Key West National Wildlife Refuge Rentals
From $401 per night (USD)VRBO
OFF COURSE ~ Adorable 2 BR, 2.5 Ba Townhome in Truman Annex w/ Shared Pool!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $401 per night (USD)VRBO
From $886 per night (USD)VRBO
SEAPORT SUMMIT at Galleon Resort-Beach-Pool-King Suite-BBQ-near Mallory Square
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
GALLEON RESORT LUXURY WATERFRONT PENTHOUSE with LOFT + GREAT VIEWS OF THE MARINA, OCEAN & HISTORIC SEAPORT 5th FLOOR M ...
From $886 per night (USD)VRBO
From $531 per night (USD)VRBO
**SOUL OF DUVAL @ DUVAL** Modern/Centrally Located + LAST KEY SERVICES...
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
FLEXIBLE, NO-FEE CANCELLATION INCLUDED: Rentals are 100% Refundable until 30 days prior to your arrival! There’s no do ...
From $531 per night (USD)VRBO
From $952 per night (USD)Expedia
Key West Wabi Sabi - Authentic Downtown Cottage w Pool - Steps Off Duval
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Key West Wabi Sabi is a quintessential 1930s cottage that embodies the beauty and simplicity of island-life charm. If yo ...
From $952 per night (USD)Expedia
From $1135 per night (USD)VRBO
Pavilion Villa – A Key West Private Paradise 1 Block Off Duval w Pool
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A Private Tropical Paradise ... is the feeling you get when you enter the pavilion of this award winning villa just a ha ...
From $1135 per night (USD)VRBO
From $344 per night (USD)VRBO
Freshly Renovated Cottage Old Town MONTHLY
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This freshly renovated cottage in the the heart of Old Key West is located only 2 blocks off Duval St and is a short wal ...
From $344 per night (USD)VRBO
From $914 per night (USD)VRBO
Heavenly Hideout at Rainbows End Key West - Steps from Duval w Private Pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to the end (and the beginning) of the road. There aren’t many places in the world where you can say you’re both ...
From $914 per night (USD)VRBO
From $360 per night (USD)Expedia
SOUTHARD SUNSET~2 Bedroom 1st Floor Unit in Truman Annex w/ Shared Pool!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $360 per night (USD)Expedia
From $854 per night (USD)VRBO
Amazing Penthouse
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This amazing penthouse condo has one of the best view in Key West. Located in historic Mills Place in the main part of T ...
From $854 per night (USD)VRBO
From $315 per night (USD)Expedia
KEY LIME COTTAGE ~ Renovated 3 Bedroom, 2 Bathroom Home with Private Pool!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
BAHAMA VILLAGE TREASURE... This Key West charmer is just a short stroll away from the award winning restaurants and deli ...
From $315 per night (USD)Expedia
From $695 per night (USD)VRBO
Down Island Digs - 2BR Cottage 1 Block off Duval Street Key West w/Private Pool
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Everything about this historic Key West tropical gem adds up to make a precious private garden cottage. Sitting in the m ...
From $695 per night (USD)VRBO
From $258 per night (USD)VRBO
Bahama Palms
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to “Bahama Palms” Key West! Newly renovated and full of Key West charm, this 2 bedroom 1 bath condo with washer ...
From $258 per night (USD)VRBO
From $317 per night (USD)VRBO
Sweet Sunshine Garden Flat – Downtown Key West - 2 Blocks Off Duval w Pool Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ever dream of vacationing in a sun-kissed Caribbean Cottage-style flat close to the beach, nestled behind a white picket ...
From $317 per night (USD)VRBO
From $276 per night (USD)Expedia
SALTY KISSES ~ Charming 2 Bedroom, 1.5 Bath Townhome in Truman Annex!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
PLEASE BE AWARE... We cannot accept a reservation of less than 28 nights after 12/22/25. You may book less than 28 nigh ...
From $276 per night (USD)Expedia