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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

Kat Cay

Big Torch– Canal Front | 60 Dock
3 Bedrooms | 2 Bathrooms | Sleeps 3
Monthly Rates from $4500 – $4900

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

 

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