Key West Vacation Rentals & House Rentals with Swimming Pool - 96 Rentals Available.
96 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. 3 hours 25 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 31 minutes
$180.00
from $180.00 / 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
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
$1,432.00
from $1,432.00 / night
Key's only real beach home. Dock and pool.
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- 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
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
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
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
$901.00
from $901.00 / 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
Bahama House - A++ Location with private pool/parking - walk to everything!
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$682.00
from $682.00 / night
Best Old Town Location in Key West
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
President's Walk
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$195.00
from $195.00 / 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
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
Artist Garden
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$285.00
from $285.00 / night
Southard Getaway
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$195.00
from $195.00 / 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
Key West Found
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$250.00
from $250.00 / night
Sunshine Key West
Key West House
- 2 bedrooms 2
- 3 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
$286.00
from $286.00 / night
Coral Garden
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
$156.00
from $156.00 / 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
Duval Breeze
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$240.00
from $240.00 / 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
Island Wind
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$226.00
from $226.00 / night
Emma's Escape
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
$168.00
from $168.00 / night
A Little Slice Of Paradise
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$162.00
from $162.00 / night
Coral Casita
Key West House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$211.00
from $211.00 / night
A Barefoot Retreat
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
$180.00
from $180.00 / night
Crowner's Jewel
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$200.00
from $200.00 / night
Bogey's Retreat
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
$162.00
from $162.00 / night
tropical Casita
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$224.00
from $224.00 / night
A Place In Paradise
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
$226.00
from $226.00 / night
Sundown Refuge
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
$264.00
from $264.00 / night
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.