just booked a vacation in
iTrip.net®
  • Log In
  • START A FRANCHISE
  • Destinations
  • Vacation Deals
  • List Your Property
  • Blog
  • Contact us
  2. FL
  3. Lower Florida Keys
  4. Key West
  5. Monthly Rentals
  6. Key West

Properties in Monthly Rentals
(65 reviews)

Showing all properties. Taxes & fees included.
Occupancy Options
 
Property Type
Amenities
Reset
 View Favorites
$8268 month
Location: Key West
Rating: 4.5 Stars
Casa Cudjoe: Tropical Canal Front Retreat on Cudjoe Key, Dockage, Boater's Paradise & Dog-Friendly!
4 Beds
2 Baths
Sleeps 6
2,010 sq ft.
$9468 month
Location: Key West
Rating: 5 Stars
Slice of Paradise: Captivating Open Water Views, Deep Canal, Dockage, Heated Pool, and Pet-Friendly!
6 Beds
3 Baths
Sleeps 8
1,808 sq ft.
$7307 month
Location: Key West
Lake It Easy: Relax in This Beautiful 3BR Canal Front Home on Summerland Key, Dockage & Dog-Friendly
6 Beds
2 Baths
Sleeps 10
1,074 sq ft.
$5836 month
Location: Key West
Rating: 5 Stars
Wahoo Waterway: Charming 3BR Canal Front Home in Cudjoe Key with Dockage & Pet-Friendly Amenities!
4 Beds
2.5 Baths
Sleeps 8
2,376 sq ft.
$5231 month
Location: Key West
Rating: 5 Stars
Rising Sun: Unique, Round Canal Home on Big Pine Key, Offering Dock & Dog-Friendly Accommodations!
4 Beds
2 Baths
Sleeps 8
889 sq ft.
$10473 month
Location: Key West
Rating: 5 Stars
Caribbean Cabana: Your Perfect 3BR Oceanfront Retreat with Dockage, Pool and Breathtaking Views!
4 Beds
2 Baths
Sleeps 8
1,288 sq ft.
$14697 month
Location: Key West
The Blue Pearl: Spacious Open Water Retreat, Stunning Sunsets, Boat Bar, Room for Everyone & Fido!
8 Beds
3 Baths
Sleeps 12
4,600 sq ft.
$9570 month
Location: Key West
Pirate’s Paradise: Waterfront 3BR Retreat on Cudjoe Key with Heated/Chilled Pool & Boat Dockage
4 Beds
2 Baths
Sleeps 6
1,056 sq ft.
$8493 month
Location: Key West
Vahevala: Your Tranquil Mid-Town Key West Oasis, 3BR Home, Pool & Close to Beaches & Duval Street!
3 Beds
2 Baths
Sleeps 6
1,402 sq ft.
$7553 month
Location: Key West
Keys Breeze: 3BR Ramrod Retreat w/ Pool, Dockage, Atlantic & Gulf Access, Parking & Dog-Friendly
4 Beds
2 Baths
Sleeps 8
1,288 sq ft.
$5645 month
Location: Key West
Boater's Paradise | 170' Waterfront | 30' Dockage | Ramrod Key Retreat
6 Beds
2 Baths
Sleeps 8
1,280 sq ft.
$9755 month
Location: Key West
Rating: 5 Stars
Big Pine Paradise: Beautiful Updated 4BR Canal Front Home, Pool, Dockage, Easy Gulf/Atlantic Access
5 Beds
3 Baths
Sleeps 8
2,000 sq ft.
  • Previous
  • 1
  • 2
  • 3
Connect With Us
Vacation Rentals Vacation Destinations Vacation Deals Event Destinations View Favorites
About iTrip Blog Contact Us About Reviews Guarantee FAQ
Translate   Choose Language
Property Management List Your Property Owner FAQ Benefits Franchises
VRBO Airbnb HVMB
Copyright © 2008 - 2026 iTrip LLC
Privacy Policy | Your Privacy Choices