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Search results; Over 1,000 homes in Islamorada

Houseboat in Islamorada

Perfect escape to the ocean

2 bedrooms, 3 beds, 1 bath

Nov 30 – Dec 5

ﺩ.ﺇ10,225 for 5 nights

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4.55 out of 5 average rating, 22 reviews

Home in Islamorada

Turtle Cove | Oceanfront w/Speakeasy, Dock & Pool

3 bedrooms4 beds,

Nov 16 – 22

ﺩ.ﺇ7,465 for 6 nights, originally ﺩ.ﺇ9,101

New place to stay

Home in Islamorada

Islamorada Bungalow # 5

2 bedrooms2 beds,

Nov 16 – 21

ﺩ.ﺇ6,103 for 5 nights, originally ﺩ.ﺇ7,305

5.0 out of 5 average rating, 3 reviews

Guest favorite

Cottage in Islamorada

2br/1ba w heated pool, 1 mile to robbies marina

2 bedrooms3 beds,

Nov 18 – 23

ﺩ.ﺇ4,852 for 5 nights

4.97 out of 5 average rating, 124 reviews

Top guest favorite

Home in Key Largo

Lakefront pool house, jacuzzi

3 bedrooms6 beds,

Jan 18 – 23

ﺩ.ﺇ13,589 for 5 nights

5.0 out of 5 average rating, 38 reviews

Hotel in Key Largo

Double Room with - Ocean View

1 bedroom1 bed,

May 3 – 8

ﺩ.ﺇ1,943 for 5 nights

4.75 out of 5 average rating, 20 reviews

Guest favorite

Condo in Tavernier

Sunshine Paradise Key Largo Ocean Pointe 4402

2 bedrooms4 beds,

Nov 16 – 21

ﺩ.ﺇ4,297 for 5 nights

4.97 out of 5 average rating, 76 reviews

Houseboat in Islamorada

Off-Grid Islamorada Stay

2 bedrooms4 beds,

Nov 16 – 21

ﺩ.ﺇ6,544 for 5 nights

Top guest favorite

Apartment in Islamorada

Hidden Gem Islamorada | 1st Floor

2 bedrooms2 beds,

Dec 13 – 18

ﺩ.ﺇ6,394 for 5 nights

4.97 out of 5 average rating, 78 reviews

Top guest favorite

Guesthouse in Key Largo

Seaside Bungalow

1 bedroom2 beds,

Jan 19 – 24

ﺩ.ﺇ4,267 for 5 nights

4.93 out of 5 average rating, 166 reviews

Home in Islamorada

Oceanfront Estate | Private Beach | Heated Pool

5 bedrooms5 beds,

Nov 18 – 25

ﺩ.ﺇ37,159 for 7 nights, originally ﺩ.ﺇ41,070

Villa in Duck Key

Waterfront villa for families * Family friendly*

2 bedrooms3 beds,

Nov 17 – 22

ﺩ.ﺇ3,574 for 5 nights, originally ﺩ.ﺇ5,777

4.78 out of 5 average rating, 119 reviews

Hotel in Islamorada

Check out the nearby fishing charters

1 bedroom2 queen beds,

Nov 16 – 21

ﺩ.ﺇ2,389 for 5 nights

4.29 out of 5 average rating, 24 reviews

Guest favorite

Bungalow in Islamorada

Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s

2 bedrooms3 beds,

Dec 14 – 19

ﺩ.ﺇ11,301 for 5 nights

4.97 out of 5 average rating, 61 reviews

Top guest favorite

Townhouse in Islamorada

NEW - Luxury Seascape w/Pool+Free Dockage+Gameroom

3 bedrooms

Nov 18 – 23

ﺩ.ﺇ6,878 for 5 nights, originally ﺩ.ﺇ8,689

4.92 out of 5 average rating, 12 reviews

Top guest favorite

Apartment in Tavernier

When Paradise is Key: Tropical Oceanfront Condo

2 bedrooms5 beds,

Dec 5 – 10

ﺩ.ﺇ5,274 for 5 nights

4.97 out of 5 average rating, 67 reviews

Top guest favorite

Home in Key Largo

Remodeled July 2025 2/2 Townhouse

2 bedrooms3 beds,

Nov 17 – 22

ﺩ.ﺇ5,382 for 5 nights, originally ﺩ.ﺇ7,218

5.0 out of 5 average rating, 12 reviews

Top guest favorite

Condo in Tavernier

Tequila Sunrise

2 bedrooms2 beds,

Nov 18 – 23

ﺩ.ﺇ5,821 for 5 nights

5.0 out of 5 average rating, 66 reviews

Top guest favorite

Home in Islamorada

4-Bedroom Coastal Retreat

4 bedrooms5 beds,

Nov 30 – Dec 7

ﺩ.ﺇ33,473 for 7 nights

5.0 out of 5 average rating, 8 reviews