Cudjoe Key 2-bedroom Vacation Rentals, House Rentals & More - 77 Rentals Available.
77 Vacation rentals
Filters applied: 2+ Bedrooms
Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests
Cudjoe Key House
- 6 bedrooms 6
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Nearest beach 10 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 5 minutes
$487.00
from $487.00 / night
Waterside Bay
Cudjoe Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 28 nights min
- Ask about children
- Air conditioning
- Ask about pets
$196.00
from $196.00 / night
Catch of the Day!
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$111.00
from $111.00 / night
Quiet Waters
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$107.00
from $107.00 / night
Make My Day
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$150.00
from $150.00 / night
Keys Escape
Cudjoe Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$187.00
from $187.00 / night
$130.00
from $130.00 / night
Cudjoe Cottage
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$114.00
from $114.00 / night
$215.00
from $215.00 / night
Pink House
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$167.00
from $167.00 / night
Lafitte Landing
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$95.00
from $95.00 / night
Paradise Bay
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
Cudjoe Ocean Shores
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$154.00
from $154.00 / night
Egret's Landing
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
5 O'Clock Somewhere
Cudjoe Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$92.00
from $92.00 / night
Palm Harbor
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$124.00
from $124.00 / night
Mermaid's Rest
Cudjoe Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$134.00
from $134.00 / night
Pirate's Cove
Cudjoe Key House
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$74.00
from $74.00 / night
Your search has been expanded 8 miles to include more rentals
Salty Retreat
Summerland Key House - 0.1 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 28 nights min
- Child friendly
$447.00
from $447.00 / night
Pirates Pointe
Little Torch Key House - 3.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$130.00
from $130.00 / night
Mango House
Little Torch Key House - 4.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$87.00
from $87.00 / night
Island Time 1 (half of duplex)
Big Pine Key House - 6.3 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$94.00
from $94.00 / night
Bahia Azul
Ramrod Key House - 2.1 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$247.00
from $247.00 / night
Casa Turquesa
Summerland Key House - 0.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$217.00
from $217.00 / night
Gone Fishing
Summerland Key House - 0.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 28 nights min
- Swimming pool
- Child friendly
- Air conditioning
$211.00
from $211.00 / night
Owl's Nest
Ramrod Key House - 2.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$137.00
from $137.00 / night
South Point Shores
Sugarloaf House - 8 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$170.00
from $170.00 / night
Tree House
Ramrod Key House - 2.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$104.00
from $104.00 / night
Hideaway Bay
Big Pine Key House - 5.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 31 nights min
- Child friendly
- Air conditioning
- Pet friendly
$109.00
from $109.00 / night
Key West's only Real Beach House
Key West Guest house - 6.9 miles away
- 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
Sugarloaf Sunset
Sugarloaf House - 7.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$167.00
from $167.00 / night
Bow Channel Manor
Sugarloaf House - 5.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$189.00
from $189.00 / night
Private beach estate. Gated, tropical peace and quiet. Dock.
Key West House - 7.5 miles away
- 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
Blue Marlin
Little Torch Key House - 3.4 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$132.00
from $132.00 / night
Breezy Palms
Ramrod Key House - 2.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$140.00
from $140.00 / night
Sunset Bay (weekly rental)
Ramrod Key House - 2.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 7 nights min
- Ask about children
- Air conditioning
- Pet friendly
$300.00
from $300.00 / night
Lost In Paradise
Big Pine Key House - 5.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$140.00
from $140.00 / night
Coral House
Ramrod Key House - 2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$154.00
from $154.00 / night
Key's only real beach home.Gated, private, dock,pool
Key West House - 6.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Child friendly
- Air conditioning
$536.00
from $536.00 / night
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