Key West

We selected the [listingCount] homes worth renting in this location

Book a stay in one of the best homes in [destination]

Entertainment

Bathtub

Hair Dryer

Toiletries

Bathroom

Coffee Maker

Dishwasher

Fridge

Kitchen

Kitchen Utensils

Microwave

Oven

Stove

Kitchen & Dining

Dryer

Extra Pillows and Blankets

Hangers

Iron

Washing Machine

Bedroom & Laundry

Wellness & Fitness

Laptop Friendly Workspace

Wi-fi

Internet & Office

Air Conditioning

Central Heating

Heating & Cooling

Free Parking On Premises

Parking Available

Private Entrance

Parking & Access

Balcony / Patio

Barbeque

Outdoor Seating

Sun Loungers / Beach Chairs

Outdoor

Pets Allowed

Pets

Carbon Monoxide Detector

Child Friendly

Fire Extinguisher

Smoke Detector

Other

Just minutes from the heart of Key West, this home  is a laid-back waterfront escape with room for the whole crew. Five bedrooms, including a playful bunk room, make this home ideal for families and groups, while the open-plan layout keeps everyone connected. There’s a private pool, gated yard, and your own dock outside – perfect for boaters, sun-seekers and four-legged friends alike. With free access to a nearby gym and plenty to see in the local area, it’s  your gateway to easy living in the Keys.

Key Lime Delight

Black-Out Blinds

Heated Pool

Private Pool

Swimming Pool

Beach Essentials

Garden

This home offers an idyllic retreat in Key West. Outside, you can savour blissful days by the heated pool and there's a fire-pit for magical evenings under the stars. Head inside and you'll find the rooms are just as welcoming with plenty of chill-out space and six bedrooms – all of which come with en-suite bathrooms for optimum privacy. Exercise enthusiasts will appreciate the communal gym and if you happen to have a boat you can dock it in the marina. It’s also less than a mile to the heart of Key West and the nearest restaurants. 

The Theodore

Cooking Essentials

Freezer

Toaster

Outdoor Pool

Access to Gym / Spa

Patio / Terrace

Tucked along the water’s edge just minutes from Key West, this breezy four-bedroom retreat blends comfort with coastal charm. With a private heated pool, gated garden, and dock for boats up to 50 feet, it’s made for both downtime and days on the water. The open-plan living space invites long, easy meals or morning coffee with the breeze drifting in. Each bedroom is calm and spacious, with en-suite bathrooms and plenty of natural light. You’ll also find fast Wi-Fi, a washer-dryer, and parking for up to four vehicles. Pet-friendly features and a gym pass are included, and Key West’s best-loved local spots just a short ride—or paddle—away.

Salt and Serenity

Fenced Pool

Just beyond the buzz of Key West, this waterfront villa offers easy-going luxury in a gated community. Outside you can relax in the private pool, fire up the barbecue, or jet off from the private slip. The fenced garden is perfect for kids and pets to roam happily, while complimentary gym access and local dining spots are just minutes away. Whether you’re cruising the Keys or soaking up the sun at home, this spot blends laid-back comfort with everything you need for an unforgettable island escape.

Moonlit Bay

Experience all that Key West has to offer at this waterfront home. It oozes coastal relaxation, from the marina views and swimming pool right down to the private dock. We don't blame you if you'd rather spend all your time in the Florida sunshine, but indoors, there's plenty of space to get together – even with the sofa bed in use, it feels relatively roomy. As for location, you'll be based in a gated community less than a mile from Key West. With access to a nearby gym and the option to arrange boat trips, aquatic adventures, and other experiences, you'll never run out of things to do.

Nautical Nocturne

Ping Pong Table

Fenced Garden

Step off the dock and straight into holiday mode — this waterfront retreat is made for easygoing island days. Set in a gated community with its own private marina, you can moor your boat just steps from the door. Back at the house, there’s a private pool for lazy afternoons, a barbecue for garden grilling, and free access to the estate gym. Inside, it’s all bright spaces and breezy vibes, with a breakfast bar, a big table for family feasts, and a bunk-bed room the kids will love. When adventure calls, local seafood spots and watersports are all within easy reach.

