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Waterfront holiday rentals in Islamorada

Find and book unique waterfront accommodation on Airbnb

Top-rated waterfront accommodation in Islamorada

Guests agree: These waterfront accommodation options are highly rated for location, cleanliness and more.

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Holiday home in Key Largo

4.84 out of 5 average rating, 252 reviews

Charming Waterside Cabana in Key Largo | Cabana 4

Enjoy water front living in Key Largo! Watch the boats go by with fresh catch served daily at the local restaurants. See manatees, nurse sharks and fish swim by the canal all day. Dock your boat at the Pilot House Marina just down the street. Our unit is Modern, Spacious and Spotless with Private Parking, Fast Wifi, Netflix, Cold AC, Plush Pillows and a Cozy bed. We are on a main canal to open ocean. Near Rodriguez Key, Mosquito Bank, Christ of the Abyss and many sunken shipwrecks for exploring.

18 – 25 July

$2,355 AUD total

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Welcome to our remodeled costal 1BR 1 Bath condo nestled in the premier oceanfront complex in Tavernier, FL. Escape to paradise and enjoy the wonderful Ocean views from the private balcony while just a few steps away from the sunny private beach, marina, minutes away from restaurants, shops, and attractions. ✔ Comfortable Queen BR ✔ Open Design Living ✔ Fully Equipped Kitchen ✔ Balcony ✔ Smart TVs/WI FI ✔ Complex Amenities (Pool, Hot Tub, Marina, BBQ, Sports, Free Parking) Learn more below!

4 – 11 July

$3,058 AUD total

Guest favourite

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

***IMPORTANT*** The pictures you see here are of OUR unit. What you see is what YOU GET. No surprise when you arrive at Ocean Pointe. NO bait and switch. We own in the Prominent Building #3 just steps from the Pool & Jacuzzi. Wireless Internet Netflix & Cable TV, XBOX ONE. ***Most of our guests (99%) claim this is the cleanest Airbnb they have ever stayed in.*** You will get a TRUE UNIMPEDED OCEAN VIEW in our unit. Read our reviews, our past guests tell it all. ⭐ 5 STAR ⭐ Get what you pay for.

18 – 25 Aug

$5,220 AUD total

Guest favourite

Cottage in Islamorada

4.94 out of 5 average rating, 16 reviews

Waterfront Cottage Walk to World Famous Lorelei

Waterfront Conch Cottage. Short walk to world famous Lorelei for sunset celebrations. Custom length of stays can be arranged if booking a sandbar/sunset/fishing charter with our family business. The cottage was built in 1940s and still has the original hardwood floors, open beam ceilings. Private yet in the heart of Islamorada. Walk to two local craft breweries nearby! This listing is new to AIRBNB but booked for many reservations thru VRBO all 5 star. One pet only under 20lbs. /pet fee $150

1 – 8 Sept

$3,398 AUD total

Guest favourite

Condo in Tavernier

4.93 out of 5 average rating, 133 reviews

It's Tiki Time! Top Floor SeaView Mid-Mod 1 Br/1Ba

Stay at our tropical hideaway rated one the “Coolest Airbnb’s in the Keys” by Trips to Discover! Our romantic condominium (sleeps 4) is located at the gated Ocean Pointe resort in the nature isle of Tavernier. You'll love the colorful mid-century modern decor that reflects the shades of this Keys paradise in the American Caribbean. With 60+ pristine acres, Ocean Pointe is the perfect blend of natural beauty and modern-day luxury and convenience for a great couples or small family getaway .

30 Oct – 6 Nov

$3,301 AUD total

Guest favourite

Apartment in Key Largo

4.94 out of 5 average rating, 247 reviews

Waterfront Studio 1| Kayaks | Pool |Bay View |Wifi

Escape to Northern Key Largo for a relaxing vacation! Discover great restaurants, beautiful state parks, and marine life. This bright, modern studio boasts excellent views of Manatee Bay, free kayaks and paddle boards, and a full kitchen. With access to a swimming pool and docks, there’s always something to do. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park 22 Min Drive to African Queen Canal Cruise Experience Key Largo With Us & Learn More Below!

