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13 Finest Trip Leases in Key West


Dreaming of visiting the Florida Keys someday within the close to future? Searching for a trip rental in Key West with unmatched entry to water actions? Expertise the very best that Key West has to supply at one among these trip leases.

The Florida Keys are a slice of paradise within the Sunshine State, beloved for its attractive tropical landscapes, out of doors water adventures, and laid-back setting. Key West sits within the coronary heart of a picturesque string of islands. There’s a lengthy listing of issues to do when visiting the southernmost metropolis in the USA, from scuba diving, snorkeling, and seaside hopping to indulging within the metropolis’s well-known key lime pie.

One of the simplest ways to expertise this colourful metropolis is by staying native, as you’ll have easy accessibility to town’s high sights and island actions. These charming Key West trip leases additionally add inviting perks like out of doors swimming pools, non-public balconies, and a central location close to the vigorous Duval Road.

Disclosure: This text on the very best trip leases in Key West incorporates affiliate hyperlinks, the place I’ll obtain a small fee at no further value to you.

Trip Leases in Key West: Prime Stays in Key West, FL

Listed below are the very best trip leases in Key West, FL, by class, contemplating elements together with facilities, journey varieties, and budgets. The next sections will cowl every itemizing in additional element.

Excellent Rental for Pool Actions: Situated in Outdated City Key West

Superior Rental for Peace and Quiet: Provides Whole Pivacy for Company

Prime Keep for Structure Fanatics: Combines Outdated and New Designs

Finest Trip Spot for Romantics: Rental Meant to Accommodate 2 Company

Elite Rental for These Looking for Facilities: Award-Successful Grasp Suite

Nice Trip Rental for Luxurious Dwelling: Situated Close to Duval Road

Finest Rental for Vacationers with Pets: Entry to Points of interest, Non-public Facilities

Prime Trip House for Historical past Buffs: Options Pristine Poolside Structure

Finest Rental in a Neighborhood Ambiance: Just lately Renovated Inside

Prime Possibility for Metropolis Dwelling: Situated within the Truman Annex Neighborhood

Elite Rental for Nature Lovers: Surrounded by Tropical, Floral Surroundings

Nice Trip Rental for Chilling Out: Comes with a Lengthy Checklist of Facilities

Cozy Rental with a Non-public Pool: Distinct Unit with a Distinctive Structural Flare

13 Trip Leases in Key West: Prime Trip Houses in FL

Discovering a gorgeous trip rental surrounded by seashores and island landscapes has by no means been so easy! With our listing of the 13 greatest trip leases in Key West, you’ll be handled to enjoyable actions, luxurious facilities, and the very best the tropical life has to supply. Take a look at all 13 choices beneath!

1. Mango Margarita – 2-Bed room Rental in Key West

Location: Key West, Florida

Charges from: $722 per night time

Accommodates: 6 friends

The pool outside of this rental in Key West is shown.
This Key West rental house is an ideal match for folk who need to hang around by the pool. | VRBO
The exterior of this rental is shown.
Benefit from the Florida breezes that come by way of the numerous home windows of this rental. | VRBO

Not solely does this two-bedroom trip rental in Key West have probably the most cute title, however it has a handy Outdated City location. Only a block from Duval and a brief stroll or bike trip to every part in Key West, this rental features a totally stocked kitchen, a comfortable front room with a flat-screen TV, and two bedrooms with en suite baths. 

Step out to your non-public out of doors dwelling area to discover a heated pool and coated deck with a desk for hanging out or eating alfresco, whereas the solar loungers across the pool and a propane grill are the right addition to take pleasure in Key West’s sunny days. 

2. Romantic Key West Rental House – Voted Prime 25 in USA

Location: Key West, Florida

Charges from: $425 per night time

Accommodates: 2 friends

The interior of the rental is shown.
This Key West trip rental is ranked as one of many easiest of its variety. | VRBO
The back porch of this Key West vacation renal is shown.
The again porch of this rental can be utilized for rest throughout the day or night time. | VRBO

Dubbed one of the crucial romantic Key West trip leases, this award-winning Master bedroom has 17-foot vaulted ceilings to create an ethereal, open area. An ideal area for 2, the “little jewel” is tucked away inside a lush tropical backyard, simply steps from the seashores. 

