I’ve visited Key West five times, and let me tell you—staying in the right rental completely transforms the experience! Nothing beats waking up to ocean views or sipping morning coffee on a historic home’s porch just steps from all the action.
After exploring countless options, I found the sweet spots: Old Town near Mallory Square with its perfect blend of charm and convenience, and Truman Annex with its quieter, upscale vibe and gorgeous landscaping. These are truly the best places in Key West to feel like a local while still enjoying all the sunshine, fresh seafood, and those famous sunset celebrations that make this island so special. From cute cottages to luxurious waterfront homes, these 13 vacation rentals will make your Florida Keys getaway absolutely unforgettable!
Vacation Rentals in Key West: Top Stays in Key West, FL
Here are the best vacation rentals in Key West, FL, by category, considering factors including amenities, trip types, and budgets. The subsequent sections will cover each listing in more detail.
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- Perfect Rental for Pool Activities: Located in Old Town Key West
- Awesome Rental for Peace and Quiet: Offers Total Pivacy for Guests
- Top Stay for Architecture Enthusiasts: Combines Old and New Designs
- Best Vacation Spot for Romantics: Rental Meant to Accommodate 2 Guests
- Elite Rental for Those Seeking Amenities: Award-Winning Master Suite
- Great Vacation Rental for Luxury Living: Located Near Duval Street
- Best Rental for Travelers with Pets: Access to Attractions, Private Amenities
- Top Vacation Home for History Buffs: Features Pristine Poolside Layout
- Best Rental in a Community Atmosphere: Recently Renovated Interior
- Top Option for City Living: Located in the Truman Annex Neighborhood
- Elite Rental for Nature Lovers: Surrounded by Tropical, Floral Scenery
- Great Vacation Rental for Chilling Out: Comes with a Long List of Amenities
- Cozy Rental with a Private Pool: Distinct Unit with a Unique Structural Flare
13 Vacation Rentals in Key West: Top Vacation Homes in FL
Finding a beautiful vacation rental surrounded by beaches and island landscapes has never been so simple! With our list of the 13 best vacation rentals in Key West, you’ll be treated to fun activities, luxurious amenities, and the best the tropical life has to offer. Check out all 13 options below!
1. Mango Margarita Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $962/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Heated private pool, outdoor deck, off-street parking
- 🌟 Perfect For: Relaxation seekers 🌴, family getaways 🏖️, adventure lovers 🌞
Escape to Mango Margarita, a tropical retreat in the heart of Key West! This 1416 sq. ft. home features 2 spacious bedrooms with king-sized beds and en suite bathrooms, plus a queen sofa sleeper in the living room, accommodating up to 6 guests.
Cook in the fully stocked kitchen or enjoy meals at the dining table for 6. Relax in the cozy living room with a flat-screen TV or unwind outside by the private heated pool, surrounded by a large outdoor deck perfect for dining or lounging in the sun.
Located just a block from Duval Street, you’re a short walk to South Beach, Southernmost Point, and just minutes from top attractions. Perfect for those seeking a mix of relaxation and adventure, Mango Margarita offers the ideal escape in Key West!
2. Luxury High-End Condo
- 📍 Location: Key West, FL
- 💵 Price Per Night: $342/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Ocean-view balcony, private beach access, high-speed Wi-Fi, two bikes
- 🌟 Perfect For: Couples 👫, digital nomads 💻, beach lovers 🏝️
Unwind in this luxury beachfront condo in the heart of Key West. With resort-style amenities and thoughtful touches, this stylish retreat offers the perfect blend of comfort and convenience.
Inside, the open living area features a dedicated workstation and plenty of natural light. The fully equipped kitchen, king bedroom, and twin Murphy bed make it easy to relax, work, or entertain. Step onto the balcony to sip your morning coffee from comfy chairs with a peek of the ocean.
Enjoy access to a private natural beach, sparkling pool, hot tub, and fitness center. Two included bikes make exploring local hotspots like Duval Street and Smathers Beach a breeze.
From ocean adventures to quiet evenings by the pool, this condo is your perfect base in paradise.
3. The Blue Bungalow Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $466/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Community pool, outdoor dining area, electric grill
- 🌟 Perfect For: Family getaways 🏖️, adventure lovers 🌞, relaxation seekers 🌴
Relax at Blue Bungalow, a charming tropical retreat in the heart of Key West! This 960 sq. ft. townhome features 2 cozy bedrooms with a king-sized bed in the master and a queen bed in the second, accommodating up to 6 guests.
Cook in the fully stocked kitchen or enjoy meals at the dining table for 4. Relax in the cozy living room or step outside to unwind in the covered outdoor space with dining for 6 and an electric grill.
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Located just a short walk from Duval Street, you’re close to key attractions like the Ernest Hemingway Home and Museum, Mallory Square for sunset views, and Ft. Zachary Taylor Historic State Park for beach access and historic tours.
Ideal for those seeking both relaxation and adventure, Blue Bungalow is the perfect getaway in Key West!
