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Cottages &  Condo - Monthly Rentals

  
                                                                                                              

                                                                                                           

Pearls Meadows
Location: The Meadows
Pearl Street
1-866-539-7222
Off Season Rates:  
from $2500 per  Month

In Season Rates: 
 from $4000 per Month

Amenities: • Two bedrooms • Sleeps 4 • Two bathrooms • Fully equipped unit • Private Porch and Rear Courtyard • Sought after Key West Neighborhood • Good access to bars/restaurants • Close to City Marina • Pet Friendly •                     Click here for more information and photos
Sophie's Choice (Monthly rental)
Location: One and a half blocks from Duval Street
Louisa Street
1-866-539-7222

Off Season  Rates:
     from $3500

In Season  Rates: 
      from $6000

Amenities: • Three bedrooms• 3.5 bathrooms• Fully equipped • Walking distance to beach • Easy access to bars/restaurants •  Sleeps 6  • Off Street parking • Jacuzzi bathtubs • Pool Cabana • Ultimate Luxury                   Click here for more information and photos
William Street
Location: 3 blocks from Duval Street
608 William Street
1-866-539-7222

Off Season Rates:
to be advised

In Season Rates: 
from $3800

 

Amenities: • One bedroom  • One Bathrooms   • Off-Street Parking  • Large Garden • Sleeps 4  • Very central Old Town location  • Walking distance to bars and restaurants • Pets considered Click here for more information and photos
Ann's Hideaway
Location: 6 blocks from Duval Street

1000 Southard Street
Check Availability
 1-866-539-7222

Off Season  Rates:  from $2200

In Season  Rates: 
from $6000

Amenities:  • Two Bedrooms • Two Bathrooms • Loft •  Sleeps 8• Fully equipped unit • Secluded Old Town location • Easy access to Bars and Restaurants • Private Pool  • Pets considered •Click here for more information and photos
Bay Point
Location: 14 miles from Key West
Boulder Drive, Bay Point
1-866-539-7222

Off Season Rates:
from $5000

In Season Rates: 
from $6000

Front
Kitchen
View from Master Bedroom balcony
Amenities: • Oceanfront Luxury Home • Three bedrooms • Three  bathrooms • Sleeps 6 • Boat dockage • Fully equipped unit • Located on exclusive Florida Key  • Easy access to Key West •  Click here for more information and photos     
Artist's Cottage
Location: 5 blocks from Duval Street

1117 Watson Street
1-866-539-7222

Off Season Rates:
from $2000

In Season Rates: 
from $3200

Amenities: • One bedroom• plus sleeping loft • Sleeps 4 • Fully equipped unit • Old Town Location • Shared pool   Click here for more information and photos

Barefoot Breeze
Location:
1115 South Street
1-866-539-7222

Off Season Rates:  
from $4000

In Season Rates: 
from $6000

Amenities: • Two bedroom/2 bathroom • Sleeps 4 • Private Pool •  Private Jacuzzi •  Old Town location • Excellent condition • Luxurious kitchen   Click here for more information and photos
Conch Escape
Location: 6 blocks off Duval Street
1119 Watson Street
1-866-539-7222
Off Season Rates:  
from $2200

In Season Rates: 
 from $4800

 

Amenities: • Two bedrooms • Two bathrooms • Sleeps 6 • Shared pool • Off-Street parking • Pet friendly • Fully Equipped unit • Click here for more information and photos
Howe Street Hideaway
Location: 2 1/2 blocks from Duval Street

Howe Street
1-866-539-7222
 

Off Season Rates:  
from $1800

In Season Rates: 
 from $3800

 

Amenities: • Two bedrooms • Two bathrooms • Sleeps 4 • Easy access to bars/restaurants • Fully equipped unit             Click here for more information and photos
Josephine
Location: 1 mile from Duval Street

