly
Mango House
Big Pine– Canal Front | 40′ Dock
2 Bedrooms | 1.5 Bathrooms | Sleeps 4
Monthly Rates from $3900 – $4100
Margarita Villa
Little Torch– Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5100 – $5650
Pet Friendly
Montero House
Big Pine Key– Canal Front
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7600 – $8000
Pet Friendly Private Pool
Ocean View Oasis
Summerland– Ocean Front | Pool
3 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates from $13,000 – $15,000
Pool Ocean Views
Our Island Thing
Big Pine– Canal Front | Pool | 60′ Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $8500 – $8800
Pool
Palmetto Retreat
Big Pine Key– Canal Front
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5500 – $5800
Pool
Pirate's Cove
Cudjoe– Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $3100 – $3500
Pet Friendly
Pirate's Paradise
Little Torch– Private Pool
3 Bedrooms | 3.5 Bathrooms | Sleeps 6
Monthly Rates from $12,000 – $14,000
Pet Friendly Pool
Pirate's Point
Little Torch– Canal Front | 30′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4900 – $5200
Quiet Waters
Cudjoe– Canal Front | 50′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4500 – $4800
Reel Paradise
Summerland– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $8000 – $8500
Private Pool Pet Friendly
Sailfish Manor
Summerland– Canal Front | Pool | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $10,000 – $11,500
Pet Friendly Pool
Salty Retreat
Summerland– Canal Front | Pool | 80′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates from $11,995 – $14,995
Pool
Serenity
Little Torch– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5100 – $5900
Pet Friendly
Seventh Heaven
Cudjoe– Canal Front | Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $8000 – $8500
Heated Pool
South Pointe Shores
Sugarloaf– Canal Front | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6600 – $6900
Sunkissed
Ramrod– Canal Front | 26′ Dock
2 Bedrooms | 1.5 Bathrooms | Sleeps 5
Monthly Rates from $4300 – $4700
Pet Friendly
Sunset Tiki
Big Pine– Ocean View | 40′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5000 – $5300
Pet Friendly Ocean View
The Pointe
Summerland– Ocean View | 100′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $6500 – $6900
Pet Friendly Ocean View
The South House
Summerland– Private Pool | 40′ Dock
4 Bedrooms | 3 Bathrooms | Sleeps 10
Monthly Rates from $11,000 – $13,000
Pet Friendly Private Pool
Tropical Oasis
Summerland– Corner Canal | Boat Dockage
2 Bedrooms | 2 Bathrooms | Sleeps 5
Monthly Rates from $10,000 – $10,500
Pool
Tropical Sunset
Big Pine– Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $3100 – $3300
Villa Via
Cudjoe– Pool | Canal Front | Boat Dock
4 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates $11,800
Pool
Water's Edge
Big Pine – Canal Front | 50′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4900 – $5100
Pet Friendly