Dream Escape

This modern coastal retreat is all about laid-back luxury and sun-soaked living. With an ultra-sleek design, spacious interiors, and a private pool, it’s made for unwinding in style. Lounge outdoors, gather with friends, or set off on a private boat trip right from your dock. There’s even complementary gym access and a fully equipped kitchen ready for anything from casual dinners to chef-led feasts. You’ll need to climb stairs to access every level, but the comfort, space, and views make it well worth it. Whether you're here to explore or simply relax, this is Keys living at its finest.

 Shellstone Magic

Satellite / Cable TV

Board Games

Library of Books

Sound System

Blender

Ice Machine

Kettle

Rice Maker

Private Washing Machine

Private Dryer

Cleaning Products

Hot Tub

Jacuzzi

Desk

Secured Parking

Private Parking

Gated Community

Self Check-in / Check-out

Smart Home System

Balcony

Fenced Property

Garden Games

Hammock

Outdoor Fireplace / Firepit

Outdoor Kitchen

Outdoor Shower

Rooftop Terrace

Sun Umbrellas

Resort Access

Nice to haves

Waterfront, with its own private dock, landscaped lawns, pool, jacuzzi, ping pong table, and outdoor kitchen, it is all about outdoor living in this sprawling three-storey home. Inside you'll find bright and beachy whitewash interiors, pops of sea blue and natural wood that only accentuate the laid-back lifestyle that comes with the territory. Set in an exclusive gated community, with the best of Key West just a stone's throw away, this homestay is well-suited for group holidays for families and friends.

The New Standard

Welcome home to this stunning 8-bedroom villa in the heart of Lunara Bay, Key West. This luxurious retreat is perfect for families and large groups, offering spacious interiors, a large pool, and lush outdoor areas. Enjoy beautifully designed living spaces, relax by the pool, or explore the nearby attractions. With an exclusive marina for boats up to 40-foot, it's the ideal base for an unforgettable getaway.

 Marina Living

Exercise Equipment

This waterfront home is the perfect spot to bask in the sun, sea, and sand of the Florida Keys. The private boat dock is a highlight, allowing you to explore the vast beaches and reefs of Key West. The private pool is the perfect place to relax during the day, but the open-plan living space is equally inviting, featuring a veranda and alfresco dining area. However, this home isn't just for relaxation – the Peloton, free weights, yoga mats, and gym access mean you can stay active as well. Key Haven is a family-friendly community just a short drive (or boat) from Key West's historic Old Town, where you can explore bustling restaurants and quaint museums. 

Tranquil Bay

Nestled within an exclusive gated community less than a mile from vibrant Key West, this stunning home offers a truly exceptional experience. With breathtaking waterfront views and a private pool, it's the perfect sanctuary to relax and unwind. Designed with impeccable style and generous living spaces, every detail reflects luxury and comfort. With neighbours on either side, it may not be the most remote of stays. But with a private dock slip for boats and secluded areas in the garden, it's the ideal retreat for those seeking a luxurious getaway with a touch of exclusivity.

Waterfront Pearl

Discover the magic of Florida from this impressive home in Key West. Outside, you can relax and unwind by the private heated pool. There’s a family-friendly yard and a fire pit for magical evenings under the stars. Inside, the rooms are just as inviting with plenty of space to socialise and stretch out across the six bedrooms. Guests can enjoy access to the communal gym and there’s a dock for boats. Plus, your host can help organise a range of extra services – including tailored experiences and chauffeurs. And when it comes to explorations further afield, you'll find all the attractions of Key West within easy reach – including restaurants and bars.

