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 $3300 – $3700
Agua Azul
Little Torch Key – Bay Front | 50′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $4000 – $4200
Aloe House
Cudjoe Key – Canal front | 25′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5000 – $5500
Pets
Angelfish Cove
Big Pine – Canal front | 70′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $4300 – $4750
Pets 
Pool
Bahia Azul
Ramrod – Ocean Views | 25′ Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7200 – $7700
Pool 
Oceanview
Barbados Landing
Ramrod – Canal Front | 20′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4400 – $4800
Pet Friendly
Bay Pointe
Saddle Brunch – Ocean Views | 45′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $4950 – $5250
Pet Friendly Pool Oceanview
Big Torch Retreat
Big Torch – Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $3900 – $4200
Blackbeard's Bounty
Little Torch – Canal Front | Boat Dockage
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates – $6500 – $7000
Blackbeard's Escape
Summerland – Canal Front | 2 Living Areas
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates – $9000 – $10,000
Private Pool
Blue Lagoon
Summerland – Canal Front | 40′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates – $8900
Pet Friendly Ocean view
Bow Channel Manor
Sugarloaf – Ocean View | 60′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6500 – $7000
Pool Ocean view
Breezy Palms
Little Torch – Canal Front | 47′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $5200 – $5500
Pet Friendly
Buccaneer Boathouse
Little Torch – Canal Front | 100′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $3600 – $3800
Pet Friendly
Captain Kidd's Hideaway
Little Torch – Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5200 – $5500
Pet Friendly
Casa Azzurra
Summerland – Canal Front | 30′ Dock
4 Bedrooms | 5 Bathrooms | Sleeps 8
Monthly Rates from $9900 – $11,550
Pet Friendly Pool
Casa Turquesa
Summerland – Ocean View | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7245 – $7675
Pet Friendly Pool Ocean View
Catch of the Day
Cudjoe– Canal Front | 20′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $3300 – $3750
Pet Friendly
Cayo Villa
Summerland– Canal Front | 80′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $8800 – $9350
Pet Friendly Pool Ocean View
Coconut Cay
Little Torch– Screened Porch | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5300 – $5500
Pet Friendly
Conch Out
Big Pine– Canal Front | 110′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4900 – $5150
Pet Friendly
Coral House
Ramrod– Canal Front | 40′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5150 – $5500
Pet Friendly Pool
Cove Isles
Summerland– Canal Front | 35′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4500 – $4800
Pet Friendly
Cruikshank
Summerland– Canal Front | 170′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $9000 – $10,000
Pet Friendly Ocean View
Gardens Getaway
Cudjoe – Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6200 – $6500
Pet Friendly
Grouper Therapy
Little Torch – Canal Front | 30′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4400 – $4750
Pet Friendly
Hawkins Heaven
Cudjoe– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $3800 – $4200
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
Hideaway Bay
Big Pine– Canal Front | 25′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $3500 – $3800
Pet Friendly
Island Chalet
Little Torch– Pet Friendly | 50′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4000 – $4300
Pet Friendly
Island Time 1
Big Pine– Pet Friendly | Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $3500 – $3750
Pet Friendly
Island Time 2
Big Pine– Pet Friendly | Canal Front | 40′ Dock
3 Bedrooms | 1 Bathrooms | Sleeps 6
Monthly Rates from $3550 – $3850
Pet Friendly
Island Time (Full Property)
Big Pine– Pet Friendly | Canal Front | 40′ Dock
5 Bedrooms | 2 Bathrooms | Sleeps 10
Monthly Rates from $6800 – $7000
Pet Friendly
Key Island Getaway
Summerland– Canal Front | Pool | 100 Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $10,500
Pet Friendly Pool
Keys Life
Summerland– Ocean View | Pool | 35′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5900 – $6200
Ocean View Pet Friendly Pool
Keys to the Tropics
Big Pine Key– Canal Front | 150′ Dock
3 Bedrooms + add’l lower living space | 3 Bathrooms | Sleeps 8
Monthly Rates from $4800 – $5200
La Brisa
Little Torch– Canal Front | 70′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5475 – $6000
Pet Friendly
Lafitte Landing
Cudjoe– Canal Front | 30′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $3375 – $3600
Pet Friendly
Latitude Adjustment
Little Torch– Canal Front | 25′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4300 – $4750
Pet Friendly
Manatee Bay
Big Pine– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $3500 – $3850
Pet Friendly
Mango House
Big Pine– Canal Front | 40′ Dock
2 Bedrooms | 1.5 Bathrooms | Sleeps 4
Monthly Rates from $3300 – $3600
Margarita Villa
Little Torch– Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4500 – $4800
Pet Friendly
Montero House
Big Pine Key– Canal Front
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7200 – $7500
Pet Friendly Private Pool
Our Island Thing
Big Pine– Canal Front | Pool | 60′ Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $6950 – $7250
Pool
Owl's Nest
Ramrod Key– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4300 – $4600
Pet Friendly
Palm Villa
Little Torch– Canal Front | 120′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $5900 – $6200
Palmetto Retreat
Big Pine Key– Canal Front
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $3800 – $4000
Pirate's Cove
Cudjoe– Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $2700 – $3000
Pet Friendly
Pirate's Paradise
Little Torch– Private Pool
3 Bedrooms | 3.5 Bathrooms | Sleeps64
Monthly Rates from $11,500 – $13,000
Pet Friendly Pool
Pirate's Point
Little Torch– Canal Front | 30′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4450 – $4700
Pelican Perch
Cudjoe– Canal Front | 40′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4500 – $4800
Pet Friendly
Quiet Waters
Cudjoe– Canal Front | 50′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $3900 – $4200
Ramrod Retreat
Ramrod– Canal Front | 28′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $3200 – $3600
Pet Friendly
Reel Paradise
Summerland– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7500 – $8000
Private Pool Pet Friendly
Sailfish Manor
Summerland– Canal Front | Pool | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $8850 – $9350
Pet Friendly Pool
Salty Retreat
Summerland– Canal Front | Pool | 80′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates from $10,200 – $13,400
Pool
Serenity
Little Torch– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4800 – $5000
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 $6000 – $6500
St. Croix
Ramrod– Canal Front | 52′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $2950 – $3200
Sunkissed
Ramrod– Canal Front | 26′ Dock
2 Bedrooms | 1.5 Bathrooms | Sleeps 5
Monthly Rates from $3800 – $4200
Pet Friendly
Sunset Tiki
Big Pine– Ocean View | 40′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Weekly Rates from $4500 – $4800
Pet Friendly Ocean View
The Pointe
Summerland– Ocean View | 100′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5900 – $6200
Pet Friendly Ocean View
Tropical Sunset
Big Pine– Canal Front | 40′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Monthly Rates from $2800 – $3000
Venture Out 434 - Weekly or Monthly Rental
Cudjoe– Pool | Canal Front | 25′ Dock
2 Bedrooms | 1 Bathrooms | Sleeps 4
Weekly Rates from $1500 – $2000
Pool
Water's Edge
Big Pine – Canal Front | 50′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4300 – $4500
Pet Friendly
Waterside Bay
Cudjoe – Ocean View | 40′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5300 – $5700
Ocean View