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Islamorada Vacation Rentals

Islamorada Vacation Rentals & House Rentals with Swimming Pool - 44 Rentals Available.

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Air conditioning (2)
Balcony or terrace (19)
DVD player (2)
Dishwasher (2)
Fireplace (1)
Garden (1)
Grill (21)
Heated pool (8)
High Speed Internet (18)
Hot tub/Jacuzzi (13)
Private pool (8)
Swimming pool (21)
Washing machine (2)
Wi-Fi available (1)

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Apartment (12)
Condo (1)
House (8)

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44 Vacation rentals

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Filters applied: Swimming pool

Distance calculated in a straight line, road distances may differ. Confirm exact location with the property owner/manager.

1 / 27

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

Responds fast! Avg. 2 hours 35 minutes

“This house is the best!!!!! We had two familys staying and was perfect. The separate living quarters made our trip very enjoyable and very roomy. The house upstairs is remarkable and very up to date as well as downstairs. The back yard is your own...”

- Review left on 08/09/2016

$429.00

Excellent (19 reviews)

from $429.00 / night

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1 / 14

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

“Had a great time. Beautiful house. Very convenient to everything. We highly recommend this property...”

- Review left on 08/05/2016

$533.00

Excellent (9 reviews)

from $533.00 / night

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1 / 21

BEACON REEF 310

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$114.00

Excellent (5 reviews)

from $114.00 / night

Inquire

1 / 24

LYONS LANDING

Islamorada House

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$262.00

Excellent (1 reviews)

from $262.00 / night

Inquire

1 / 25

PALMS 309

Islamorada House

2 bedrooms 2
2 bathrooms
sleeps 5 5
30 nights min

Swimming pool
Ask about children

$86.00

Excellent (2 reviews)

from $86.00 / night

Inquire

1 / 25

BROCK HAUS ON THE GULF

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
7 nights min

Swimming pool
Ask about children

$211.00

Excellent (21 reviews)

from $211.00 / night

Inquire

1 / 24

PALMS 314

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
30 nights min

Swimming pool
Ask about children

$80.00

Excellent (2 reviews)

from $80.00 / night

Inquire

1 / 25

THE PALMS 405 - 93

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
30 nights min

Swimming pool
Ask about children

$120.00

from $120.00 / night

Inquire

1 / 20

FLAMINGO COTTAGE

Islamorada House

2 bedrooms 2
2 bathrooms
sleeps 6 6
30 nights min

Swimming pool
Ask about children
Pet friendly

$100.00

Excellent (1 reviews)

from $100.00 / night

Inquire

1 / 24

HOUSE DORADO

Islamorada House

3 bedrooms 3
3 bathrooms
sleeps 8 8
30 nights min

Swimming pool
Ask about children

$617.00

Excellent (2 reviews)

from $617.00 / night

Inquire

1 / 25

BEACON REEF 222

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$147.00

Excellent (2 reviews)

from $147.00 / night

Inquire

1 / 25

PALMS 402

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$80.00

from $80.00 / night

Inquire

1 / 26

BLUE WATER RETREAT

Islamorada House

3 bedrooms 3
3 bathrooms
sleeps 8 8
30 nights min

Swimming pool
Ask about children
Pet friendly

$184.00

Very Good (3 reviews)

from $184.00 / night

Inquire

1 / 25

BEACON REEF 501

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$110.00

Excellent (2 reviews)

from $110.00 / night

Inquire

1 / 25

MANATEE MANOR

Islamorada House

3 bedrooms 3
2 bathrooms
sleeps 8 8
30 nights min

Swimming pool
Ask about children
Pet friendly

$199.00

Excellent (2 reviews)

from $199.00 / night

Inquire

1 / 25

PALMS 407

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$80.00

from $80.00 / night

Inquire

1 / 24

PALMS 417

Islamorada Apartment

1 bedroom 1
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$70.00

Excellent (1 reviews)

from $70.00 / night

Inquire

1 / 24

PALMS 301

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
30 nights min

Swimming pool
Ask about children

$77.00

Very Good (1 reviews)

from $77.00 / night

Inquire

1 / 25

BEACON REEF 306

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$100.00

from $100.00 / night

Inquire

1 / 25

PALMS 317

Islamorada Apartment

1 bedroom 1
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$64.00

from $64.00 / night

Inquire

1 / 28

PALMS 404

Islamorada Condo

2 bedrooms 2
2 bathrooms
sleeps 6 6
30 nights min

Swimming pool
Ask about children

$77.00

from $77.00 / night

Inquire

Your search has been expanded 16.9 miles to include more rentals

1 / 17

Large Waterfront 4 balcony Key Largo Townhouse with Oceanfront Dock

Key Largo Townhouse - 11.4 miles away

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Nearest beach 0.01 mi
Swimming pool

“Norm was thorough in the walk through of the property we stayed. Townhouse condo was clean and well stocked. Next to salt water lagoon and pool. All the water toys were made available like snorkels, fins, fishing rods, kayaks and paddleboards. Golf...”

