Summerland Key Vacation Rentals & House Rentals - 54 Rentals Available
54 Vacation rentals
Cove Isles
Summerland Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Ask about pets
$160.00
from $160.00 / night
$447.00
from $447.00 / 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
$140.00
from $140.00 / night
Casa Turquesa
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$256.00
from $256.00 / night
Cruikshank
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$334.00
from $334.00 / night
Blue Lagoon
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$230.00
from $230.00 / night
Villa Cayo
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$312.00
from $312.00 / night
Isle Be Back!
Summerland Key House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Child friendly
- Pet friendly
$280.00
from $280.00 / night
Sailfish Manor
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 30 nights min
- Child friendly
- Pet friendly
$312.00
from $312.00 / night
Reel Paradise
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 28 nights min
- Swimming pool
- Child friendly
- Air conditioning
$285.00
from $285.00 / night
The Pointe
Summerland Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Child friendly
- Air conditioning
- Pet friendly
$207.00
from $207.00 / night
Your search has been expanded 9.6 miles to include more rentals
Angelfish Cove
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
$159.00
from $159.00 / 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
$175.00
from $175.00 / 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
$234.00
from $234.00 / 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
$129.00
from $129.00 / night
Breeze Swept
Big Pine Key House - 6.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$230.00
from $230.00 / night
Island Time (both halves of duplex)
Big Pine Key House - 6.1 miles away
- 5 bedrooms 5
- 2 bathrooms
- sleeps 10 10
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$236.00
from $236.00 / 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
$110.00
from $110.00 / night
Island Time 1 (half of duplex)
Big Pine Key House - 6.4 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$125.00
from $125.00 / 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
$129.00
from $129.00 / night
Margarita 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
- Pet friendly
$160.00
from $160.00 / 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
$120.00
from $120.00 / 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
$101.00
from $101.00 / 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
$154.00
from $154.00 / 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
$242.00
from $242.00 / 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
$207.00
from $207.00 / 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
$140.00
from $140.00 / 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
$177.00
from $177.00 / 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
$184.00
from $184.00 / 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
$160.00
from $160.00 / 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
$125.00
from $125.00 / 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
$157.00
from $157.00 / 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
$144.00
from $144.00 / night
Ocean View Estate with Private Pool 15 minutes from Key West
Key West House - 3.6 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 10 10
- min stay varies
- Nearest beach 10 mi
- Swimming pool
- Child friendly
Responds fast! Avg. 3 hours 37 minutes
$544.00
from $544.00 / 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
$124.00
from $124.00 / 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
$257.00
from $257.00 / night
Hideaway Bay
Big Pine Key House - 5.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 31 nights min
- Child friendly
- Air conditioning
- Pet friendly
$127.00
from $127.00 / night
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