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Waterfront vacation rentals in Key West

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Top-rated waterfront rentals in Key West

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

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Vacation 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.

Jul 18 – 25

G$38,128 GYD per night

Apartment in Key Largo

4.94 out of 5 average rating, 248 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!

Oct 28 – Nov 4

G$37,013 GYD per night

Houseboat in Key West

4.81 out of 5 average rating, 254 reviews

Key West Houseboat Paradise

56 foot houseboat (1987), Fully Rebuilt in 2022. On a old 15 slip dock on Stock Island, 15 min drive to Key West. Big living room, Full Kitchen, Queen Bdrm + sofa bed. The dock is very local, 'old Key West' sort of vibe with mostly older live-aboard boats. The property has an fairly industrial feel to it with a 2-bay local garage/taxi company on site so Shore Side is nuthin' fancy but the back deck looks out on mangrove islands dotting Boca Chica Channel with two 12' Sea Kayaks ready to go.

Mar 9 – 16

G$80,298 GYD per night

Vacation 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

Sep 19 – 26

G$42,226 GYD 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.

Sep 3 – 10

G$36,308 GYD per night

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.

Oct 24 – 31

G$39,052 GYD per night

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).

Apr 14 – 21

G$148,794 GYD per night

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.

Oct 29 – Nov 5

G$71,377 GYD per night

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.

Aug 24 – 31

G$85,014 GYD per night

Condo in Key Colony Beach

4.91 out of 5 average rating, 112 reviews

Beachside Unit 39 Tiki Huts, Private Beach & Pool

Unit 39 Details: Second Floor Unit, Tub with Shower, Two Queen Beds, Maximum Occupancy 4 Guests, No elevator on site and Not Handicapped Accessible. A registration and liability waiver form signature will be required as part of your reservation. Our oceanfront property includes a private heated pool and private beach retreat on the Atlantic Ocean. Welcome to Continental Inn Condominiums in Key Colony Beach, Florida known as “The gem of the Florida Keys.”

Aug 22 – 29

G$48,562 GYD per night

Townhouse in Key West

4.91 out of 5 average rating, 109 reviews

Poolside Cottage #411

Welcome! This beautiful cottage is located in the Coconut Mallory Resort & Marina on the eastern end of Key West. This secluded, waterfront oasis includes outdoor pools, hot tub, on-site marina and boat 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, kayaks, paddle boards and golf carts can be rented locally

Sep 12 – 19

G$58,763 GYD per night

Guesthouse in Key Largo

4.91 out of 5 average rating, 191 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 5 – 12

G$42,302 GYD per night

Vacation rentals for every style

Get the amount of space that is right for you

Cottages

Quaint homes, peaceful surroundings

Villas

Luxurious estates for the ultimate escape

Bungalows

Intimate homes. inviting architecture

Popular amenities for Key West waterfront rentals

Free parking on premises

Air conditioning

Waterfront apartment rentals

Apartment in Key West

4.89 out of 5 average rating, 135 reviews

Key West Beachside 1400sf, 2 Bedroom Condo

Mar 7 – 14

G$157,592 GYD per night

Apartment in Key West

4.92 out of 5 average rating, 175 reviews

KW Luxury 2/2 Beachfront resort Tropical Oasis

Jan 31 – Feb 7

G$145,159 GYD per night

Apartment in Tavernier

4.95 out of 5 average rating, 147 reviews

Boho FL Keys Condo

Oct 22 – 29

G$61,392 GYD per night

Apartment in Key Largo

4.98 out of 5 average rating, 125 reviews

Key Largo Kawama Lagoon Free Cancel Deutsch Spain

Sep 3 – 10

G$65,017 GYD per night

Apartment in Key Largo

4.92 out of 5 average rating, 106 reviews

2/1 Oceanfront Apartment with Dockage

Apr 10 – 17

G$76,541 GYD per night

Apartment in Tavernier

4.83 out of 5 average rating, 255 reviews

Breathtaking Oceanfront Views at Tropical Daze

Apr 3 – 10

G$62,254 GYD per night

Apartment in Key West

4.94 out of 5 average rating, 16 reviews

Oceanfront Condo in Key West

Aug 29 – Sep 5

G$145,388 GYD per night

Apartment in Key West

5.0 out of 5 average rating, 3 reviews

Partial ocean view studio with king bed

Apr 12 – 19

G$76,826 GYD per night

Waterfront house rentals

Home in Key Colony Beach

4.96 out of 5 average rating, 134 reviews

Beautiful open plan remodeled home in Key Colony

Oct 23 – 30

G$43,660 GYD per night

Home in Marathon

4.97 out of 5 average rating, 117 reviews

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

May 22 – 29

G$118,311 GYD per night

Home in Cudjoe Key

4.97 out of 5 average rating, 121 reviews

Cudjoe Key Home with a View

Oct 7 – 14

G$75,986 GYD per night

Home in Key Largo

5.0 out of 5 average rating, 50 reviews

The Paradise 2

Mar 20 – 27

G$80,875 GYD per night

Home in Upper Sugarloaf Key

4.87 out of 5 average rating, 45 reviews

Bungalows at Sugarloaf Beach - The Lighthouse

Feb 5 – 12

G$192,900 GYD per night

Home in Marathon

5.0 out of 5 average rating, 16 reviews

Horizon

Aug 31 – Sep 7

G$168,346 GYD per night

Home in Cudjoe Key

4.86 out of 5 average rating, 42 reviews

*Emerald Seas*-Florida Keys Ocean Front Paradise!

Oct 10 – 17

G$101,978 GYD per night

Home in Key Colony Beach

4.98 out of 5 average rating, 51 reviews

Captain’s Quarters Ahoy Mateys! Florida, Keys

Apr 15 – 22

G$56,827 GYD per night

Waterfront condo rentals

Condo in Tavernier

4.95 out of 5 average rating, 108 reviews

Key Largo Coastal Condo-Ocean View ~ Pool ~ Beach

Aug 30 – Sep 6

G$56,418 GYD per night

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 16 – 23

G$105,470 GYD per night

Condo in Tavernier

4.98 out of 5 average rating, 142 reviews

Ocean Views at Ocean Pointe

May 31 – Jun 7

G$43,463 GYD per night

Condo in Tavernier

4.96 out of 5 average rating, 159 reviews

Best View Ocean Pointe Pool Beach King Bed, Gated

Sep 29 – Oct 6

G$87,267 GYD per night

Condo in Tavernier

4.93 out of 5 average rating, 133 reviews

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

Jan 24 – 31

G$79,592 GYD per night

Condo in Key Largo

4.98 out of 5 average rating, 115 reviews

Oceanfront Condo w/Lake, Kayak, Paddleboard & Bike

Nov 7 – 14

G$101,913 GYD per night

Condo in Tavernier

4.8 out of 5 average rating, 130 reviews

TROPICAL PARADISE Ocean Condo - Cabana Daydreamin'

Nov 14 – 21

G$49,985 GYD per night

Condo in Key Largo

4.97 out of 5 average rating, 146 reviews

KEYS BEACH RETREAT WITH CAPTIVATING WATERVIEW!

Nov 13 – 20

G$140,953 GYD 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
G$12,538 GYD before taxes and fees

Destinations to explore