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Waterfront vacation rentals in Key West

Find and book unique waterfront accommodations on Airbnb

Top-rated waterfront accommodations in Key West

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

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Vacation 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.

Jun. 23 – 30

$297 CAD per night

Guest favourite

Condo 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.

Nov. 13 – 20

$534 CAD 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.

Mar. 16 – 23

$311 CAD per night

Guest favourite

Cottage in Little Torch Key

4.91 out of 5 average rating, 146 reviews

Waterfront Cozy Cottage with Boat Ramp & Dock!

Welcome to Paradise! Stay in the amazing Keys and beautiful waterfront home with 250 foot dock, ramp, and basin for your boat. It's a must-see rustic outdoor environment and fishery experience, very typical in the Keys! The property lot is almost an acre with a work section and still very spacious. Stunning panoramic water views, sunrise and sunset. Steps away from ocean water. Bring or rent fishing and snorkel gear nearby to fish right off the dock and enjoy the underwater scenery!

Dec. 1 – 8

$757 CAD 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.

Aug. 7 – 14

$282 CAD per night

Guest favourite

Apartment in Key Largo

4.92 out of 5 average rating, 230 reviews

Waterfront Studio 2| Couples Oasis | Kayaks | Pool

Enjoy gorgeous sunsets and excellent views of Manatee Bay from this beautifully upgraded studio apartment. The perfect spot for couples and small families, this modern studio comes with kayaks and paddle boards so you can get out on the water like a local. The ideal location offers easy access to the Bay, great restaurants, and local beaches. 10 Min Drive to the Gilbert’s Resort 15 Min Drive to John Pennekamp Coral Reef State Park Experience Key Largo With Us & Learn More Below!

Dec. 7 – 14

$302 CAD per night

Guest favourite

Condo in Key West

4.88 out of 5 average rating, 147 reviews

Large waterfront 2/2 end unit with boat slip

Time to fish & relax! Bring your family & friends to this 1350 sqft waterfront corner condo home. Boat slip available on-site with commercial ice machine and fish cleaning station. Located in historic Downtown Key West. Walk/Bike everywhere less 1mi to Duval Street, Seaport, Hemingway House, etc. On-site amenities: heated pool, tiki bar & grills, bike rentals, parking, secure keyless entry, & private elevator. Large park adjacent with tennis courts. 10min from airport (EYW).

Mar. 7 – 14

$1,129 CAD per night

Townhouse in Key West

4.85 out of 5 average rating, 129 reviews

Poolside Cottage #412

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of KW. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and dock. There's also a new bar & grill, Gumbo's, in the resort. When you want to get out and explore KW, you're only minutes from beaches, the seaport and world famous Duval Street! Bikes, golf carts, kayaks, stand-up paddleboards and other watercraft can all be rented locally!

Sep. 8 – 15

$425 CAD per night

Guest favourite

Guesthouse 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.

Oct. 31 – Nov. 7

$310 CAD per night

Apartment in Key West

4.89 out of 5 average rating, 136 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Welcome to our Key West Condo. This spacious well appointed 2 bedroom, 2 bath condo sleeps 6 and is next to the best beach on Key West. This condo is the perfect alternative to staying in a hotel. It gives you a true island experience. Great for Couples and Families We have a Website specific to our Condo where we offer special pricing, discounts and additional pictures Search-keywestbeachsidecondo

Oct. 6 – 13

$853 CAD per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

1357 s f Luxury beachfront resort condo w/ all the amenities - beachfront heated Olympic pool, 3 lighted tennis courts, 20 man hot tub, tropical gardens, beach, saunas, Gym, BBQ Grills everything to make your vacation spectacular! You must be at least 25 years old to rent this property. This is a no animal rental due to extreme allergies of the owner. Thank you for understanding

Sep. 4 – 11

$837 CAD per night

Guest favourite

Houseboat in Key West

4.91 out of 5 average rating, 193 reviews

Key West Luxury Houseboat

EXPANSIVE OCEAN VIEW. 2 Queen Bdrms with Large Ensuite Baths on 1st level. Ocean view 2nd Level Living Room and Full Kitchen with half bath. Spacious fore and aft decks. 15 min from downtown KEY WEST. Located at Stock Island Yacht Club. Panoramic Views from 3rd level sun deck POOL, PRIVATE BEACH, Gym.

