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

Properties in Monthly Rentals
(60 reviews)

Showing all properties. Taxes & fees included.
Occupancy Options
SuMoTuWeThFrSa
123456789101112131415161718192021222324252627282930123456789101112
SuMoTuWeThFrSa
123456789101112131415161718192021222324252627282930123456789101112
 
Property Type
Amenities
Reset
 View Favorites
$6242 month
Location: Key West
Rating: 5 Stars
La Brisa: Discover Paradise, Updated Canal Front Home on Little Torch Key, Dockage & Dog-Friendly!
4 Beds
2 Baths
Sleeps 8
$8498 month
Location: Key West
Blue Bayou: Ideal Key West Location W/ Shared Pool, Steps from Beach, Duval Street & Mallory Square!
3 Beds
2 Baths
Sleeps 6
$5111 month
Location: Key West
Pelican Perch – 3BR Canal Front Home with Dockage, Pet-Friendly, Quick Access to Atlantic & Gulf!
4 Beds
2.5 Baths
Sleeps 6
$5315 month
Location: Key West
Castaway Cove: Charming 2BR Townhome in New Town, Key West with Shared Pool, Private Patio & Kayaks!
2 Beds
1.5 Baths
Sleeps 4
$12051 month
Location: Key West
Rating: 5 Stars
Breezy Palms: Exquisite Open Water Keys Paradise W/ Spectacular Views, Dockage, Pool & Dog-Friendly!
4 Beds
3 Baths
Sleeps 8
$5287 month
Location: Key West
Keys On Jamaica: 3BR Waterfront Home, Large Corner Lot on Ramrod Key, Convenient to Atlantic & Gulf!
6 Beds
2 Baths
Sleeps 8
$3763 month
Location: Key West
Rating: 4.5 Stars
Prime Time 2: Charming Canal Front Duplex, Your Gateway to South Pine Channel & Atlantic/Gulf Waters
3 Beds
1 Bath
Sleeps 6
$7930 month
Location: Key West
Rating: 5 Stars
The Salty Sailfish: Live the Keys Life, Stunning Canal Front Home, Pool, Dock & Dog-Friendly Bliss!
5 Beds
2 Baths
Sleeps 8
$16818 month
Location: Key West
Rating: 5 Stars
Poseidon's Paradise: Luxury Waterfront Rental in Key West, Stunning Backyard Oasis and Private Pool!
6 Beds
4.5 Baths
Sleeps 10
$9424 month
Location: Key West
Rating: 5 Stars
The Pinder House: Discover Key West Charm at Historic Eyebrow Home, Steps from Duval St & Seaport!
3 Beds
2.5 Baths
Sleeps 6
$3818 month
Location: Key West
Rating: 4 Stars
Prime Time: A Tropical Paradise on Big Pine Key, Canal Front Duplex, Swift Access to Atlantic & Gulf
3 Beds
2 Baths
Sleeps 6
$14890 month
Location: Key West
Rating: 5 Stars
$and D0llar$: Indulge in Luxury & Spectacular Open Water Views, Private Pool, Dock & Pet-Friendly!
7 Beds
4 Baths
Sleeps 12
  • 1
  • 2
  • 3
  • 4
  • Next
Connect With Us
Vacation Rentals Vacation Destinations Vacation Deals View Favorites
About iTrip Blog Contact Us About Reviews Guarantee FAQ Privacy Policy
Translate   Choose Language
Property Management List Your Property Owner FAQ Benefits Franchises
VRBO Airbnb Flipkey
Copyright © 2008 - 2025 iTrip LLC