Summerland Key Vacation Rentals & House Rentals - 80 Rentals Available
80 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
$447.00
from $447.00 / 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
$200.00
from $200.00 / 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
Villa Cayo
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$267.00
from $267.00 / night
Caribbean House
Summerland Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$87.00
from $87.00 / 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
$100.00
from $100.00 / night
Gulf Shores
Summerland 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
Cruikshank
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$169.00
from $169.00 / 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
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
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
Oceanfront Home Rental in Ramrod Key, Florida
Ramrod Key House - 2.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Beach/lakeside relaxation
- Child friendly
- Air conditioning
$1.00
from $1.00 / 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
Private beach estate.Dock and pool.
Key West House - 6.8 miles away
- 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
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
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
$144.00
from $144.00 / night
Waterside Bay
Cudjoe Key House - 2.8 miles away
- 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
Bahia Azul
Ramrod Key House - 2.2 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$230.00
from $230.00 / 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
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
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
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
$394.00
from $394.00 / 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
Quiet Waters
Cudjoe Key House - 2.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$90.00
from $90.00 / 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
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
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
Cudjoe Cottage
Cudjoe Key House - 2.4 miles away
- 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
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
Mango House
Little Torch Key House - 4.5 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
Manatee Bay
Little Torch Key House - 5.2 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
Catch of the Day!
Cudjoe Key House - 1.9 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$110.00
from $110.00 / night
Key's only real beach home. Dock and pool.
Key West House - 7.6 miles away
- 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
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