4. Old Town Bali Hideaway
- 📍 Location: Key West, FL
- 💵 Price Per Night: $360/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Tropical thatched ceiling, private gated courtyard, European-style kitchen
- 🌟 Perfect For: Couples 💑, solo travelers 🌴, island explorers 🚶♂️
Welcome to the Old Town Bali Hideaway – a cozy studio retreat tucked in the heart of Key West, just a short stroll from the energy of Duval Street. This tropical-inspired escape is perfect for two, offering a peaceful home base in a vibrant island setting.
Indoor, the studio features a queen bed, a thatched ceiling, cool tile floors, and a fully equipped European-style kitchen. French doors open to a private gated courtyard, creating a seamless indoor-outdoor living space.
Unwind in the shade, take a dip in the shared pool, or walk to Mallory Square for sunsets and live music. With top attractions like the Hemingway Home and local beaches nearby, you’re never far from your next adventure.
From morning coffee in the garden to lively evenings in Old Town, this Bali-inspired hideaway brings the best of Key West right to your doorstep.
5. Pineapple Cottage Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $864/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Private pool, outdoor dining, BBQ grill, steps from Duval Street
- 🌟 Perfect For: Couples 👫, relaxation seekers 🌴, small families 👨👩👧👦
Pineapple Cottage is a charming 2-bedroom, 2-bathroom home located just half a block from Duval Street in Old Town Key West. This tropical retreat offers a private pool, a charcoal grill, and comfortable seating surrounded by lush landscaping.
Throughout, the open living space includes a fully equipped kitchen and a cozy living room with a sofa and entertainment options like cable TV and a sound system. The kitchen is fully stocked and features a breakfast bar with seating for two.
Nearby, stroll along Duval Street for restaurants, or visit the Ernest Hemingway Home and Museum to explore. Take a short walk to Mallory Square for street performances.
Whether you’re shopping, sightseeing, or enjoying the sunset, this location offers endless charm and adventure.
6. Cozy Conch Cottage
- 📍 Location: Key West, FL
- 💵 Price Per Night: $381/night
- 🛏️ Sleeps: 2 guests
- 🔥 Unique Features: Private hot tub, tropical patio, outdoor shower, pet-friendly
- 🌟 Perfect For: Couples 💑, island adventurers 🚲, pet lovers 🐾
Step into Conch Cottage, a charming Old Town hideaway just steps from the best of Key West. This one-bedroom retreat offers laid-back island vibes and thoughtful amenities for a relaxed and memorable stay.
Within, you’ll find a bright and airy living space with an open-concept kitchen, dining, and lounge area. The queen bedroom offers a cozy spot to recharge, while the private outdoor patio features lush landscaping and a hot tub for unwinding after a day of exploring.
Rinse off under the outdoor shower, sip cocktails in the tropical courtyard, or walk to nearby favorites like the Hemingway Home, Mallory Square, and Duval Street’s restaurants and nightlife.
From sunny beach days to romantic evenings under the stars, Conch Cottage is your perfect home base in the heart of Key West.
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7. Dancing Palms Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $328/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Private hot tub, community pool, covered carport, steps to Duval Street
- 🌟 Perfect For: Couples 👫, small families 👨👩👧👦, relaxation seekers 🌴
Dancing Palms is a bright 2-bedroom, 2-bathroom townhome located in the prestigious Truman Annex, just 2 blocks from Duval Street. This prime location puts you within walking distance of iconic attractions like the Truman Little White House, Mallory Square, and Fort Zachary Beach State Park.
The open-plan first floor features a fully equipped kitchen, dining area, living space, and a full bathroom. Upstairs, the master bedroom offers a king bed, private balcony, and en-suite bathroom. The second bedroom has two twin beds that can be converted to a king.
Enjoy modern amenities, including flat-screen TVs in each room, a washer/dryer, and complimentary Wi-Fi. After a day of exploring Key West, unwind in the private hot tub or take a refreshing swim in the President’s Row community pool.
8. Captain’s Choice Condo
- 📍 Location: Key West, FL
- 💵 Price Per Night: $368/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Private balcony, shared pool, hot tub, free parking, washer/dryer
- 🌟 Perfect For: Relaxation seekers 🌅, beach lovers 🏖️, family getaways 👨👩👧👦
Unwind at Captains Choice, a fully renovated 2-bedroom, 2-bathroom condo at Sunrise Suites Resort in Key West. This modern retreat features a private balcony with breathtaking views of the salt ponds and sunset.
The condo offers top amenities, including a heated pool, hot tub, gym, and tennis court. It’s just 3 minutes from Key West International Airport (EYW), making it convenient for travelers.
Nearby, relax at Smathers Beach or enjoy a round at Key West Golf Club. Take a short drive to Duval Street for shopping and dining. Whether you’re golfing, beachcombing, or exploring the vibrant island, this location offers the perfect blend of adventure and relaxation.
