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

Black-Out Blinds

Dryer

Extra Pillows and Blankets

Hangers

Iron

Washing Machine

Bedroom & Laundry

Heated Pool

Private Pool

Swimming Pool

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

Beach Essentials

Garden

Outdoor

Pets Allowed

Pets

Carbon Monoxide Detector

Fire Extinguisher

Smoke Detector

Other

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

Fenced Garden

Outdoor Fireplace / Firepit

Outdoor Seating

Patio / Terrace

Sun Loungers / Beach Chairs

Sun Umbrellas

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

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

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

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

Freezer

Wine Cooler

Self Check-in / Check-out

Fenced Pool

Fenced Property

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

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

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

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

Toaster

Outdoor Pool

Access to Gym / Spa

Child Friendly

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

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

Ping Pong Table

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

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

Smart Home System

Balcony

Garden Games

Hammock

Outdoor Kitchen

Outdoor Shower

Rooftop Terrace

Resort Access

Nice to haves

Set in an exclusive gated community, with the best of Key West just a stone's throw away, this homestay is well-suited for families and friends. Needless to say, outdoor living was the key priority when designing this sprawling three-storey home. The property is waterfront with its own private dock, pool, Jacuzzi, ping pong table, and outdoor kitchen. Inside, you'll find beachy whitewash interiors and natural materials that only accentuate the laid-back lifestyle, and with your very own Guest Experience Manager to help co-create the trip of your dreams, we have no doubt a stay here will be beyond memorable.

The New Standard

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

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

Cooking Essentials

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

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 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

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

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

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

Smart TV

Ironing Board

Printer

Workplace

Fireplace

Parking On Premises

EV Charger

Beach / Pool Towels

Safe

You’ll find this modern, adult-only home in Old Naples, a short walk from Fifth Avenue with its plethora of delicious eateries and trendy shops. Comfortable for eight, each bedroom boasts an ensuite and with two separate living areas, there’s plenty of room for guests to spread out here. The outdoor space, however, is sure to be a hit and where everyone naturally congregates. Sun-kissed terraces, alfresco dining and a private pool – what’s not to love? Locally, it’s a mere eleven-minute stroll to Naples beach – perfect for soaking up the sun from the sea or sand. 

Naples Aglow

Games Room

Pool / Snooker Table

Ceiling Fans

Get a taste of coastal living in this Florida holiday pad, just a minute’s stroll from the golden sands of Fort Lauderdale Beach. When you’re not at the beach, you can relax among the tropical plants in the garden, enjoy a barbecue on the terrace or take a dip in the private pool. Kids and teens will love the games room, with its multi-use pool and ping pong table, and for a relaxing spa experience, the main bedroom boasts a Jacuzzi bathtub. Within walking distance of the home, you’ll also find a variety of restaurants and peaceful Birch State Park.

Endless Ocean

Piano

Pod Coffee Machine

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

Shared Washing Machine

Shared Dryer

Shared Pool

Tennis Court

Bicycles

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

Free Parking

Single-Level Home

Only a stone’s throw away from the Intracoastal Waterway and Currie Park, this Florida home spreads its four bedrooms across the main house and guest house, connecting the two with a tropical outdoor space that echoes the surroundings. 

Spend days out basking in the sun as you go from sun lounger to private pool and back again. Bookworms will especially enjoy reading in the shade of the palms or at the edge of the pool where legs can dangle into the cool water. 

The enclosed porch is the perfect segue between the outdoors and indoors, and groups can enjoy the space with ice-cold drinks and games of charades, but not before a day out exploring Palm Beach. 

Hit the beach, visit the Mediterranean market minutes from your door, and dine at any of the surrounding restaurants and cafes. Golfers can find their escape to Palm Beach Country Club at the other end of a short drive or by visiting The Ocean Course at The Breakers, Lake Worth Beach Golf Club or the Drive Shack. 

