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Waterfront holiday rentals in Florida Keys

Find and book unique waterfront rentals on Airbnb

Top-rated waterfront rentals in Florida Keys

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, 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 Jul

$254 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!

27 Jul – 3 Aug

$313 SGD per night

Guest favourite

Flat 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

$247 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

27 Sep – 4 Oct

$287 SGD per night

Guest favourite

Apartment in Key Colony Beach

4.96 out of 5 average rating, 171 reviews

Oceanfront Sunrise Condo Private Beach Heated Pool

Impeccable condo directly on the ocean with water views from every window. Located in Key Colony Beach (middle Keys) with heated pool and private beach. Unit #20 is a studio condo with a classic Keys interior: newly renovated bathroom and crisp white kitchen stocked with everything needed to cook a complete meal (stove, oven, toaster, microwave, blender, fridge, etc). Enjoy the private back balcony and private beach with lounge chairs, patio tables, tiki's and BBQ grills for guest use.

29 Dec – 5 Jan

$756 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.

3–10 Sep

$242 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.

28 Jan – 4 Feb

$260 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

$567 SGD per night

Guest favourite

Cottage in Miami Lakes

4.98 out of 5 average rating, 167 reviews

* Lake Cottage * SpaLike Bath *

The cottage is centrally located in the serene hidden gem of Mia Lakes. Perfect for couples, solo adventurers or business travelers. You will feel hidden away from it all but yet only 5- 10 min walk from restaurants, shopping, groceries, movie theater, spa, gym etc. Our lakefront guest cottage is surrounded by lots of native plants, trees & wild life. You may swim, fish (catch & release) on the lake, as well as use of a paddle board & kayak.

23–30 Aug

$170 SGD per night

Guest favourite

Guest house in Key Largo

4.91 out of 5 average rating, 190 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.

23–30 Sep

$282 SGD per night

Guest favourite

Boat in Miami

4.98 out of 5 average rating, 694 reviews

Hunter 26 Sailboat

A one-of-a-kind experience for those who want to enjoy Miami from a different perspective. Can accommodate up to two people, includes a basic toilet and freshwater. The boat is anchored in Key Biscayne Bay, which allows you to view the Miami skyline from a distance. You'll be in the famous Coconut Grove area. I will be taking you from the dinghy dock to the boat. Two kayaks are included for guests.

18–25 Jun

$190 SGD per night

Guest favourite

Guest suite in Tavernier

4.97 out of 5 average rating, 246 reviews

POOL ! Key Largo! Tavernier! Welcome to Paradise!

POOL! A perfect tropical getaway! Life is good today! Bright, airy, 500 plus sq ft., canal front studio, close to the bay. From the dock you can KAYAK to mangrove tunnels, fish, or just relax. Cold drink in your hand, life is good today! You are going to have an awesome vacation!! ( NOTE: THE POOL MAY BE SHARED ON OCCASION, WITH OUR FAMILY. A SIGNED LIABILITY RELEASE IS REQUIRED AT CHECK IN )

10–17 Jul

$398 SGD per night

Holiday rentals for every style

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Houses

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Villas

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Popular amenities for waterfront rentals in Florida Keys

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Flat in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

12–19 Oct

$409 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

14–21 Nov

$433 SGD per night

Guest favourite

Flat in Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

10–17 Apr

$522 SGD per night

Guest favourite

Flat in Marco Island

4.94 out of 5 average rating, 173 reviews

Backwater Paradise

25 Oct – 1 Nov

$442 SGD per night

Guest favourite

Flat in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

25 Dec – 1 Jan

$490 SGD per night

Guest favourite

Flat in Miami

4.92 out of 5 average rating, 122 reviews

Penthouse 1908 Ocean Front View 1BD Monte Carlo

6–13 Jun

$716 SGD per night

Flat in Miami

4.83 out of 5 average rating, 289 reviews

Ocean Drive Oasis Art Deco South Beach Suite

10–17 May

$177 SGD per night

Guest favourite

Flat in Key West

4.89 out of 5 average rating, 135 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

7–14 Mar

$1,049 SGD per night

Waterfront house rentals

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 117 reviews

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

22–29 May

$788 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

28 Mar – 4 Apr

$400 SGD per night

Guest favourite

Home in Tavernier

4.87 out of 5 average rating, 207 reviews

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

9–16 Jul

$579 SGD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

31 Aug – 7 Sep

$1,122 SGD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 49 reviews

The Paradise 2

20–27 Mar

$528 SGD per night

Guest favourite

Home in Key Largo

4.97 out of 5 average rating, 32 reviews

Treetops

5–12 Sep

$427 SGD per night

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

$1,436 SGD per night

Guest favourite

Home in Key Colony Beach

5.0 out of 5 average rating, 96 reviews

ABeachBungalow-60’dock w/ access to pool and beach

22 Feb – 1 Mar

$635 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 Oct

$323 SGD per night

Guest favourite

Apartment in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

19–26 Jul

$382 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

29 Sep – 6 Oct

$581 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

13–20 Dec

$548 SGD per night

Guest favourite

Apartment in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

23–30 Aug

$796 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

5–12 Aug

$679 SGD per night

Guest favourite

Apartment in Palmetto Bay

4.89 out of 5 average rating, 197 reviews

Bright Modern Studio Apartment

23–30 Oct

$143 SGD per night

Guest favourite

Apartment in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

11–18 Nov

$938 SGD per night

Destinations to explore