Along with a vibrant palette of colours and eclectic decor, you’ll discover 600 thread depend sheets that guarantee a blissful night time of sleep. The moist bar has a wraparound bar, barstools, and a kitchenette with a mini fridge and microwave, whereas the huge jetted tub is large enough for 2. Outdoors, there’s a spacious shared deck with cozy seating and a BBQ grill.

3. Blue Bungalow – 2-Bed room Key West Trip Rental with Pool

Location: Key West, Florida

Charges from: $408 per night time

Accommodates: 6 friends

This vacation rental in Key West is known as the Blue Bungalow.
Keep at this rental in Key West and benefit from the floral surroundings. | VRBO
The clean interior of the rental is shown.
The inside of this charming rental is vibrant and tidy. | VRBO

The Blue Bungalow townhome embodies the appeal of Key West, surrounded by swaying palms and a picturesque white picket fence. The 2-bedroom Key West rental house accommodates as much as six friends, with an open flooring plan on its decrease stage, a completely geared up kitchen, a bar high with seating, and an indoor eating desk for sharing meals. 

Upstairs are two visitor bedrooms, one with a writing desk for these working remotely and a washer/dryer. Its out of doors dwelling area is a spotlight, that includes a coated area with a eating space and electrical grill, whereas a neighborhood pool is steps away.   

4. William Skelton House – Trip Rental in Key West

Location: Key West, Florida

Charges from: $1,250 per night time

Accommodates: 14 friends

The pool and lighted deck of this rental are shown.
You’ll have entry to an unimaginable poolside spot while you keep at this luxurious trip rental in Key West. | VRBO
The interior of this Key West rental home is shown.
The comfortable inside of this rental is certain to please you and your friends. | VRBO

Go all out in your subsequent trip with this spacious six-bedroom rental in Key West that may accommodate as much as 14 friends. Everybody within the group can have room to stretch out on the William Skelton “Pink Home,” situated simply steps away from Duval Road within the coronary heart of Outdated City Key West. 

The historic house additionally has a personal yard with a pool, two spacious dwelling rooms, and shaded patios and porches. It’s a wonderful choice for household reunions and huge teams, who can make the most of the totally furnished house with Victorian accents, geared up kitchen, and parking area. 

5. Pineapple Cottage – 2-Bed room Rental in Key West with Non-public Pool

Location: Key West, Florida

Charges from: $404 per night time

Accommodates: 5 friends

The pool outside of the Pineapple Cottage, a Key West rental home, is shown.
Dive into the pristine pool waters of this attractive Key West trip rental. | VRBO
This rental's interior is shown.
This rental is the right place to remain throughout a household trip. | VRBO

Among the best trip leases in Key West with a personal pool, this two-bedroom property is in Outdated City. Solely a 1/2 block from Duval Road, the tropical oasis provides complete privateness with a spacious yard that incorporates a deck, glowing pool, charcoal grill, cozy seating, and luxurious tropical landscaping. 

French doorways result in an open dwelling space and kitchen area that creates an ethereal ambiance, whereas a completely geared up leisure system and board video games will maintain everybody within the group entertained. The 2nd flooring additionally has a big dwelling area with a settee and flat-screen TV.

6. Pilar’s Secret – Key West Rental House Proper Off Duval Road

Location: Key West, Florida

Charges from: $1,057 per night time

Accommodates: 8 friends

The gorgeous exterior of this Key West rental is shown.
Keep at this trip rental in Key West for straightforward entry to Duval Road. | VRBO
The interior of this vacation rental in Key West is shown.
You’ll be able to take pleasure in the great thing about this rental from the consolation of the lounge. | VRBO

For a dose of luxurious, e book a keep at this well-appointed three-bedroom Key West trip rental. Accommodating as much as eight friends, it’s simply half a block off Duval Road and on a quiet, nondescript lane. 

Better of all, it has a personal pool surrounded by chaise lounges the place you’ll be able to cool off with a dip, whereas the out of doors dwelling space with a BBQ grill, a completely geared up kitchen, and a big indoor dwelling area makes it a simple choose to your Florida journey.