Paradise Key

High Chair

This home has bagged itself a great location in a gated community, less than a mile from ever-popular Key West. With a private pool, alfresco dining area, and fire pit, outdoor living is easy here. Keen sailors can bring their boat and dock it at the on-site marina, and there’s plenty of room in the driveway for your boat trailer. If you’re feeling active, check out the gym at the nearby fitness centre. Or if you want a more relaxing experience, your host can arrange a private chef to cook for you in the home. We think this place is a great option for those wanting to experience Florida Keys with a touch of luxury.

Marina Nights

This impeccably decorated home is a masterclass in island elegance, where every detail has been thoughtfully designed for comfort and style. It's light-filled, spacious, and beautifully finished with a refined, coastal touch. Set just minutes from vibrant Key West, you’ll have the best of the island at your fingertips. There's even access to a private marina slip at an exclusive marina, perfect for unforgettable days on the water. At full occupancy, six guests will share one room with two bunk beds, making it especially well-suited for families with children. You’ll need to climb stairs to reach all areas of the home, but with so much space and beauty throughout, it’s more than worth it. A true sanctuary for those seeking luxury, warmth, and adventure.

Island Sophisticate

Wine Cooler

Stair Gates

If you’ve ever dreamed of a tropical getaway in the sun, with palm trees swaying and crystal blue waters visible from the kitchen window, this is the place for you. Located in the iconic Key West, this five-bedroom home offers every comfort you’d expect from a Floridian home right on the water – including a fenced pool, a spacious and fully-equipped kitchen, and even your own private dock extending into the sea. With complimentary gym access, keyless entry and plenty of room to relax, this remarkable home is a true gem in the Florida Keys.

Key Sunset

Spend your days soaking up the island breeze at this laid-back retreat just outside Key West. Tucked inside a quiet gated community, this spacious six-bedroom home is made for group getaways, with a private boat slip, breezy balconies, and enough room for everyone to spread out. The vibrant streets of Old Town are just a few minutes away by car, bike, or golf cart if you're feeling adventurous. Or, you can take it easy, dipping in the pool, or firing up the grill for a sunset dinner. Thoughtful touches like free gym access makes island life feel like a home-from-home.

The Pearl of Key West

This spacious and stylish waterfront home offers the perfect setting for a relaxing Key West getaway. The bright, open-concept layout is ideal for family gatherings or entertaining friends. Dine in with loved ones, enjoy a poolside BBQ, or head out to savour fresh seafood at nearby restaurants. To explore the local area, rent a golf cart, scooter, or bike, or take to the waters with a boat or kayak. After a day of adventure, return to unwind on your balcony with stunning waterfront views, or relax in your private pool.

Key West Retreat

Set beside the water in a quiet gated community, this Key West retreat is all breezy days and golden-hour swims. Coastal tones and soft natural light bring a sense of calm throughout, while outside, the private pool, dock, and fenced garden make it easy to unwind. Start your mornings with coffee on the terrace, then take to the water or stretch out with a yoga mat in the sun. Inside, the open-plan living space is perfect for lazy lunches, slow dinners, and long conversations. There’s a Peloton for active days, high-speed Wi-Fi for staying connected, and parking for four vehicles. A gym pass is included, and with beaches, boat ramps and island favourites close by, the best of the Keys is within easy reach.

The Tidal Flow

Tucked along the water’s edge in a peaceful gated community, this four-bedroom Key West retreat is made for laid-back days and warm, breezy nights. With a private heated pool, a gated garden, and a dock for boats up to 50 feet, it’s an ideal home for family and friend getaways. The open-plan kitchen and dining area are perfect for slow meals or morning coffee with the doors open wide. You’ll find two king bedrooms, four twin beds, a queen sleeper sofa, and plenty of space to relax inside or out. There’s high-speed Wi-Fi, a washer-dryer, and parking for up to four vehicles. A gym pass is included, and Key West’s beaches, boat ramps, and hidden gems are all close by.

