Dreaming of visiting the Florida Keys sometime in the near future? Looking for a vacation rental in Key West with unmatched access to water activities? Experience the best that Key West has to offer at one of these vacation rentals.
The Florida Keys are a slice of paradise in the Sunshine State, beloved for its gorgeous tropical landscapes, outdoor water adventures, and laid-back setting. Key West sits in the heart of a picturesque string of islands. There is a long list of things to do when visiting the southernmost city in the United States, from scuba diving, snorkeling, and beach hopping to indulging in the city’s famous key lime pie.
The best way to experience this colorful city is by staying local, as you’ll have easy access to the city’s top attractions and island activities. These charming Key West vacation rentals also add inviting perks like outdoor pools, private balconies, and a central location near the lively Duval Street.
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.
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 – 2-Bedroom Rental in Key West
Location: Key West, Florida
Rates from: $722 per night
Accommodates: 6 guests
Not only does this two-bedroom vacation rental in Key West have the most adorable name, but it has a convenient Old Town location. Just a block from Duval and a short walk or bike ride to everything in Key West, this rental includes a fully stocked kitchen, a comfy living room with a flat-screen TV, and two bedrooms with en suite baths.
Step out to your private outdoor living space to find a heated pool and covered deck with a table for hanging out or dining alfresco, while the sun loungers around the pool and a propane grill are the perfect addition to enjoy Key West’s sunny days.
2. Romantic Key West Rental Home – Voted Top 25 in USA
Location: Key West, Florida
Rates from: $425 per night
Accommodates: 2 guests
Dubbed one of the most romantic Key West vacation rentals, this award-winning Master suite has 17-foot vaulted ceilings to create an airy, open space. A perfect space for two, the “little jewel” is tucked away inside a lush tropical garden, just steps from the beaches.
In addition to a vibrant palette of colors and eclectic decor, you’ll find 600 thread count sheets that ensure a blissful night of sleep. The wet bar has a wraparound bar, barstools, and a kitchenette with a mini fridge and microwave, while the vast jetted tub is big enough for two. Outside, there’s a spacious shared deck with comfy seating and a BBQ grill.
3. Blue Bungalow – 2-Bedroom Key West Vacation Rental with Pool
Location: Key West, Florida
Rates from: $408 per night
Accommodates: 6 guests
The Blue Bungalow townhome embodies the charm of Key West, surrounded by swaying palms and a picturesque white picket fence. The two-bedroom Key West rental home accommodates up to six guests, with an open floor plan on its lower level, a fully equipped kitchen, a bar top with seating, and an indoor dining table for sharing meals.
Upstairs are two guest bedrooms, one with a writing table for those working remotely and a washer/dryer. Its outdoor living space is a highlight, featuring a covered space with a dining area and electric grill, while a community pool is steps away.
4. William Skelton Home – Vacation Rental in Key West
Location: Key West, Florida
Rates from: $1,250 per night
Accommodates: 14 guests
Go all out on your next vacation with this spacious six-bedroom rental in Key West that can accommodate up to 14 guests. Everyone in the group will have room to stretch out at the William Skelton “Pink House,” located just steps away from Duval Street in the heart of Old Town Key West.
The historic home also has a private backyard with a pool, two spacious living rooms, and shaded patios and porches. It’s an excellent option for family reunions and large groups, who can take advantage of the fully furnished home with Victorian accents, equipped kitchen, and parking space.
5. Pineapple Cottage – 2-Bedroom Rental in Key West with Private Pool
Location: Key West, Florida
Rates from: $404 per night
Accommodates: 5 guests
One of the best vacation rentals in Key West with a private pool, this two-bedroom property is in Old Town. Only a 1/2 block from Duval Street, the tropical oasis offers total privacy with a spacious backyard that features a deck, sparkling pool, charcoal grill, comfy seating, and lush tropical landscaping.
French doors lead to an open living area and kitchen space that creates an airy atmosphere, while a fully equipped entertainment system and board games will keep everyone in the group entertained. The 2nd floor also has a large living space with a sofa and flat-screen TV.
6. Pilar’s Secret – Key West Rental Home Right Off Duval Street
Location: Key West, Florida
Rates from: $1,057 per night
Accommodates: 8 guests
For a dose of luxury, book a stay at this well-appointed three-bedroom Key West vacation rental. Accommodating up to eight guests, it’s just half a block off Duval Street and on a quiet, nondescript lane.
