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Islamorada Vacation Rentals

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

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Air conditioning (4)
Balcony or terrace (19)
DVD player (4)
Dishwasher (3)
Fireplace (1)
Garden (2)
Grill (22)
Heated pool (9)
High Speed Internet (20)
Hot tub/Jacuzzi (12)
Private pool (10)
Swimming pool (22)
Washing machine (4)
Wi-Fi available (2)

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House (11)

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To book this vacation rental you need to pay through the Vacation Home Rentals website. We can’t protect your payment if you don’t pay through us. Learn more

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 / 22

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

“We had four couples on our summer fishing vacation that we do every year in Islamorada.Couldnt have been better,we had couple days at first to go feed tarpon at Robbies and relax till seas calmed down and we got out in flat waters to fish,we caught...”

- Review left on 05/29/2015

$322.00

Excellent (7 reviews)

from $322.00 / night

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1 / 25

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

Responds fast! Avg. 3 hours 14 minutes

$358.00

from $358.00 / night

Book

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

$465.00

Excellent (9 reviews)

from $465.00 / night

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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

“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

$458.00

Excellent (19 reviews)

from $458.00 / night

Inquire

1 / 24

PALMS 214

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$76.00

Excellent (1 reviews)

from $76.00 / night

Inquire

1 / 21

BEACON REEF 310

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$106.00

Excellent (2 reviews)

from $106.00 / night

Inquire

1 / 25

PALMS 407

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$101.00

from $101.00 / night

Inquire

1 / 25

BROCK HAUS ON THE GULF

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children

$225.00

Excellent (13 reviews)

from $225.00 / night

Inquire

1 / 25

PALMS 417

Islamorada Apartment

1 bedroom 1
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$66.00

Excellent (1 reviews)

from $66.00 / night

Inquire

1 / 25

MATECUMBE JEWEL

Islamorada House

3 bedrooms 3
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children
Pet friendly

$150.00

Excellent (2 reviews)

from $150.00 / night

Inquire

1 / 25

FLAMINGO COTTAGE

Islamorada House

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children
Pet friendly

$101.00

from $101.00 / night

Inquire

1 / 24

HOUSE DORADO

Islamorada House

3 bedrooms 3
3 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Ask about children

$616.00

Excellent (2 reviews)

from $616.00 / night

Inquire

1 / 25

PALMS 309

Islamorada House

2 bedrooms 2
2 bathrooms
sleeps 5 5
min stay varies

Swimming pool
Ask about children

$81.00

Excellent (2 reviews)

from $81.00 / night

Inquire

1 / 25

BEACON REEF 222

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$146.00

Excellent (2 reviews)

from $146.00 / night

Inquire

1 / 25

PALMS 314

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 5 5
min stay varies

Swimming pool
Ask about children

$80.00

Excellent (2 reviews)

from $80.00 / night

Inquire

1 / 25

PALMS 402

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$80.00

from $80.00 / night

Inquire

1 / 25

BEACON REEF 501

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$110.00

Excellent (1 reviews)

from $110.00 / night

Inquire

1 / 24

PALMS 301

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children

$73.00

Very Good (1 reviews)

from $73.00 / night

Inquire

1 / 26

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

Very Good (3 reviews)

from $183.00 / night

Inquire

1 / 24

LYONS LANDING

Islamorada House

4 bedrooms 4
3 bathrooms
sleeps 10 10
min stay varies

Swimming pool
Ask about children
Pet friendly

$232.00

Excellent (2 reviews)

from $232.00 / night

Inquire

1 / 25

MANATEE MANOR

Islamorada House

3 bedrooms 3
2 bathrooms
sleeps 8 8
min stay varies

Swimming pool
Ask about children
Pet friendly

$198.00

Excellent (2 reviews)

from $198.00 / night

Inquire

1 / 25

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

Inquire

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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.

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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