Dockside Dreams

First Aid Kit

If you’re seeking an authentic Florida Keys experience, then look no further. This home is located within a gated community, less than a mile from popular Key West. With a private pool, fire pit, and choice of terraces to enjoy, this place is designed with relaxation in mind. And if you’re bringing the boat, there’s a spot saved for you at the marina, just moments from the front door. When you’re not firing up the barbecue for a flame-grilled feast, your host can arrange a private chef to cook for you. And gym bunnies can work out for free, at the nearby fitness centre. 

Keys to Paradise

This waterfront house is in a great spot, tucked away in a gated community, less than a mile from popular Key West. Perfect for families or groups, the home centres around the open-plan living area, which makes entertaining a breeze. Outside you’ve got a private pool to enjoy, a terrace for alfresco dining, and a private dock if you’re bringing the boat. While it’s a plus that all the bedrooms are en-suite, it’s worth noting that at full capacity, when two guests will be sleeping on a sofa bed in the living area, they’ll only be able to access a shower through one of the bedrooms. There is a separate toilet though, so this needn’t be a deal-breaker.

Sunset Key

Ironing Board

Ceiling Fans

The perfect beach holiday spot. Located just a 1 min walk from the beach and the Intracoastal Waterway, this cozy one-bedroom apartment is nestled in the heart of Fort Lauderdale's Central Beach. Experience beach living at its finest with Seaside Serenity. Immerse yourself in its inviting atmosphere, where relaxation and tranquility come naturally. Savor serene nights in lighter-than-cotton bedsheets, indulge in bath rituals with natural Pure Fiji products, and wrap yourself in opulent towels. The shared lush backyard patio boasts an outdoor dining and grilling area – a perfect place to unwind and share a meal. Discover Coastal Bliss as you explore the vibrant local area, with its array of restaurants, bars, shops, and entertainment options just steps away from your doorstep. Seize the essence of seaside living with a stay at Seaside Serenity.

Sandcastle Retreat

Pool / Snooker Table

Shared Pool

This stunning residence boasts nine bedrooms split into three suites, each with their own private entrance, making it perfect for multiple families or large groups. Nestled right on the waterfront, the property offers spectacular panoramic views and direct access to a private dock. The two most outstanding features are the heated pool and the al fresco dining area, both of which invite guests to savor the delightful coastal breeze and bask in the warm sunshine. Impeccably furnished and tastefully decorated, each suite offers spacious living areas, fully equipped kitchens, and comfortable bedrooms with Smart TVs. Additionally, guests can enjoy complimentary access to beach gear and kayaks. With its ideal location just moments from the beach and a short drive to local attractions, this breathtaking retreat promises an unforgettable vacation for all who visit.

Lakeside Getaway

Smart TV

Games Room

Shared Washing Machine

Shared Dryer

Tennis Court

Bicycles

Parking On Premises

Lift Access

Free Parking On Street

Paid Parking On Premises

Paid Parking On Street

Access to Beach

In the very heart of Palm Beach, this comfortable apartment is ideal for exploring on foot. Just a short walk away you'll find delicious restaurants, shops, and a sandy beach. It's part of a historic aparthotel, so you'll also have access to shared on-site amenities – from a heated pool and covered veranda outdoors to a salon and spa offering manicures inside. The pad itself is small but cosy. There are a few quirks to be aware of here, including a coin-operated laundry room, a small plug-in hotplate instead of a hob, and a sofa bed for guests three and four. All worth it for the coastal location, though.

Sunlit Hideaway

Piano

Pod Coffee Machine

Fireplace

Welcome Hamper

It’s hard to know where to begin when describing this 1920s estate, there are so many incredible details. The main house is a grand, Spanish-style villa housing four bedrooms. A covered walkway leads to the studio space – pause for a moment and admire the orchids as you go. If you fancy learning a new skill, perhaps flower arranging or shibori, your host can arrange for workshops to take place in the studio (which can also be set up as a lavish 7th bedroom). Two one-bed apartments can be found in the garden, giving additional guests a bit of privacy. The half-acre of grounds was designed for outdoor living, whether you’re grilling up dinner on the BBQ, wandering amongst the palms or settling on the shaded outdoor sofa. Temperature-wise, the brilliant white stone walls keep things cool inside. Style-wise, the boho-chic furniture has the same effect. We don’t blame you if you never set foot outside the gates, but if you’d like to do some sightseeing then the city of West Palm Beach area has plenty to keep you occupied, from art galleries to water parks.

