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Search results; Over 1,000 homes in Islamorada

Top guest favourite

Boat in Islamorada

360 DEGREE WATERVIEW HOUSEBOAT

1 bedroom, 1 bed, 1 private bathroom

9–14 Jul

$1,294 SGD for 5 nights

,

4.93 out of 5 average rating, 385 reviews

Superhost

Villa in Islamorada

Private Beach & Dock / Heated Pool / Dolphin Key

4 bedrooms, 4 king beds, 4 bathrooms

13–18 Jul

New home discount

New place to stay

Guest favourite

Home in Islamorada

Islamorada Bungalow # 5

2 bedrooms, 2 beds, 1 bathroom

9–14 Aug

$2,398 SGD for 5 nights

Free cancellation

4.86 out of 5 average rating, 35 reviews

Home in Marathon

NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip

5 bedrooms, 6 beds, 4 bathrooms

11–18 Aug

Book early to save

New place to stay

Top guest favourite

Home in Duck Key

Private Pool Tropical Oasis - Centrally Located

3 bedrooms, 5 beds, 2.5 bathrooms

19–24 Sept

$3,363 SGD for 5 nights

5.0 out of 5 average rating, 110 reviews

Top guest favourite

Home in Islamorada

Flakey's

2 bedrooms, 3 beds, 1 bathroom

25 Jul – 1 Aug

$2,734 SGD for 7 nights

4.97 out of 5 average rating, 214 reviews

Guest favourite

Home in Islamorada

Summer-Fall Super Discounts- Check Availability!

4 bedrooms, 5 beds, 4.5 bathrooms

6–13 Jul

$9,275 SGD for 7 nights

5.0 out of 5 average rating, 7 reviews

Top guest favourite

Home in Islamorada

Waterfront private home, pool, dock, sunsets, tiki

4 bedrooms, 4 beds, 3 bathrooms

4–11 Sept

$11,770 SGD for 7 nights

5.0 out of 5 average rating, 52 reviews

Top guest favourite

Home in Islamorada

Seaside Sanctuary in Islamorada

4 bedrooms, 5 beds, 4.5 bathrooms

17–24 Jul

$10,616 SGD for 7 nights

4.96 out of 5 average rating, 25 reviews

Top guest favourite

Townhouse in Islamorada

Family Keys Escape: Speakeasy·Dock·Pool·BBQ Patio

3 bedrooms, 4 beds, 3 bathrooms

9–15 Aug

$4,322 SGD for 6 nights

5.0 out of 5 average rating, 14 reviews

Guest favourite

Home in Islamorada

The Villa by the Bay Pool/Boat Dock, Islamorada Fl

4 bedrooms, 5 beds, 3.5 bathrooms

10–17 Jul

$9,660 SGD for 7 nights

5.0 out of 5 average rating, 11 reviews

Top guest favourite

Home in Marathon

Luxury Boating Paradise+Pool+Sailing Kayaks

4 bedrooms, 8 beds, 3 bathrooms

15–22 Aug

$5,956 SGD for 7 nights

5.0 out of 5 average rating, 84 reviews

Home in Islamorada

Margaritaville

3 bedrooms, 3 beds, 2 bathrooms

30 Jul – 4 Aug

$1,631 SGD for 5 nights

4.88 out of 5 average rating, 8 reviews

Guest favourite

Home in Marathon

Paradise Villa: a luxury retreat

7 bedrooms, 8 beds, 7.5 bathrooms

8–15 Sept

$13,243 SGD for 7 nights

4.88 out of 5 average rating, 34 reviews

Guest favourite

Villa in Islamorada

Angler’s Reef home • Pool • Kayaks • Paddle boards

2 bedrooms, 4 beds, 2.5 bathrooms

7–14 Jul

$4,964 SGD for 7 nights

4.92 out of 5 average rating, 24 reviews

Featured hotel

Hotel in Islamorada

Matacumbe courtyard view room two queens Lanai

1 bedroom, 2 queen beds, 1 bathroom

19–24 Jul

$1,851 SGD for 5 nights

+$206 SGD Airbnb credit

Top guest favourite

Home in Marathon

World-Class Oceanfront Pool/Hottub Sunset Escape

5 bedrooms, 7 beds, 3.5 bathrooms

29 Aug – 5 Sept

5.0 out of 5 average rating, 37 reviews

Guest favourite

Home in Key Largo

Key Largo Paradise - MM100 Oceanside. Pool + Golf

3 bedrooms, 6 beds, 2 bathrooms

9–14 Sept

$3,121 SGD for 5 nights

5.0 out of 5 average rating, 7 reviews

Guest favourite

Home in Marathon

Beach House in Marathon with Amazing Backyard!

2 bedrooms, 4 beds, 2 bathrooms

25 Aug – 1 Sept

$3,943 SGD for 7 nights

Free cancellation

5.0 out of 5 average rating, 8 reviews