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Islamorada Vacation Rentals

Islamorada Vacation Rentals & House Rentals with Swimming Pool - 45 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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Apartment (11)
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

45 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 / 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

$573.00

from $573.00 / night

Book

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

$429.00

Excellent (8 reviews)

from $429.00 / night

Book

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 / 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

Book

1 / 25

PALMS 309

Islamorada House

2 bedrooms 2
2 bathrooms
sleeps 5 5
min stay varies

Swimming pool
Ask about children

$85.00

Excellent (2 reviews)

from $85.00 / 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

$110.00

Excellent (3 reviews)

from $110.00 / 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

$157.00

Excellent (2 reviews)

from $157.00 / 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

$225.00

Excellent (14 reviews)

from $225.00 / 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

$245.00

Excellent (1 reviews)

from $245.00 / 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

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

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

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 / 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

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 / 16

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

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

PALMS 417

Islamorada Apartment

1 bedroom 1
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$70.00

Excellent (1 reviews)

from $70.00 / 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 / 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 / 29

PALMS 407

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 4 4
min stay varies

Swimming pool
Ask about children

$100.00

from $100.00 / night

Inquire

1 / 24

PALMS 301

Islamorada Apartment

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children

$76.00

Very Good (1 reviews)

from $76.00 / night

Inquire

Your search has been expanded 18.6 miles to include more rentals

1 / 17

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

“My family and I had a fabulous time. Enjoyed all the perks available. Close to a local shopping center which has everything you may need. We will be back...”

- Review left on 12/02/2016

$270.00

Excellent (4 reviews)

from $270.00 / night

Book

1 / 27

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

Excellent (1 reviews)

from $184.00 / night

Book

1 / 39

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

“Our family of 4 stayed here over Thanksgiving week and had the best time. Penny is very organized and everything was perfect, love the ambiance. We love the old Florida feel and the tiki hut is the best. Our teenage boys had a fantastic time swimming...”

- Review left on 04/14/2016

$161.00

Excellent (18 reviews)

from $161.00 / night

Book

1 / 24

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

Book

1 / 14

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

Inquire

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

$300.00

Very Good (27 reviews)

from $300.00 / night

Inquire

1 / 25

ROCK HARBOR CLUB P-8

Key Largo House - 10.3 miles away

2 bedrooms 2
2 bathrooms
sleeps 6 6
min stay varies

Swimming pool
Ask about children

$95.00

Very Good (2 reviews)

from $95.00 / 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

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

Inquire

1 / 1

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

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

Inquire

1 / 28

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

Excellent (1 reviews)

from $146.00 / night

Inquire

1 / 15

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

Excellent (3 reviews)

from $150.00 / night

Inquire

1 / 24

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

Very Good (2 reviews)

from $316.00 / night

Inquire

1 / 22

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

Very Good (3 reviews)

from $150.00 / night

Inquire

1 / 25

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

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

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

Book

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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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