Key West Vacation Rentals & House Rentals with Swimming Pool - 77 Rentals Available.
77 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 4 minutes
Travelers’ Choice award
$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. 40 minutes
$10.00
from $10.00 / 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
Harbor Walk Hideaways
Key West B and B
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- 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
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
Southard Getaway
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$195.00
from $195.00 / night
Bayview Harbor
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$160.00
from $160.00 / night
Artist Garden
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$285.00
from $285.00 / night
President's Walk
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$195.00
from $195.00 / night
William's Loft
Key West Cottage
- 2 bedrooms 2
- 1 bathroom
- sleeps 3 3
- min stay varies
- Swimming pool
- Child friendly
- Pet friendly
$194.00
from $194.00 / night
Lighthouse Villa
Key West House
- 3 bedrooms 3
- 4 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$445.00
from $445.00 / night
Key West Found
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$250.00
from $250.00 / night
Newton's Nest
Key West Apartment
- 1 bedroom 1
- 1 bathroom
- sleeps 2 2
- min stay varies
- Swimming pool
- Ask about children
- Air conditioning
$167.00
from $167.00 / night
First Breath
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$289.00
from $289.00 / night
Emma's Escape
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$185.00
from $185.00 / night
Crowner's Jewel
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$200.00
from $200.00 / night
Coconut Cottage
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
Duval Breeze
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / night
A Barefoot Retreat
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
Boat House
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$215.00
from $215.00 / night
A Place In Paradise
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$225.00
from $225.00 / night
Linger Longer
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$180.00
from $180.00 / night
Conch Republic Retreat
Key West Cottage
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$238.00
from $238.00 / night
Tranquility
Key West Cottage
- 1 bedroom 1
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$175.00
from $175.00 / night
Sundown Refuge
Key West Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 5 5
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$264.00
from $264.00 / night
Flagler Station
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$278.00
from $278.00 / night
Amelia Home
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$325.00
from $325.00 / night
tropical Casita
Key West House
- 1 bedroom 1
- 2 bathrooms
- sleeps 2 2
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / night
Shrimp Party
Key West Townhouse
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$247.00
from $247.00 / night
Key Lime Pie
Key West House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$219.00
from $219.00 / night
Perfect Pineapple
Key West House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$241.00
from $241.00 / night
Rosalie's House
Key West House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$297.00
from $297.00 / night
Emma's Secret
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$186.00
from $186.00 / night
Key West Charming
Key West Apartment
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$150.00
from $150.00 / night
What is Travelers’ Choice award?
Tripadvisor gives a Travelers’ Choice award to accommodations, attractions and restaurants that consistently earn great reviews from travellers and are ranked within the top 10% of properties on Tripadvisor.