Islamorada Vacation Rentals & House Rentals with Swimming Pool - 45 Rentals Available.
45 Vacation rentals
Filters applied: Swimming pool

Dream Home In The Keys
Islamorada House
- 5 bedrooms 5
- 3 bathrooms
- sleeps 12 12
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Ask about children
$573.00
from $573.00 / night

The PERFECT Escape with pool & jacuzzi
Islamorada House
- 4 bedrooms 4
- 4 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 3 mi
- Swimming pool
$429.00
from $429.00 / night

Beautiful Oceanfront, heated pool, free wifi
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 6 6
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$458.00
from $458.00 / night

Islamorada Luxury Home Ocean & Bay Access
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 7 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$533.00
from $533.00 / night


BEACON REEF 310
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$110.00
from $110.00 / night

MATECUMBE JEWEL
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$157.00
from $157.00 / night

BROCK HAUS ON THE GULF
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
$225.00
from $225.00 / night

LYONS LANDING
Islamorada House
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$245.00
from $245.00 / night


FLAMINGO COTTAGE
Islamorada House
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$100.00
from $100.00 / night

THE PALMS 405 - 93
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
$103.00
from $103.00 / night


HOUSE DORADO
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
$616.00
from $616.00 / night

BEACON REEF 222
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$146.00
from $146.00 / night


MANATEE MANOR
Islamorada House
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$198.00
from $198.00 / night


BEACON REEF 501
Islamorada Apartment
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$110.00
from $110.00 / night

BLUE WATER RETREAT
Islamorada House
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$183.00
from $183.00 / night


Your search has been expanded 18.6 miles to include more rentals

Tarpon Cove at Ocean Pointe Resort
Tavernier Condo - 5.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$270.00
from $270.00 / night

Paradise By The Bay
Key Largo House - 18.6 miles away
- 3 bedrooms 3
- 3 bathrooms
- sleeps 8 8
- 30 nights min
- Beach/lakeside relaxation
- Swimming pool
- Child friendly
$184.00
from $184.00 / night

Steps from the Water and Swimming with your own Boat Dock
Key Largo Cottage - 14.2 miles away
- 1 bedroom 1
- 1 bathroom
- sleeps 5 5
- 7 nights min
- Beach/lakeside relaxation
- Nearest beach 5 mi
- Swimming pool
$161.00
from $161.00 / night

Penthouse Sunsets and Tropical Breeze in Key Largo
Key Largo Condo - 11.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 3 mi
- Swimming pool
$201.00
from $201.00 / night

Equisite Ocean View Pool Home with Hot Tub Dock
Key Largo House - 11.7 miles away
- 4 bedrooms 4
- 2 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Child friendly
- Air conditioning
$300.00
from $300.00 / night

Key Largo Ocean Front Villa with Dock and Incredible views
Key Largo Villa - 11.2 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Beach/lakeside relaxation
- Nearest beach 0.01 mi
- Swimming pool
$300.00
from $300.00 / night

ROCK HARBOR CLUB P-8
Key Largo House - 10.3 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 6 6
- min stay varies
- Swimming pool
- Ask about children
$95.00
from $95.00 / night

KEY LARGO YACHT CLUB 8
Key Largo Apartment - 11.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Ask about children
- Pet friendly
$140.00
from $140.00 / night

TWICE THE CHARM
Key Largo House - 11.7 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$183.00
from $183.00 / night

KEY LARGO YACHT CLUB 20
Key Largo House - 11.6 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 6 6
- 30 nights min
- Swimming pool
- Ask about children
- Pet friendly
$174.00
from $174.00 / night

TROPICAL OASIS
Key Largo House - 11.9 miles away
- 4 bedrooms 4
- 4 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$291.00
from $291.00 / night

BEACON REEF 522
Matecumbe Key Condo - 3.7 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- min stay varies
- Swimming pool
- Ask about children
$146.00
from $146.00 / night

MOON BAY A206
Key Largo Apartment - 16.9 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 6 6
- 7 nights min
- Swimming pool
- Ask about children
$150.00
from $150.00 / night

CONCH BAR SOUTH
Tavernier House - 2.3 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 10 10
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$316.00
from $316.00 / night

MOON BAY A410
Key Largo Apartment - 11.5 miles away
- 2 bedrooms 2
- 1 bathroom
- sleeps 4 4
- 7 nights min
- Swimming pool
- Ask about children
$150.00
from $150.00 / night

PALM HARBOR
Tavernier House - 3.9 miles away
- 4 bedrooms 4
- 3 bathrooms
- sleeps 8 8
- min stay varies
- Swimming pool
- Ask about children
- Pet friendly
$332.00
from $332.00 / night

SUNSET HAMMOCK 4B
Tavernier Apartment - 3.8 miles away
- 2 bedrooms 2
- 2 bathrooms
- sleeps 4 4
- 60 nights min
- Swimming pool
- Ask about children
- Pet friendly
$142.00
from $142.00 / night

87200OH-A7. Beautiful Florida Keys 3 Bedroom Town Home with Private Beach Access
Matecumbe Key House - 0.1 miles away
- 3 bedrooms 3
- 2 bathrooms
- sleeps 8 8
- 28 nights min
- Swimming pool
- Child friendly
- Air conditioning
$169.00
from $169.00 / night
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