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Waterfront holiday rentals in Islamorada

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Islamorada

Guests agree: these waterfront rentals are highly rated for location, cleanliness and more.

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Holiday home in Key Largo

4.84 out of 5 average rating, 254 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.

6–13 Jun

$240 SGD per night

Guest favourite

Apartment 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!

29 Sep – 6 Oct

$360 SGD per night

Guest favourite

Apartment 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.

1–8 Oct

$580 SGD per night

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 208 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

25 Jul – 1 Aug

$589 SGD per night

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

11–18 Oct

$291 SGD per night

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.

25 Jan – 1 Feb

$270 SGD per night

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.

8–15 Nov

$260 SGD per night

Guest favourite

Apartment 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 Oct – 4 Nov

$474 SGD per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Conveniently located at MM 92.5, approximately 1 hour drive from Miami, you can enjoy a modern, newly redecorated Keys escape with amazing views of the sunrise right from your oceanside balcony. 2 bed/2 bath with full kitchen and washer/dryer. Pool, beach, pier, BBQ area, and private boat marina within this private community. Kayaks, paddle boards and bikes available for rent. No need to leave, but grocery stores, spas and ample restaurants are close by to fill any need.

5–12 Nov

$499 SGD per night

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.

24–31 Aug

$566 SGD per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 192 reviews

Oceanside, 1 bedroom, Bungalow in Key Largo

Canal front bungalow with beautiful views of the ocean. Private water front and pergola with steamer chairs and hammock. BBQ your fresh catch while lounging on the back porch, relaxing in the tropical landscape. One bedroom with Queen bed. Queen size pull-out couch in the living-room. Full kitchen boasting high-end appliances. One Car Parking by unit. Centrally located between shopping centers and destination activities.

10–17 Dec

$281 SGD per night

Guest favourite

Home in Islamorada

4.98 out of 5 average rating, 140 reviews

Porter’s Corner

Very quiet place with almost no neighbors on a deep water canal with excellent fishing and bayside access. 30 feet of dock to park a boat or just enjoy sunsets over the lagoon and watch the resident family of manatees. Walking distance to a beach, convenience store and a fish market with fresh local seafood. The entire property is 100% solar powered. The house is a duplex and I live on one side.

26 Apr – 3 May

$688 SGD per night

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 waterfront rentals in Islamorada

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 229 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

30 Jul – 6 Aug

$333 SGD per night

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

4–11 Aug

$507 SGD per night

Guest favourite

Flat in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

3–10 Apr

$415 SGD per night

Guest favourite

Flat in Key Largo

4.89 out of 5 average rating, 206 reviews

Seaside Vista - Ocean Front 2/1 with dockage

27 Sep – 4 Oct

$340 SGD per night

Guest favourite

Flat in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

18–25 Jun

$432 SGD per night

Guest favourite

Flat in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

12–19 Nov

$225 SGD per night

Guest favourite

Flat in Tavernier

5.0 out of 5 average rating, 13 reviews

Turtles Nest 2 Ocean Point condo

10–17 Jan

$474 SGD per night

Guest favourite

Flat in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

14–21 Dec

$321 SGD per night

Waterfront house rentals

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 118 reviews

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

3–10 Dec

$889 SGD per night

Guest favourite

Home in Key Largo

4.96 out of 5 average rating, 135 reviews

Key Largo Waterfront Home with Tiki & Boat Dock

26 Sep – 3 Oct

$399 SGD per night

Guest favourite

Home in Islamorada

4.94 out of 5 average rating, 18 reviews

3 Lux Ensuites Walk/Boat Island!

22–29 Mar

$793 SGD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

20–27 Mar

$539 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

$1,120 SGD per night

Guest favourite

Home in Key Largo

4.97 out of 5 average rating, 32 reviews

Treetops

9–14 Sep

$422 SGD per night

Guest favourite

Home in Islamorada

5.0 out of 5 average rating, 10 reviews

Heart of Islamorada ~ Private Boat Slip

9–16 Sep

$1,300 SGD per night

Guest favourite

Home in Key Colony Beach

4.98 out of 5 average rating, 51 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

3–10 Oct

$353 SGD per night

Waterfront apartment rentals

Guest favourite

Apartment in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

22–29 Aug

$323 SGD per night

Guest favourite

Apartment in Tavernier

4.93 out of 5 average rating, 133 reviews

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

20–27 Dec

$584 SGD per night

Guest favourite

Apartment in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

7–14 Nov

$677 SGD per night

Guest favourite

Apartment in Tavernier

4.91 out of 5 average rating, 111 reviews

500 Burton Drive Tavernier, Key Largo

15–22 Apr

$423 SGD per night

Guest favourite

Apartment in Tavernier

4.87 out of 5 average rating, 126 reviews

Reel Large END Unit in Ocean Point Suites

3–10 Jul

$534 SGD per night

Guest favourite

Apartment in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

18–25 Feb

$937 SGD per night

Apartment in Tavernier

4.8 out of 5 average rating, 130 reviews

TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'

23–30 Oct

$333 SGD per night

Guest favourite

Apartment in Key Largo

4.91 out of 5 average rating, 104 reviews

Relaxing Spacious Waterfront Key Largo #1 Sunsets!

20–27 Apr

$397 SGD per night

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
$82 SGD before taxes and fees

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