9. Private Family Retreat Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $350/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Private deck, full kitchen, pet-friendly, steps from Duval Street
- 🌟 Perfect For: Couples 💑, small groups 🌴, Key West explorers 🚶♀️
Settle into Kate’s Krawl – a private Old Town retreat just a minute’s walk from the lively heart of Duval Street. This cozy one-bedroom home offers comfort, charm, and an unbeatable location for your island escape.
Inside the home, you’ll find a king bedroom, a full bath, and an open living area with a sleeper sofa to accommodate up to four guests. The well-equipped kitchen, bar-top dining, and inviting lounge area make it easy to settle in and relax.
Step outside to your outdoor deck—perfect for morning coffee, evening drinks, or a casual cookout on the grill. Traveling with pets? This home is pet-friendly, too.
Just steps away, stroll Duval Street, visit the Ernest Hemingway Home and Museum, or snap a photo at the iconic Southernmost Point. Kate’s Krawl puts you right in the heart of Key West adventure.
10. Chick-A-Pea Cottage
- 📍 Location: Key West, FL
- 💵 Price Per Night: $1,223/night
- 🛏️ Sleeps: 8 guests
- 🔥 Unique Features: Pool with waterfall, pet-friendly, parking, outdoor grill
- 🌟 Perfect For: Family getaways 👨👩👧👦, group vacations 🏖️, relaxation seekers 🌅
Experience the charm of Chick-A-Pea Cottage in the heart of Key West. This 4-bedroom, 2.5-bathroom cottage features a stunning pool with a waterfall.
It’s just a short walk to Duval Street, known for its lively shops and restaurants. Explore the Ernest Hemingway House, a historic landmark, and visit the Southernmost Point, a popular photo spot marking the southern tip of the U.S.
Enjoy the spacious open-concept living and dining areas, perfect for gatherings. Step outside to relax by the pool surrounded by lush palm trees and Bougainvillea.
The fully equipped kitchen makes family meals easy, and outdoor dining with a grill adds a touch of magic to evenings under the stars. This cottage offers the perfect balance of peaceful retreat and proximity to Key West’s vibrant attractions.
11. Cozy & Relaxing Vacation Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $643/night
- 🛏️ Sleeps: 4 guests
- 🔥 Unique Features: Separate cottage & main house, private backyard, pool
- 🌟 Perfect For: Couples 👩❤️👨, friends’ getaways 🍹, privacy seekers 🌿
Discover this cozy vacation home, a private tropical retreat featuring a pool and two separate living spaces. Located in a quiet residential neighborhood, this getaway combines indoor-outdoor island living.
The main house and detached cottage each offer a king bedroom and a full bathroom. Inside, enjoy a fully renovated kitchen, spacious living area, and cozy dining spots for relaxed meals.
Step out to a lush, fully fenced backyard with a sparkling pool, outdoor dining area, and serene palm-lined surroundings—ideal for sunbathing, cocktails, or grilling under the stars.
Just a short walk to Duval Street, famous for its shops, and South Beach for swimming. This vacation home offers the perfect blend of island culture, local attractions, and peaceful relaxation.
12. Palms-Away Home
- 📍 Location: Key West, FL
- 💵 Price Per Night: $403/night
- 🛏️ Sleeps: 6 guests
- 🔥 Unique Features: Community pool, private patio, parking, concierge service
- 🌟 Perfect For: Group getaways 👨👩👧👦, relaxation seekers 🌅, adventure lovers 🌴
Relax at Palms Away, a charming 2-bedroom, 1.5-bathroom townhome in the coveted Truman Annex community. This cozy home offers a private porch, an open-concept living area, and a fully equipped kitchen with granite countertops.
The bedrooms have flat-screen TVs and French doors leading to a private balcony with tropical views. Enjoy the community pool and outdoor grilling area, perfect for relaxing after a day of exploration.
Visit Fort Zachary Taylor State Park for its historic fort and serene beach. Discover Harry Truman’s Little White House, a historic landmark, or unwind at Truman Annex Waterfront Park, offering stunning views and a relaxing atmosphere.
Relax at Palms Away, your perfect Key West retreat, with a pool, prime location, and easy access to local attractions.
13. Riptides Apartment
- 📍 Location: Key West, FL
- 💵 Price Per Night: $304/night
- 🛏️ Sleeps: 2 guests
- 🌟 Unique Features: Stylish studio, private deck, kitchenette, and central location
- 🔥 Perfect For: Couples 💑, Key West explorers 🌴, and weekend getaways 🌅
Riptides offers a stylish studio just a block from Duval Street, Key West’s vibrant heart. This cozy 480 sq. ft. space features a queen bed, a kitchenette, and a dining table for two.
Enjoy private outdoor seating on the deck or explore nearby attractions like the Ernest Hemingway Home and Museum and the Southernmost Point.
Riptides is also ideally located for beach lovers, with easy access to Simonton Beach and Fort Zachary Taylor Beach. Indulge in local dining at Better Than Sex, Duffy’s, and Pisces, or relax at Higgs Beach and South Beach.
Whether you’re enjoying the vibrant scene or unwinding at the beach, Riptides puts you at the center of it all for a truly unforgettable Key West experience.
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