28 Oct – 4 Nov

$2,186 AUD total

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 207 reviews

Clean Houseboat w/ Great Wi-Fi,Luxury on the water

Very spacious, Comfortable and "super clean" Houseboat. Rent daily “Baycation” is a 44'x15' triple level upper deck Houseboat completely remodeled. This is an adventure, unlike any hotel room! Live on the water, in an amazing marina, with so much to do you need to come back! Sleep like you never have before, all my guests tell me that! Bonus Lay on the upper deck and see the amazing star ambiance...... This is for everyone......Couples, families & just friends, Its perfect

15 – 22 Aug

$4,829 AUD total

Guest favourite

Holiday home in Key Largo

4.99 out of 5 average rating, 145 reviews

Waterfront, GROUND LEVEL, Awesome Sunsets!!!

This ground level unique location is close to everything. Walk to some of the most iconic restaurants and bars Key Largo has to offer for fresh seafood and awesome drinks! We Do Not allow fishing on our Property! Dockage Available for additional fee! Enjoy the amazing sunsets over the water from your private porch and dock. John Pennekamp Coral Reef State Park close by. Walk to dolphin research center!! 28 day rental I am a licensed charter boat captain and offer discounts for all guests

26 Aug – 2 Sept

$2,802 AUD total

Cottage in Islamorada

4.81 out of 5 average rating, 143 reviews

FLOATING 1BD 1BA PRIVATE COTTAGE - MAKO

Tucked away in the vibrant Florida Keys, is our pristine paradise. We are located in the heart of Islamorada, where the weather is always gorgeous, the fishing never disappoints, and the sunsets are mesmerizing. If you are seeking a relaxing get away, look no further. Each unit is private, and the neighborhood is tucked off the beaten path. On site, you will have the luxury of renting your own private boat. Boat rentals are 20% off for guests! A 5% lodging tax will be charged on arrival.

8 – 15 Sept

$2,188 AUD total

Guest favourite

Boat in Islamorada

4.92 out of 5 average rating, 327 reviews

360 DEGREE WATERVIEW HOUSEBOAT

IMPORTANT Enjoy your own private retreat aboard a solar and wind powered houseboat moored 1/2 mile from land in the beautiful Islamorada Please do not arrive after dark and NO night riding. Need experience with hand pull outboard motors a 12 foot skiff with a 6hp outboard motor is provided reliable to go back and forth from shore NOT reliable for exploring No hot water on shower, heat water in Tpots or Solar bags. Please shave before arriving No suitcases, least amount of cloths.

28 Jan – 4 Feb

$2,297 AUD total

Guest favourite

Condo in Key Colony Beach

4.91 out of 5 average rating, 197 reviews

Oceanfront Breeze, Stunning Views, Beach/Pool

Newly renovated ocean front condo with gorgeous, unobstructed views from every window. Beautiful studio condo on the 1st floor only steps away from the private beach and heated pool. Condo features a fresh, clean interior with brand furnishings, bathroom and kitchen stocked with everything (dishes, cookware, utensils, glassware, stove, oven, toaster, microwave, blender, fridge, etc). Guests enjoy the quiet private beach with lounge chairs, patio tables, tiki's and BBQ grills.

28 July – 4 Aug

$4,188 AUD total

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 106 reviews

Sea Ray Cove , 75’ boat dock, 1 block from beach!

2024 - New Weber grill This ground level waterfront home has received a new face lift. Completely remodeled 3 bedroom with bonus room in the well known Sombrero Beach neighborhood. Just a short block walk to the sandy beach shore. Home has an open floor plan overlooking the in-ground pool deck and new tiki hut. Enjoy your morning coffee and happy hour in the screened-in porch with views of the wide lagoon. Come and create your family memories in the fabulous Keys.