Josephine Street
1-866-539-7222

Off Season Rates:
from $2000

In Season Weekly Rates: 
from $4800

Amenities: • Two bedrooms • Two bathrooms • Sleeps 4 • Fully equipped unit • Private Pool • Close to Smather's Beach •  Lush and Tropical surroundings          Click here for more information and photos  
Key Lime Pie
Location: 5 blocks from Duval Street
Thompson Lane
1-866-539-7222
Off Season  Rates:
from $2500

In Season  Rates: 
from $4800

Amenities: • Two  bedrooms • Two Bathrooms • Sleeps 4 • Fully equipped unit • Swim-spa pool • Very close to Historic Seaport • Easy access to bars and restaurants • Off-street parking  Click here for more information and photos
Sunny Days
Location: Seven block from Duval Street
Watson Street
1-866-539-7222
 

Off Season  Rates:
from $1800

In Season  Rates: 
from $3800

 

Amenities: • Two bedrooms • Sleeps 4 •  Shared Pool • Cute Key west Compound  • Fully equipped unit •      Click here for more information and photos
 
Pearl's Promise
Location: The Meadows
818 Pearl Street
Check Availability
 1-866-539-7222
Off Season Rates:
from $4500

In Season Rates: 
from $6000

Amenities: • Two bedrooms • Two bathrooms • Sleeps 4 • Private solar heated pool • Pet friendly• Off-street Parking • Quiet residential area•  Click here for more information and photos
Perfect Pineapple
Location: 3 blocks from Duval Street
903 Southard Street
1-866-539-7222
Off Season  Rates:
from $2500

In Season  Rates: 
from $4800

Amenities: • Two  bedrooms • Two Bathrooms • Sleeps 6 • Fully equipped unit • Private pool • Pet friendly • Easy access to bars and restaurants • Close to Historic Seaport  Click here for more information and photos
Conched Out
Location: One block from Duval Street
Whitehead Street
1-866-539-7222
Off Season  Rates:
from $1800

In Season  Rates: 
from $3200

Amenities: • One  bedroom • 1 1/2 Bathrooms • Sleeps 4 • Fully equipped unit • Off-street parking •  Easy access to bars and restaurants •  Click here for more information and photos
Verandah
Location: 4 block from Duval Street
Frances Street
1-866-539-7222
Off Season  Rates:
from $2800

In Season  Rates: 
from $6000

Amenities: • Two  bedrooms • Two Bathrooms • Sleeps 4 • Fully equipped unit • Private pool •  Easy access to bars and restaurants • Pet friendly Click here for more information and photos
Off Duval Oasis
Location: Half block from Duval Street
Ennis Lane
1-866-539-7222
Off Season  Rates:
from $4500

In Season  Rates: 
from $7000

Amenities: • Three bedrooms • Three Bathrooms • Sleeps 6 • Fully equipped unit • Private pool •  Hot tub • Easy access to bars and restaurants • Pets considered  • Off-street parking Click here for more information and photos
Hidden Beauty
Location: Six blocks from Duval Street
Ashe Street
1-866-539-7222
Off Season  Rates:
from $4500

In Season  Rates: 
from $7500

Amenities: • Three bedrooms • 3.5 Bathrooms • Sleeps 6 • Fully equipped unit • Private pool •  New construction • Old Town location • Pet friendly  • Off-street parking Click here for more information and photos
Indigo Ashe
Location: Six blocks from Duval Street
Ashe Street
1-866-539-7222
Off Season  Rates:
from $4500

In Season  Rates: 
from $7500

Amenities: • Three bedrooms • 3.5 Bathrooms • Sleeps 6 • Fully equipped unit • Private pool •  New construction • Old Town location • Pet friendly  • Off-street parking Click here for more information and photos
Emma's Secret
Location: Four blocks from Duval Street
Emma Street
1-866-539-7222
Off Season  Rates:
from $2200

In Season  Rates: 
from $3800

Amenities: • Two bedrooms •Refurbished • Sleeps 4 • Fully equipped unit • Shared pool •  Good access to bars and restaurants • Click here for more information and photos

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