Oct. 13 – 20

$1,063 CAD per night

Vacation rentals for every style

Get the amount of space that is right for you.

Cabins

Kick off your hiking boots at these rustic lodgings

Cottages

Quaint homes, peaceful surroundings

Houses

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

Popular amenities for Key West waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Guest favourite

Apartment in Tavernier

4.95 out of 5 average rating, 149 reviews

Boho FL Keys Condo

Mar. 28 – Apr. 4

$658 CAD per night

Guest favourite

Apartment in Key Largo

4.89 out of 5 average rating, 206 reviews

Seaside Vista - Ocean Front 2/1 with dockage

Sep. 14 – 21

$399 CAD per night

Guest favourite

Apartment in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

Nov. 25 – Dec. 2

$484 CAD per night

Guest favourite

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Aug. 22 – 29

$506 CAD per night

Guest favourite

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Oct. 7 – 14

$1,060 CAD per night

Guest favourite

Apartment in Marathon

5.0 out of 5 average rating, 8 reviews

Gated Oceanfront Heated Pool

Jul. 6 – 13

$394 CAD per night

Guest favourite

Apartment in Key Largo

5.0 out of 5 average rating, 21 reviews

Studio apartment in Calusa Resort & Campgrounds

Aug. 21 – 28

$260 CAD per night

Apartment in Key West

5.0 out of 5 average rating, 4 reviews

Partial ocean view studio with king bed

Apr. 12 – 19

$561 CAD per night

Waterfront house rentals

Guest favourite

Home in Marathon

4.99 out of 5 average rating, 107 reviews

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

Aug. 24 – 31

$614 CAD per night

Guest favourite

Home in Key Largo

4.98 out of 5 average rating, 120 reviews

Waterfront Sunsets, Great Price, Relaxing Spot!!!

Aug. 7 – 14

$412 CAD per night

Guest favourite

Home in Cudjoe Key

4.97 out of 5 average rating, 123 reviews

Cudjoe Key Home with a View

Oct. 7 – 14

$561 CAD per night

Guest favourite

Home in Marathon

4.97 out of 5 average rating, 118 reviews

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

Apr. 20 – 27

$989 CAD per night

Home in Key Colony Beach

4.81 out of 5 average rating, 132 reviews

Waterview from three sides, Cabana Club, 30' Docks

Dec. 16 – 23

$590 CAD per night

Guest favourite

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

Feb. 27 – Mar. 6

$575 CAD per night

Guest favourite

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

Aug. 31 – Sep. 7

$1,325 CAD 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

Oct. 6 – 13

$452 CAD per night

Waterfront condo rentals

Guest favourite

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Sep. 18 – 25

$406 CAD per night

Guest favourite

Condo in Key West

4.83 out of 5 average rating, 243 reviews

La Dolce Vita, Old Town Steps to Duval! 3 blks bch

Feb. 7 – 14

$772 CAD per night

Guest favourite

Condo in Key West

4.85 out of 5 average rating, 143 reviews

Anchor Drop modern elegance upgrades throughout vi

Mar. 10 – 17

$1,672 CAD per night

Guest favourite

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Sep. 2 – 9

$666 CAD per night

Guest favourite

Condo in Tavernier

4.93 out of 5 average rating, 134 reviews

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

Dec. 19 – 26

$643 CAD per night

Guest favourite

Condo in Key Largo

4.98 out of 5 average rating, 116 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Aug. 5 – 12

$777 CAD per night

Guest favourite

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

Oct. 24 – 31

$575 CAD per night

Guest favourite

Condo in Key Largo

4.97 out of 5 average rating, 147 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Aug. 7 – 14

$853 CAD per night

Quick stats about waterfront rentals in Key West

Total rentals
310 properties
Rentals with a pool
270 properties have a pool
Pet-friendly rentals
40 properties allow pets
Family-friendly rentals
220 properties are a good fit for families
Total number of reviews
6.2K reviews
Nightly prices starting at
$82 CAD before taxes and fees

Destinations to explore