Orchid White

Security Cameras

There’s so much to love about this Floridian home. With plenty of space for everyone to spread out, it’s easy to spend time with loved ones or find a private corner for some quiet time here. The outdoor space makes the most of the tropical climate, and with a pool, hot tub, plenty of seating and opportunities for alfresco dining, outdoor living is a breeze. Fancy a beach day? Hire a golf cart and whizz to the coast in just two minutes, or if you fancy a stroll in the sunshine, it’s a mere ten-minute walk. 

Sunsets in the Fort

Baby Monitor

Cot / Crib

Drying Rack

Sauna

Single-Level Home

Safe

Lying just outside of the sunny city of Naples on Florida’s west coast, this sprawling villa has plenty to offer for those looking for a relaxing getaway. Whether it’s the pickleball court, private gym or half basketball court beckoning you in, or the enticing pool or sauna catching your eye, this house has something for everyone. While there is bed space for more than sixteen guests, you’ll need to get permission from your host to add more than this. When you’re ready to see the sights, hop in your car and explore the Naples Pier, an especially pretty sight at sunset.

Floridian Retreat

EV Charger

Kids and pets will appreciate the large outdoor space at this two-bed home in Fort Lauderdale – perfect for water fights, playing catch or just lying in the hot tub beneath the lush, shady trees. There’s also a heated pool for an invigorating early morning swim. What’s more, it is completely private – you won’t be sharing anything with anyone. An open-plan kitchen and living space with an island makes for sociable dinner prep, though there’s also a home office if you need an escape. The surrounding South Middle River neighbourhood is a quiet suburban spot, popular with families and dog-walkers.

Six Leaves Left

Playground

Free Parking

This stunning 2 side-by-side homes on the lake offer guests plenty of space to soak up the sun, with a total of 2,940 square feet of luxury living. The open-plan living room is perfect for spending quality time with friends and family, and the bedrooms are all outfitted with fresh linens, plump pillows, and ultra-comfy mattresses. The lake is right in your backyard, so you can jump into a kayak and explore the serene landscapes around you. There's also a pool, a hot tub, a hammock, and a massive outdoor dining table.

Views In The Making

Workplace

Floor-to-ceiling windows mean that you don’t even have to try to tear your eyes away from the water view here. This home sits on the edge of Harbor Inlet, looking out over the Port Everglades waterway. From your deck, heated pool, or elegant open-plan dining and living space, you can admire yachts as they cruise by. You’ll even have access to a private beach, which appears at low tide. Kids will love the games room, while grown-ups will enjoy sipping chilled drinks around the fire pit.

Dream of the Open Sea

Amazon Prime

Netflix

Home Cinema Setup

Sonos

Streaming Services

Luxury Toiletries

Rain Shower

Espresso Machine

Laundry Supplies

Luxury Bedding

Vacuum Cleaner

Electricity Adaptors

Printer

Temperature Control

Not short on outdoor seating, this beautiful house embraces the tropical atmosphere of south Florida. The signature palm trees and meticulous landscape design surround the swimming pool creating an enchanting private oasis. Prepare for all your outdoor needs to be met – from a convenient grill to a table for alfresco dining. Apart from spacious bedrooms, you'll find an office and a second living area doubling as a fourth bedroom. Although having only two bathrooms for eight guests might require some coordination, this home's exceptional surroundings, convenient location and high-end furnishing will sweep you off your feet.

Blue Water & Palm Trees

Book a stay in one of the best homes in Key West

We selected the 282 homes worth renting in this location

Who's coming along?

Home spotlights in Key West

We selected the top 3% holiday homes in Key West

Most popular homes in Key West

Check upcoming rates & availability for Key West

Frequently asked questions