Palm to Palm

Perched right on the canal, this waterfront home is just a stone's throw from the best of Fort Lauderdale. Whether you're sprawled out on Lauderdale-by-the-Sea Beach (3 miles away), wining and dining at the nearby eateries, or enjoying a lazy afternoon on the terrace, this home offers something for everyone. The swimming pool is sure to be a hit, and there's a private dock if you're in the mood to cruise down the canal. Inside, the living space boasts a sofa bed for two guests, a pool table, and a cosy atmosphere. Having only two bathrooms isn't ideal, but that aside, this is a comfortable option for fun in the Fort Lauderdale sun.

Sunshine Sweets

Foosball / Table Football

Baby Bath

Cot / Crib

This modern yet homely apartment is perfectly situated just footsteps from Hollywood Beach. Inside, a cool neutral colour scheme creates a casual yet elegant atmosphere. Spend unhurried mornings lounging in the living space as the appointed chef of your group cooks up a storm in the fully-equipped kitchen. After a hearty breakfast, steal a moment for yourself on the balcony – get stuck into a good book from your host's collection as a breeze ripples through the palm trees. 

When you fancy a change of scenery, check out your building’s amenities – you’ll find a gym, shared office space and a clubhouse. Outside, a communal pool is the tonic to hot and humid Florida summers. If you’re keen to explore further afield, check out Aventura Mall before filling up on seafood at a nearby waterfront restaurant. 

Bergamot & Sunshine

Located in the residential area of Victoria Park in Fort Lauderdale, this convenient spot offers the ideal set-up to those seeking a holiday by the beach not far from Miami. With plenty of workspaces and high-speed wi-fi here, it also suits those in town on workcations. Meanwhile, the heated swimming pool and barbecue are sure to come in handy if you're keen to spend lazy days in the sun. Here, the home's luxury finishing touches set it apart – expect high thread count linens, luxury toiletries and Nespresso coffee machines. It's worth bearing in mind that when this home is booked at full occupancy, two guests will be sleeping on the queen-sized pull-out bed in the living area.

Rockpool

Netflix

Desk / Workplace

Multiple Sets of Keys

Throws

Utterly Instagrammable, this delightfully designed studio space offers you the perfect getaway in West Palm Beach. The layout is open plan, in a warehouse-style space that looks modern on the inside and Mediterranean on the outside. High ceilings, white-painted walls, stone floors and minimal furniture create a fresh and bright feel, perfect for long-sunny days. Every element of this home feels both elegant and personal, and there are plenty of different areas for sitting and relaxing. We especially loved the bed, which celebrates Islamic design and feels fit for a sultan. This royal-feel is carried into the outside, where there is an ornate water fountain and gorgeous courtyards. You will also find an orchid garden and two custom cedar picnic tables, where you can dine alfresco with other guests. Though this space feels secluded, it's right in the heart of West Palm Beach and a two-minute drive or ten-minute walk to West Palm Beach Golf Course. If you fancy a day on the area's gorgeous sands, a number of beaches, such as Boynton Beach, are around a ten-minute ride away.

The Sultan

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

Baby Monitor

Drying Rack

Sauna

Security Cameras

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

Umbrellas

This state-of-the-art apartment offers a refreshingly modern aesthetic right on the oceanfront. Spend serene mornings out on the private balcony soaking up an infinity of blue over your morning coffee. 

The laid-back, contemporary vibe of the apartment is most definitely in keeping with the beachside lifestyle, where you're encouraged to kick back and relax to the sound of the waves lapping into the shore. Floor-to-ceiling windows welcome floods of natural daylight and the fresh ocean breeze to flow through the space in harmony. 

Walk down to the beach and feel the sand between your toes, or enjoy the shared pool, hot tub and gym facilities accessible to resort guests only. Here you'll have leisure at your fingertips as there are also on-site dining options, a spa, a hairdressing salon and a concierge desk that can help you with any special requests and additional luxury services. 




Chasing the Waves 

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

We selected the 540 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