17 – 24 Aug

$5,339 AUD total

Holiday rentals for every style

Get the amount of space that is right for you

Villas

Luxurious estates for the ultimate escape

Cottages

Quaint homes, peaceful surroundings

Houses

A space that's all yours, with room for everyone

Popular amenities for Islamorada waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment accommodation

Guest favourite

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

12 – 19 Dec

$3,723 AUD total

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

2 – 9 Mar

$5,159 AUD total

Guest favourite

Apartment in Key Largo

4.92 out of 5 average rating, 105 reviews

2/1 Oceanfront Apartment with Dockage

20 – 27 June

$3,939 AUD total

Guest favourite

Apartment in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

14 – 21 Nov

$3,798 AUD total

Guest favourite

Apartment in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

12 – 19 Nov

$2,107 AUD total

Guest favourite

Apartment in Tavernier

5.0 out of 5 average rating, 11 reviews

Turtles Nest 2 Ocean Point condo

10 – 17 July

$4,179 AUD total

Guest favourite

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

22 – 29 Sept

$3,088 AUD total

Apartment in Tavernier

4.84 out of 5 average rating, 32 reviews

Serene Oceanfront Keys Condo

1 – 8 Nov

$4,851 AUD total

Waterfront house rentals

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 135 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

28 Mar – 4 Apr

$3,444 AUD total

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

Marathon one-level home on the Marina - with slip!

12 – 19 Dec

$7,754 AUD total

Guest favourite

Home in Key Largo

4.88 out of 5 average rating, 163 reviews

Outdoor Paradise - Beach, Boats, Snorkeling & Sun!

15 – 22 Apr

$2,521 AUD total

Guest favourite

Home in Islamorada

4.94 out of 5 average rating, 17 reviews

3 Lux Ensuites Walk/Boat Island!

22 – 29 Mar

$6,981 AUD total

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sept

$10,384 AUD total

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 14 reviews

Private 1 Acre House~Private Beach~Tiki Hut~Dock

14 – 21 Oct

$10,890 AUD total

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 49 reviews

The Paradise 2

15 – 22 Jan

$4,373 AUD total

Guest favourite

Home in Islamorada

5.0 out of 5 average rating, 10 reviews

Heart of Islamorada ~ Private Boat Slip

28 Sept – 5 Oct

$11,253 AUD total

Waterfront condo accommodation

Condo in Key Colony Beach

4.8 out of 5 average rating, 107 reviews

Beachside Unit 28 - Private Beach, Pool & Paradise

4 – 11 Oct

$2,760 AUD total

Guest favourite

Condo in Tavernier

4.91 out of 5 average rating, 110 reviews

500 Burton Drive Tavernier, Key Largo

28 Sept – 5 Oct

$3,497 AUD total

Guest favourite

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

28 Nov – 5 Dec

$4,559 AUD total

Guest favourite

Condo in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

7 – 14 Feb

$6,173 AUD total

Guest favourite

Condo in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

11 – 18 Nov

$7,988 AUD total

Guest favourite

Condo in Tavernier

4.87 out of 5 average rating, 125 reviews

Reel Large END Unit in Ocean Point Suites

24 – 31 Mar

$5,026 AUD total

Guest favourite

Condo in Key Largo

4.91 out of 5 average rating, 104 reviews

Relaxing Spacious Waterfront Key Largo #1 Sunsets!

4 – 11 Oct

$3,668 AUD total

Condo in Tavernier

4.8 out of 5 average rating, 130 reviews

TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'

17 – 24 Mar

$4,055 AUD total

Quick stats about waterfront rentals in Islamorada

Total rentals
290 properties
Rentals with a pool
200 properties have a pool
Pet-friendly rentals
100 properties allow pets
Family-friendly rentals
240 properties are a good fit for families
Total number of reviews
2.7K reviews
Nightly prices starting at
$92 AUD before taxes and fees

Destinations to explore