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.
Agua Azul
Little Torch Key – Bay Front | 50′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $4925 – $5200
Aloe House
Cudjoe Key – Canal front | 25′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6000 – $6350
Pet Friendly
Azul Daydream
Summerland Key – Canal front | 40′ Dock
5 Bedrooms | 3.5 Bathrooms | Sleeps 10
Monthly Rates from $11,500 – $13,000
Private Heated & Chilled Pool
Bahia Azul
Ramrod – Ocean Views | 25′ Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $8000 – $8400
Pool 
Oceanview
Barbados Landing
Ramrod – Canal Front | 20′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5400 – $5800
Pet Friendly
Barefoot Retreat
Big Torch– Ocean Front | Walk Out Dock
3 Bedrooms | 3 Bathrooms | Sleeps 14
Monthly Rates $25,000
Pool OceanFront 
Pet FRiendly
Bay Pointe
Saddlebunch – Ocean Views | 45′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $5900 – $6400
Pool Oceanview
BEAU SOLEIL
Summerland – Canal Front | 30′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates $9700
HEATED POOL Pet Friendly (with approval)
Big Torch Retreat
Big Torch – Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4700 – $5000
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
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 Marlin
Little Torch – Ocean Front | Walk Out Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from- $6800 – $7250
Pet Friendly OceanFront
Blue Tranquility
Ramrod – Oceanside | Kayaks
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from- $8000 – $8500
Pool
Blue Wahoo
Sugar Loaf Key– Canal Front Front | 75′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from- $11,850
Pet Friendly Private Pool
Bonefish Bungalow
Cudjoe – Ocean View | 24′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4600 – $5000
Pet Friendly Ocean view
Bow Channel Manor
Sugarloaf – Ocean View | 60′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $7400 – $7800
Pool Ocean view
Buccaneer Boathouse
Little Torch – Canal Front | 100′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4200 – $4400
Pet Friendly
Captain Kidd's Hideaway
Little Torch – Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6300 – $6600
Pet Friendly
Caribbean Oasis
Summerland– Ocean Front | Canal Front | 40′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 7
Monthly Rates from $8000 – $8500
Private Pool 
Ocean Front
Casa Azzurra
Summerland – Canal Front | 30′ Dock
4 Bedrooms | 5 Bathrooms | Sleeps 8
Monthly Rates from $13,000 – $14,000
Pool
Casa Caribe
Summerland – Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4500 – $4800
Casa Turquesa
Summerland – Ocean View | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $8400 – $8900
Pet Friendly Pool Ocean View
Cassiopea
Cudjoe – Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6200 – $6600
Pet Friendly – Dogs Only
Cayo Villa
Summerland– Canal Front | 80′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $12,000 – $13,000
Pool Ocean View
Coconut Cay
Little Torch– Screened Porch | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6400 – $6600
Pet Friendly
Conch Cottage
Key West – 2 Large Community Pool
1 Bedroom | 1 Bathroom | Sleeps 2
Monthly Rates from $3600
Conch Out
Big Pine– Canal Front | 110′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5800 – $6000
Pet Friendly
Conchy Joe's
Cudjoe – Canal Front | Boat Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7700 – $8300
Coral Cove
Saddlebunch – Canal Front | Dock
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7500 – $7900
Pet Friendly
Coral House
Ramrod– Canal Front | 40′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6100 – $6800
Pet Friendly Pool
Cove Isles
Summerland– Canal Front | 35′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $6000 – $6300
Pet Friendly
Cudjoe Cottage
Summerland– Canal Front | 44′ Boat Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates $5800 to $6000 (Weekly Rentals Allowed)
Dog Friendly
Dockside
Big Pine– Canal Front | 25′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4500 – $4800
Dog Friendly
El Paraiso
Cudjoe– Canal Front
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6500 – $6800
Endless Paradise
Cudjoe– Canal Front | 70ft Boat Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $10,500
Pool 
Pet Friendly
Endless Summer
Summerland– Canal Front | 60′ Concrete Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6500 – $6800
