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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

$1,295 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

24–29 Jul

New home discount

New place to stay

Home in Islamorada

Margaritaville

3 bedrooms, 3 beds

5–10 Aug

$1,221 SGD for 5 nights

4.88 out of 5 average rating, 8 reviews

Guest favourite

Home in Islamorada

Islamorada Bungalow # 5

2 bedrooms, 2 beds

9–14 Aug

$2,399 SGD for 5 nights

Pay $0 today

Free cancellation

4.86 out of 5 average rating, 35 reviews

Guest favourite

Home in Islamorada

Summer-Fall Super Discounts- Check Availability!

4 bedrooms, 5 beds

7–14 Jul

$9,278 SGD for 7 nights

5.0 out of 5 average rating, 7 reviews

Flat in Islamorada

Poolside 2 queen Apartment

1 bedroom, 1 bed

13–18 Jul

Extended stay discount

Pay $0 today

Free cancellation

4.8 out of 5 average rating, 50 reviews

Home in Marathon

NEW! LUX VILLA 5 Beds 4 Baths Pool Boat Slip

5 bedrooms, 6 beds

22–29 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

19–24 Sept

$3,364 SGD for 5 nights

5.0 out of 5 average rating, 110 reviews

Top guest favourite

Home in Islamorada

Waterfront private home, pool, dock, sunsets, tiki

4 bedrooms, 4 beds

4–11 Sept

5.0 out of 5 average rating, 52 reviews

Home in Marathon

Updated 4BR view, pet friendly, private pool, dock

4 bedrooms, 7 beds

29 Aug – 5 Sept

$6,201 SGD for 7 nights

5.0 out of 5 average rating, 25 reviews

Guest favourite

Home in Islamorada

Island Paradise in Anglers Reef!

2 bedrooms, 3 beds

11–18 Jul

$3,788 SGD for 7 nights

Pay $0 today

Free cancellation

5.0 out of 5 average rating, 5 reviews

Superhost

Houseboat in Buttonwood Sound

Premium Floating Bungalow by Stay Ombi

1 bedroom, 1 king bed

12–17 Jul

Extended stay discount

4.91 out of 5 average rating, 34 reviews

Home in Marathon

Special-New Oceanfront Home-5Ksf under $1K a nite!

5 bedrooms, 5 beds

12–19 Jul

$10,746 SGD for 7 nights

Pay $0 today

Free cancellation

New place to stay

Top guest favourite

Home in Islamorada

Flakey's

2 bedrooms, 3 beds

25 Jul – 1 Aug

$2,735 SGD for 7 nights

4.97 out of 5 average rating, 214 reviews

Luxe

Home in Marathon

Ocean Palms Luxury Oceanfront SeaGlass Cove FLKeys

5 bedrooms

7–14 Jul

$10,592 SGD for 7 nights

Free cancellation

Featured hotel

Hotel in Islamorada

Matacumbe courtyard view room two queens Lanai

1 bedroom, 2 queen beds

19–24 Jul

$1,852 SGD for 5 nights

+$206 SGD Airbnb credit

Top guest favourite

Home in Marathon

Angler’s Terrace Conde Nast Traveler’s Best Airbnb

4 bedrooms, 6 beds

28 Nov – 5 Dec

4.97 out of 5 average rating, 145 reviews

Top guest favourite

Townhouse in Islamorada

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

3 bedrooms, 4 beds

9–15 Aug

$4,301 SGD for 6 nights

5.0 out of 5 average rating, 14 reviews

Superhost

Home in Islamorada

Private Beach | Heated Pool | Mahi Key

3 bedrooms, 3 king beds

18–25 Jul

4.9 out of 5 average rating, 10 reviews