Search results; Over 1,000 places in Islamorada

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Luxe
Home in Islamorada
Peninsula Villa | Heated Pool | Sunset Point
10 guests5 bedrooms7 beds4 baths
Jun 8 – 13
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Jun 8 – 13
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R344,495 ZAR for 5 nights
for 5 nights

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Top guest favorite
Boat in Islamorada
360 DEGREE WATERVIEW HOUSEBOAT
Free cancellation
Jun 7 – 12
R18,559 ZAR for 5 nights
for 5 nights
4.93 out of 5 average rating, 348 reviews
Top guest favorite
Home in Islamorada
Flakey's
3 beds
Jun 7 – 14
R37,564 ZAR for 7 nights
for 7 nights
4.97 out of 5 average rating, 192 reviews
Guest favorite
Home in Islamorada
Heart of Islamorada ~ Private Boat Slip
Free cancellation
Jul 5 – 10
R109,294 ZAR for 5 nights
for 5 nights
4.96 out of 5 average rating, 26 reviews
Houseboat in Islamorada
Perfect escape to the ocean
3 beds
Jun 8 – 13
R40,535 ZAR for 5 nights
for 5 nights
4.38 out of 5 average rating, 8 reviews
Top guest favorite
Cottage in Islamorada
Waterfront Cottage Walk to World Famous Lorelei
1 king bed
Sep 2 – 7
R28,104 ZAR for 5 nights
for 5 nights
4.95 out of 5 average rating, 41 reviews
Guest favorite
Bungalow in Islamorada
Castaway Island - Pool, Spa, Tiki Bar, Kyaks,Sup’s
3 beds
Jul 18 – 23
R61,730 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 53 reviews
Top guest favorite
Villa in Islamorada
Isla Key Lime: FREE Boat Dockage Sept-Oct Only!
3 beds
Jul 21 – 28
R80,866 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 7 reviews
Guest favorite
Home in Islamorada
Waterfront private home, pool, dock, sunsets, tiki
4 beds
Aug 16 – 23
R202,562 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 42 reviews
Apartment in Islamorada
Poolside 2 queen Apartment
Free cancellation
Jun 14 – 19
R21,378 ZAR for 5 nights
for 5 nights
4.77 out of 5 average rating, 44 reviews
Guest favorite
Home in Islamorada
The Villa by the Bay Unit 2 Private Pool/Boat Dock
Free cancellation
Jul 12 – 19
R146,057 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 8 reviews
Guest favorite
Houseboat in Islamorada
2/1 Aqua Lodge with Full Kitchen
Free cancellation
Jul 6 – 11
R22,696 ZAR for 5 nights
for 5 nights
4.87 out of 5 average rating, 23 reviews
Guest favorite
Apartment in Islamorada
Hidden Gem Islamorada | 1st Floor
Free cancellation
Aug 16 – 21
R31,647 ZAR for 5 nights
for 5 nights
4.98 out of 5 average rating, 65 reviews
Home in Islamorada
Bayview Beautiful townhouse in Islamorada, FL KEYS
5 beds
Jun 3 – 10
R45,073 ZAR for 7 nights
for 7 nights
Home in Islamorada
Oceanfront Estate in the Heart of Islamorada
5 beds
Jun 4 – 11
R179,232 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 3 reviews
Top guest favorite
Townhouse in Islamorada
Peacock Shores Islamorada - Vacation On The Beach!
Free cancellation
Jul 5 – 12
R53,323 ZAR for 7 nights
for 7 nights
4.98 out of 5 average rating, 55 reviews
Superhost
Hotel room in Islamorada
Fun Under the Sun! Beachfront, w/ Pool Onsite!
1 king bed
Jun 3 – 8
R36,814 ZAR for 5 nights
for 5 nights
Guest favorite
Home in Islamorada
Angler's Reef 4BD / 3.5 BATH - W/31' Boat Slip!
Free cancellation
Jul 5 – 12
R114,538 ZAR for 7 nights
for 7 nights
5.0 out of 5 average rating, 5 reviews
Villa in Islamorada
Scenic Resort w/ Outdoor Pool | Florida Keys Stay
2 king beds
Jun 3 – 8
R43,970 ZAR for 5 nights
for 5 nights
4.71 out of 5 average rating, 7 reviews