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 $7600 – $7800
Pet Friendly
Grouper Therapy
Little Torch – Canal Front | 30′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6400 – $6600
Pet Friendly
Hawkins Heaven
Cudjoe– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5400 – $5700
Pet Friendly
Keys Island Getaway
Summerland– Canal Front | Pool | 100 Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $13,000
Pet Friendly Pool
Keys Life
Summerland– Ocean View | Pool | 35′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 6
Monthly Rates from $6900 – $7500
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 11
Monthly Rates from $6100
Ocean Views
Lafitte Landing
Cudjoe– Canal Front | 30′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $4300 – $4500
Pet Friendly
Lazy Lagoon
Summerland– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 9
Monthly Rates from $7900 – $9500
Heated Pool
Manatee Bay
Big Pine– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4400 – $4700
Pet Friendly
Maracaibo Manor
Little Torch – Canal Front | 40′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $9200
Private Pool Pet Friendly
Margarita Manor
Summerland– Canal Front | 30′ Dock
4 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates from $7500 – $7800
Margarita Villa
Little Torch– Canal Front | 25′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $5500 – $6000
Pet Friendly
Montero House
Big Pine Key– Canal Front
3 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $7800 – $8200
Pet Friendly Private Pool
Ocean Breeze #27
Marathon– Canal Front | Upper Level Deck
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates $3900
Community Pool Pet Friendly
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 $8600 – $8900
Pool
Palmetto Retreat
Big Pine Key– Canal Front
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5800 – $6000
Pool
Paradise Palm
Big Pine Key– Canal Front | 28ft. Dockage
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $7900 – $8200
Heated Pool
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 $5100 – $5400
Quiet Waters
Cudjoe– Canal Front | 50′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $4650 – $4950
Reel Paradise
Summerland– Canal Front | 60′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $8300 – $8800
Private Pool Pet Friendly
Reel Sunshine
Summerland– Canal Front | 60′ Dock
3 Bedrooms | 2.5 Bathrooms | Sleeps 6
Monthly Rates from $8500 (Dec. – April)
Sailfish Manor
Summerland– Canal Front | Pool | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $11,500 – $13,000
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
San Remo Retreat
Summerland– Canal Front | Boat Dock | Dog Friendly
3 Bedrooms | 2.5 Bathrooms | Sleeps 7
Monthly Rates from $6500 – $6800
Pet Friendly
Sea Magic on Marlin
Sugar Loaf– Canal Front – Open Water View | Boat Dockage
5 Bedrooms | 4 Bathrooms | Sleeps 10
Monthly Rates – $12,870
Pet Friendly
Serenity
Little Torch– Canal Front | 60′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5300 – $6100
Pet Friendly
South Pointe Shores
Sugarloaf– Canal Front | 45′ Dock
3 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates from $6800 – $7100
Sugar Loaf Guest House
Sugar Loaf– Canal Front | 60′ Dock
3 Bedrooms | 3 Bathrooms | Sleeps 8
Monthly Rates from $11,850
Pet Friendly Heated Pool
Summerland by the Sea
Summerland– Canal Front | Large Boat Dock
4 Bedrooms | 2 Bathrooms | Sleeps 8
Monthly Rates from $10,500
Sunset Tiki
Big Pine– Ocean View | 40′ Dock
2 Bedrooms | 2 Bathrooms | Sleeps 4
Monthly Rates from $5200 – $5500
Pet Friendly Ocean View
The Snowy Grouper
Summerland– Canal Front | Dock
2 Bedrooms | 2 Bathrooms | Sleeps 6
Monthly Rates $7500
The Shores of Sugar Loaf
Sugar Loaf– Canal Front – Open Water Views | 100′ Concrete DockDock
4 Bedrooms | 3.5 Bathrooms | Sleeps 8
Monthly Rates – $14,850
Pet Friendly Private Heated Pool
The South House
Summerland– Private Pool | 40′ Dock
4 Bedrooms | 3 Bathrooms | Sleeps 10
Monthly Rates from $10,800 – $11,800
Pet Friendly Private Pool
Tropical Oasis
Summerland– Corner Canal | Boat Dockage
2 Bedrooms | 2 Bathrooms | Sleeps 5
Monthly Rates from $10,400 – $10,800
Pool
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 $5000 – $5300
Pet Friendly
Yellowstone by the Sea
Big Pine – Canal Front | 35′ Seawall
2 Bedrooms | 2 Bathrooms | Sleeps 5
Monthly Rates from $6800 – $7200
Pet Friendly Above Ground Pool
