Key West Vacation Rentals & House Rentals with Swimming Pool - 90 Rentals Available.
90 Vacation rentals
Filters applied: Swimming pool
Certificate of Excellence
Sunrise Suite Key West 2 Bed Rooms 2 Full Baths
Key West Condo
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
Responds fast! Avg. 2 hours 39 minutes
Certificate of Excellence
$240.00
from $240.00 / night
2 bedroom Condo Presented Key West Style
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- min stay varies
- Nearest beach 2 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 1 hour 12 minutes
$225.00
from $225.00 / night
Key's only real beach home. Dock and pool.
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$343.00
from $343.00 / night
The Key's only real beach house Dock and pool
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$394.00
from $394.00 / night
Key's only real beach home.Gated, private, dock,pool
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$536.00
from $536.00 / night
6 bedroom Duval Street Compound - Pool, Hot Tub, 2 parking spots - A++ Location
Key West Villa
- 6 bedrooms 6
- 7 bathrooms
- sleeps 16 16
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$2,004.00
from $2,004.00 / night
Private beach estate. Gated, tropical peace and quiet. Dock.
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$465.00
from $465.00 / night
Key West's only Real Beach House
Key West Guest house
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$393.00
from $393.00 / night
Private beach estate,gated,dock,and pool.
Key West House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 10 10
- 28 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$743.00
from $743.00 / night
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 0.2 mi
- Swimming pool
$900.00
from $900.00 / night
Bahama House - A++ Location with private pool/parking - walk to everything!
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$773.00
from $773.00 / night
Private beach estate.Dock and pool.
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$284.00
from $284.00 / night
Best Old Town Location in Key West. Two blocks from Duval Street.
Key West Townhouse
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Car not necessary
$258.00
from $258.00 / night
Southard Square Hideaway
Key West Condo
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$215.00
from $215.00 / night
President's Walk
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$221.00
from $221.00 / night
William's Loft
Key West Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$184.00
from $184.00 / night
Hidden Treasure
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$175.00
from $175.00 / night
Southard Getaway
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$230.00
from $230.00 / night
Artist Garden
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$315.00
from $315.00 / night
Bayview Harbor
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
Newton's Nest
Key West Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Ask about children
- Ask about pets
$159.00
from $159.00 / night
First Breath
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$279.00
from $279.00 / night
Sunshine Key West
Key West House
- 2 bedrooms 2
- 3 bathrooms
- sleeps 5 5
- min stay varies
- Swimming pool
- Child friendly
$286.00
from $286.00 / night
Lighthouse Villa
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$429.00
from $429.00 / night
Duval Breeze
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$265.00
from $265.00 / night
Key West Found
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$300.00
from $300.00 / night
Coconut Cottage
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$200.00
from $200.00 / night
Boat House
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$208.00
from $208.00 / night
A Barefoot Retreat
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$185.00
from $185.00 / night
Emma's Escape
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
$169.00
from $169.00 / night
Duval On The Square
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$243.00
from $243.00 / night
A Place In Paradise
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$280.00
from $280.00 / night
Linger Longer
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$225.00
from $225.00 / night
Conch Republic Retreat
Key West Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$210.00
from $210.00 / night
Key Lime Pie
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$211.00
from $211.00 / night
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.