Summerland Key Vacation Rentals & House Rentals - 79 Rentals Available
79 Vacation rentals
Paradise Palms
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Child friendly
- Air conditioning
$151.00
from $151.00 / night
Gone Fishing
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 28 nights min
- Swimming pool
- Child friendly
- Air conditioning
$211.00
from $211.00 / night
Villa Cayo
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$284.00
from $284.00 / night
Cruikshank
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$187.00
from $187.00 / night
Cove Isles
Summerland Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$120.00
from $120.00 / night
Another Day In Paradise
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 28 nights min
- Child friendly
$268.00
from $268.00 / night
Caribbean Dream
Summerland Key House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$217.00
from $217.00 / night
$447.00
from $447.00 / night
Blue Lagoon
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$200.00
from $200.00 / night
Big Torch Retreat
Summerland 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
Casa Turquesa
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$217.00
from $217.00 / night
Your search has been expanded 13.8 miles to include more rentals
Bay Pointe
Sugarloaf House - 9.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$154.00
from $154.00 / night
Buccaneer Boathouse
Little Torch Key House - 3.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
$114.00
from $114.00 / night
Paradise Bay
Cudjoe Key House - 2.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
Coral House
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
$154.00
from $154.00 / night
Breezy Palms
Ramrod Key House - 2.2 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
Bonefish Lodge
Key West House - 13.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 28 nights min
- Child friendly
$150.00
from $150.00 / 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
Blue Tranquility
Ramrod Key House - 2.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Child friendly
- Pet friendly
$167.00
from $167.00 / night
Island Time 2 (half of duplex)
Big Pine Key House - 6.4 miles away
- 3 bedrooms 3
- 1 bathroom
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$100.00
from $100.00 / night
Island Chalet
Little Torch Key House - 3.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$120.00
from $120.00 / night
Bernie's Bungalow
Big Pine Key House - 4.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Child friendly
- Pet friendly
$114.00
from $114.00 / night
Blue Heron
Big Pine Key House - 4.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$93.00
from $93.00 / night
Pirate's Cove
Cudjoe Key House - 2 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$74.00
from $74.00 / night
Oceanview Estate 15 minutes from Key West - 6 bedroom accommodate 13 guests
Cudjoe Key House - 3.6 miles away
- 6 bedrooms 6
- 3 bathrooms
- sleeps 14 14
- min stay varies
- Nearest beach 10 mi
- Swimming pool
- Child friendly
$487.00
from $487.00 / night
Key West's only Real Beach House
Key West Guest house - 6.8 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
Bow Channel Manor
Sugarloaf House - 5.5 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
Lafitte Landing
Cudjoe Key House - 2.4 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$95.00
from $95.00 / night
5 O'Clock Somewhere
Cudjoe Key House - 2.2 miles away
- 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
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
Mermaid's Rest
Cudjoe Key House - 2.3 miles away
- 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
Tree House
Ramrod Key House - 2.5 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
Palm Villa
Little Torch Key House - 3.7 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$190.00
from $190.00 / night
Cudjoe Ocean Shores
Cudjoe Key House - 1.9 miles away
- 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
Pink House
Cudjoe Key House - 3.7 miles away
- 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
Private beach estate,gated,dock,and pool.
Key West House - 7 miles away
- 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
Blue Marlin
Little Torch Key House - 3.5 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
Pirates Pointe
Little Torch Key House - 3.6 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
Egret's Landing
Cudjoe Key House - 2.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
Owl's Nest
Ramrod Key House - 2.2 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
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.