13 Best Vacation Rentals in Key West: Top Vacation Homes in FL

by clients@lseo.com

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.

Disclosure: This article on the best vacation rentals in Key West contains affiliate links, where I may receive a small commission at no extra cost to you.

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

The pool outside of this rental in Key West is shown.
This Key West rental home is a perfect fit for folks who want to hang out by the pool. | VRBO
The exterior of this rental is shown.
Enjoy the Florida breezes that come through the many windows of this rental. | VRBO

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

The interior of the rental is shown.
This Key West vacation rental is ranked as one of the very best of its kind. | VRBO
The back porch of this Key West vacation renal is shown.
The back porch of this rental can be used for relaxation during the day or night. | VRBO

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

This vacation rental in Key West is known as the Blue Bungalow.
Stay at this rental in Key West and enjoy the floral scenery. | VRBO
The clean interior of the rental is shown.
The interior of this charming rental is bright and tidy. | VRBO

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

The pool and lighted deck of this rental are shown.
You will have access to an incredible poolside spot when you stay at this luxury vacation rental in Key West. | VRBO
The interior of this Key West rental home is shown.
The cozy interior of this rental is sure to please you and your guests. | VRBO

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

The pool outside of the Pineapple Cottage, a Key West rental home, is shown.
Dive into the pristine pool waters of this gorgeous Key West vacation rental. | VRBO
This rental's interior is shown.
This rental is the perfect place to stay during a family vacation. | VRBO

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

The gorgeous exterior of this Key West rental is shown.
Stay at this vacation rental in Key West for easy access to Duval Street. | VRBO
The interior of this vacation rental in Key West is shown.
You can enjoy the beauty of this rental from the comfort of the living room. | VRBO

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

This Key West vacation rental is shown from the inside.
This vacation rental in Key West is just the right stay for a pair of couples looking for a getaway. | VRBO
The hot tub and back deck of the rental are shown.
For those looking for amenities at their next vacation home, this selection might be for you. | VRBO

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 outside of the renovated rental complex is shown.
This renovated rental in Key West features access to a pool and a hot tub. | VRBO
The interior of the rental in Key West is shown.
You can’t beat the views from the balcony of this vacation rental. | VRBO

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

This rental in Key West is known as the Mango Cottage.
The Mango Cottage is one of the premier Key West rental homes available. | VRBO
The interior of the rental is shown.
You can stay at this fantastic rental for an outstanding price. | VRBO

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

This Key West vacation rental and the white fence in front of it are shown.
Though this vacation rental in Key West looks small from the outside, it can accommodate up to eight guests. | VRBO
The living area and dining room of the rental are shown.
This rental is one of the most sought-after stays in the Florida Keys. | VRBO

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

This vacation rental in Key West's exterior, as well as its pool, are shown.
This rental in Key West features a cozy poolside setup and a close proximity to the nature of southern Florida. | VRBO
The unique exterior of the rental is shown.
The unique structure of this rental is eye-catching and practical for guests. | VRBO

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

This Truman Annex rental is shown from a nearby street corner.
This Key West vacation rental is the perfect spot for groups on a budget. | VRBO
The staircase and dining area of this Key West rental home are shown.
This rental is located right in the heart of Key West. | VRBO

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

This blue and white Key West rental home is shown.
Couples will have a hard time finding a more convenient spot to stay than this Key West rental home. | VRBO
The bedroom of the rental is shown.
Use this rental for your next romantic getaway by the beach. | VRBO

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.

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