Summerland Key Vacation Rentals & House Rentals - 83 Rentals Available
83 Vacation rentals
Paradise Palms
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Child friendly
- Air conditioning
$134.00
from $134.00 / 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
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
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
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
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
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
$447.00
from $447.00 / 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
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
Cruikshank
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$168.00
from $168.00 / 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
Your search has been expanded 13.8 miles to include more rentals
Private beach estate. Gated, tropical peace and quiet. Dock.
Key West House - 7.5 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- min stay varies
- Nearest beach 0 mi
- Swimming pool
- Child friendly
$466.00
from $466.00 / 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
Key's only real beach home.Gated, private, dock,pool
Key West House - 6.8 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
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
Tropical Blue Adventure Waterfront at Venture Out
Cudjoe Key House - 2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 3 nights min
- Beach/lakeside relaxation
- Nearest beach 30 mi
- Swimming pool
$229.00
from $229.00 / 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
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
$272.00
from $272.00 / 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
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
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
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
South Point Shores
Sugarloaf House - 7.9 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
Green Turtle Landing
Sugarloaf House - 7.5 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
Our Island Thing
Big Pine Key House - 6.5 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$200.00
from $200.00 / 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
Yellow Fin
Little Torch Key House - 4.8 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$100.00
from $100.00 / night
Palm Harbor
Cudjoe Key House - 3.7 miles away
- 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
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
$119.00
from $119.00 / night
Breezy Palms
Ramrod Key House - 2.2 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Ask about children
- Air conditioning
- Pet friendly
$140.00
from $140.00 / 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
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
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
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
Anchors Away
Little Torch Key House - 4.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$107.00
from $107.00 / night
Keys Escape
Cudjoe Key House - 3.7 miles away
- 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
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
$97.00
from $97.00 / night
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