Summerland Key Vacation Rentals & House Rentals - 58 Rentals Available
58 Vacation rentals
Caribbean Dream
Summerland Key House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Swimming pool
- Child friendly
- Air conditioning
$330.00
from $330.00 / 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
$150.00
from $150.00 / 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
$129.00
from $129.00 / night
Casa Turquesa
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$244.00
from $244.00 / night
Cruikshank
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
Blue Lagoon
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$221.00
from $221.00 / night
Villa Cayo
Summerland Key House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 30 nights min
- Ask about children
- Air conditioning
- Pet friendly
$297.00
from $297.00 / night
Isle Be Back!
Summerland Key House
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- 30 nights min
- Child friendly
- Pet friendly
$267.00
from $267.00 / night
Sailfish Manor
Summerland Key House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 9 9
- 30 nights min
- Child friendly
- Pet friendly
$297.00
from $297.00 / night
Caribbean Dream
Summerland Key House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- 30 nights min
- Child friendly
$430.00
from $430.00 / night
The Pointe
Summerland Key House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Child friendly
- Air conditioning
- Pet friendly
$197.00
from $197.00 / night
Your search has been expanded 9.6 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
$167.00
from $167.00 / 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
$104.00
from $104.00 / 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
$194.00
from $194.00 / 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
$114.00
from $114.00 / 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
$119.00
from $119.00 / 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
$154.00
from $154.00 / 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
$197.00
from $197.00 / 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
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
$142.00
from $142.00 / 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
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
Ramrod Retreat
Ramrod Key House - 2.5 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Air conditioning
- Pet friendly
$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
$145.00
from $145.00 / 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
$117.00
from $117.00 / 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
$114.00
from $114.00 / 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
Hawkins Heaven
Cudjoe Key House - 2.1 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 30 nights min
- Child friendly
$140.00
from $140.00 / night
Pelican Perch
Cudjoe Key House - 1.9 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
- Pet friendly
$160.00
from $160.00 / night
Sun Kissed
Ramrod Key House - 2.6 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Child friendly
$120.00
from $120.00 / 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
$121.00
from $121.00 / 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
$119.00
from $119.00 / 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
$94.00
from $94.00 / 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
$174.00
from $174.00 / 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
$227.00
from $227.00 / 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
$122.00
from $122.00 / night
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