Best of all, it has a private pool surrounded by chaise lounges where you can cool off with a dip, while the outdoor living area with a BBQ grill, a fully equipped kitchen, and a large indoor living space makes it an easy pick for your Florida adventure.
7. Key West Vacation Rental in the Truman Annex
Location: Key West, Florida
Rates from: $364 per night
Accommodates: 4 guests
Making this two-bedroom Key West rental home your next vacation stay is easy. Located in the renowned Truman Annex in Old Town, it’s within walking distance from the city’s top restaurants, bars, shops, and nightlife and a bike ride away from Fort Zachary Beach State Park.
But there are plenty of reasons to stay on-site, as it boasts a private hot tub on its back patio and a bright, airy first-floor living room area for hanging out. There’s also a well-equipped kitchen, French doors that open to a balcony, and a nearby community pool.
8. Renovated Rental in Key West with Shared Pool & Hot Tub
Location: Key West, Florida
Rates from: $380 per night
Accommodates: 6 guests
This two-bedroom rental in Key West was recently renovated at the Sunrise Suites Resort and includes a brand new interior. In addition to top-of-the-line appliances, fixtures, and furnishings, it features a new Samsung Smart TV in each bedroom and a 60-inch in the living room.
At the end of your day in Key West, sit back and enjoy the sunset views over the salt ponds from your private balcony. You can also take advantage of perks like a Keurig coffee machine, a full-size washer and dryer, and a community pool, hot tub, gym, and tennis court.
9. Mango Cottage – Vacation Rental in Key West with Private Pool
Location: Key West, Florida
Rates from: $388 per night
Accommodates: 6 guests
It’s hard not to be pulled in by the charm of the Mango Cottage, a 2-bedroom rental in Key West with a private pool. The recently-restored historic Conch house has antique Miami-Dade County pine walls and floors, in addition to modern features like an open-concept kitchen, living, and dining area that let in natural light from its vaulted ceilings and glass doors.
The outdoor deck area is a highlight for many, where you can enjoy outdoor dining under umbrella shade, top up your tan on the lounge chairs, or sip cocktails on the deck around the heated pool.
10. Chick-A-Pea Cottage – Key West Rental Home, 1 Block to Duval
Location: Key West, Florida
Rates from: $1,976 per night
Accommodates: 8 guests
One of the most popular vacation rentals in Key West, this large four-bedroom cottage has undergone a complete renovation. It’s the perfect blend of charm and historic features with enough space for up to eight guests, with added luxuries like a private pool, a cabana with a sofa and lounge, and a BBQ for grilling.
The pet-friendly home is entirely private, with a fenced-in yard. When you’re ready to explore, the Ernest Hemingway House and Museum are seconds away, while the action on Duval Street is a 1/2 block from the home.
11. Casa Amor – 3-Bedroom Key West Vacation Rental with Private Pool
Location: Key West, Florida
Rates from: $656 per night
Accommodates: 10 guests
Formerly used as a bottling plant, this three-bedroom home is one of the most popular vacation rentals in Key West. The tropical retreat is an award-winning getaway, having received a prestigious Ceramic Star for Architectural Preservation Excellent, and includes a long list of luxe amenities.
Its bright and open space includes high ceilings and natural light, an updated kitchen and an open concept living area with a flat-screen and cozy furnishings. Its indoor/outdoor space is perfect for entertaining, with the airy patio featuring a lap pool, outdoor shower, and gas grill.
12. Palms Away – Truman Annex Vacation Rental in Key West
Location: Key West, Florida
Rates from: $280 per night
Accommodates: 6 guests
If location is what you’re after, this two-bedroom Key West rental home is in the heart of the city. However, this charming rental, set in the highly coveted community of Truman Annex, is surrounded by palm trees and white picket fences.
Unwind in paradise on your private porch or explore the open concept great room with an updated kitchen and breakfast bar. The tropical decor creates a laid-back vibe, while the indoor/outdoor space is great for happy hour cocktails, featuring glass sliding doors that open to a private outdoor area with a dining table and electric grill.
13. Riptides – Centrally Located, Stylish Rental in Key West
Location: Key West, Florida
Rates from: $348 per night
Accommodates: 2 guests
Love birds looking for a stylish space can book a stay at this rental in Key West, located one block from Duval Street. The cozy vacation rental on Simonton Street is perfect for a no-frills romantic getaway in Key West, featuring a queen-size bed, kitchenette, table for two, and separate bathroom.
You won’t even need a car for the length of your stay, as everything is within walking or biking distance away. After sightseeing, you can enjoy the small private outdoor deck with patio seating.