- Review left on 03/25/2017

$287.00

Average (5 reviews)

from $287.00 / night

Book

1 / 30

Key Largo Rental Fantastic Views

Key Largo Condo - 11.5 miles away

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Beach/lakeside relaxation
Swimming pool
Child friendly

“We have been coming to Key Largo for the past three years and by far this was our most enjoyable stay. We are looking forward to returning next year. You could not asked for a better host than Norman. Very accommodating. The location is excellent...”

- Review left on 05/15/2017

$287.00

Very Good (25 reviews)

from $287.00 / night

Book

1 / 16

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

“This place was awesome-everything included we had paddle boards, Kayaks, golf cart and bicycles. The host Norman couldn't have been more friendly and helpful. I recommend this getaway to anyone and it is pet friendly...”

- Review left on 01/19/2017

$401.00

Very Good (27 reviews)

from $401.00 / night

Book

1 / 28

Exquisite Ocean View Pool Home with Hot Tub and 40 foot Dock

Key Largo House - 11.7 miles away

4 bedrooms 4
2 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Child friendly
Air conditioning

$258.00

Excellent (3 reviews)

from $258.00 / night

Inquire

1 / 25

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

Inquire

1 / 25

BEACON REEF 522

Matecumbe Key Condo - 3.7 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$147.00

Excellent (2 reviews)

from $147.00 / night

Inquire

1 / 25

BEACON REEF 406

Matecumbe Key Condo - 3.7 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$100.00

Excellent (1 reviews)

from $100.00 / night

Inquire

1 / 25

TWICE THE CHARM

Key Largo House - 11.7 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$184.00

from $184.00 / night

Inquire

1 / 25

PALM HARBOR

Tavernier House - 3.9 miles away

4 bedrooms 4
3 bathrooms
sleeps 8 8
30 nights min

Swimming pool
Ask about children
Pet friendly

$333.00

from $333.00 / night

Inquire

1 / 25

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

Excellent (2 reviews)

from $140.00 / night

Inquire

1 / 25

PALMS 313

Matecumbe Key Condo - 7 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$74.00

from $74.00 / night

Inquire

1 / 24

CONCH BAR SOUTH

Tavernier House - 2.3 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$317.00

Very Good (3 reviews)

from $317.00 / night

Inquire

1 / 26

TROPICAL OASIS

Key Largo House - 11.9 miles away

4 bedrooms 4
4 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$292.00

from $292.00 / night

Inquire

1 / 18

MOON BAY A206

Key Largo Apartment - 16.9 miles away

2 bedrooms 2
1 bathroom
sleeps 6 6
30 nights min

Swimming pool
Ask about children

$105.00

Excellent (3 reviews)

from $105.00 / night

Inquire

1 / 25

PLANTATION ADVENTURE

Tavernier House - 3.3 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$217.00

Excellent (1 reviews)

from $217.00 / night

Inquire

1 / 22

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

Inquire

1 / 25

BEACON REEF 301

Matecumbe Key Condo - 3.7 miles away

2 bedrooms 2
2 bathrooms
sleeps 4 4
30 nights min

Swimming pool
Ask about children

$117.00

from $117.00 / night

Inquire

1 / 25

FISH WHISTLE

Matecumbe Key Villa - 1.6 miles away

4 bedrooms 4
3 bathrooms
sleeps 10 10
30 nights min

Swimming pool
Ask about children
Pet friendly

$500.00

from $500.00 / night

Inquire

1 / 25

ROCK HARBOR CLUB P-8

Key Largo House - 10.3 miles away

2 bedrooms 2
2 bathrooms
sleeps 6 6
30 nights min

Swimming pool
Ask about children

$100.00

Very Good (2 reviews)

from $100.00 / night

Inquire

Page 1 of 2

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This is the estimated nightly price based on a weekly stay. Contact the advertiser to confirm the price - it varies depending on when you stay and how long for.

This is the estimated nightly price based on a weekly stay.

Estimated price per night based on a weekly stay. Owner fees of {FEE} per stay may apply.

This is the total cost of the stay for the dates and number of guests that you entered.

This price is an estimate based on the latest rate information available to us. Contact the advertiser to ask for the exact price, including any additional fees.

Rates for this rental are unknown, please contact the homeowner to confirm the rate.

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