7. Key West Trip Rental within the Truman Annex

Location: Key West, Florida

Charges from: $364 per night time

Accommodates: 4 friends

This Key West vacation rental is shown from the inside.
This trip rental in Key West is simply the proper keep for a pair of {couples} on the lookout for a getaway. | VRBO
The hot tub and back deck of the rental are shown.
For these on the lookout for facilities at their subsequent trip house, this choice may be for you. | VRBO

Making this two-bedroom Key West rental house your subsequent trip keep is simple. Situated within the famend Truman Annex in Outdated City, it’s inside strolling distance from town’s high eating places, bars, outlets, and nightlife and a motorcycle trip away from Fort Zachary Seaside State Park. 

However there are many causes to remain on-site, because it boasts a personal sizzling tub on its again patio and a vibrant, ethereal first-floor front room space for hanging out. There’s additionally a well-equipped kitchen, French doorways that open to a balcony, and a close-by neighborhood pool.  

8. Renovated Rental in Key West with Shared Pool & Sizzling Tub

Location: Key West, Florida

Charges from: $380 per night time

Accommodates: 6 friends

This outside of the renovated rental complex is shown.
This renovated rental in Key West options entry to a pool and a sizzling tub. | VRBO
The interior of the rental in Key West is shown.
You’ll be able to’t beat the views from the balcony of this trip rental. | VRBO

This two-bedroom rental in Key West was lately renovated on the Dawn Suites Resort and features a model new inside. Along with top-of-the-line home equipment, fixtures, and furnishings, it incorporates a new Samsung Sensible TV in every bed room and a 60-inch in the lounge. 

On the finish of your day in Key West, sit again and benefit from the sundown views over the salt ponds out of your non-public balcony. You can even make the most of perks like a Keurig espresso machine, a full-size washer and dryer, and a neighborhood pool, sizzling tub, gymnasium, and tennis courtroom. 

9. Mango Cottage – Trip Rental in Key West with Non-public Pool

Location: Key West, Florida

Charges from: $388 per night time

Accommodates: 6 friends

This rental in Key West is known as the Mango Cottage.
The Mango Cottage is likely one of the premier Key West rental properties accessible. | VRBO
The interior of the rental is shown.
You’ll be able to keep at this improbable rental for an excellent worth. | VRBO

It’s laborious to not be pulled in by the appeal of the Mango Cottage, a 2-bedroom rental in Key West with a personal pool. The recently-restored historic Conch home has vintage Miami-Dade County pine partitions and flooring, along with trendy options like an open-concept kitchen, dwelling, and eating space that allow in pure mild from its vaulted ceilings and glass doorways. 

The out of doors deck space is a spotlight for a lot of, the place you’ll be able to take pleasure in out of doors eating underneath umbrella shade, high up your tan on the lounge chairs, or sip cocktails on the deck across the heated pool. 

10. Chick-A-Pea Cottage – Key West Rental House, 1 Block to Duval

Location: Key West, Florida

Charges from: $1,976 per night time

Accommodates: 8 friends

This Key West vacation rental and the white fence in front of it are shown.
Although this trip rental in Key West appears small from the skin, it will probably accommodate as much as eight friends. | VRBO
The living area and dining room of the rental are shown.
This rental is likely one of the most sought-after stays within the Florida Keys. | VRBO

Probably the most common trip leases in Key West, this massive four-bedroom cottage has undergone a whole renovation. It’s the right mix of appeal and historic options with sufficient area for as much as eight friends, with added luxuries like a personal pool, a cabana with a settee and lounge, and a BBQ for grilling. 

The pet-friendly house is completely non-public, with a fenced-in yard. While you’re able to discover, the Ernest Hemingway Home and Museum are seconds away, whereas the motion on Duval Road is a 1/2 block from the house.  

11. Casa Amor – 3-Bed room Key West Trip Rental with Non-public Pool

Location: Key West, Florida

Charges from: $656 per night time

Accommodates: 10 friends

This vacation rental in Key West's exterior, as well as its pool, are shown.
This rental in Key West incorporates a cozy poolside setup and a detailed proximity to the character of southern Florida. | VRBO
The unique exterior of the rental is shown.
The distinctive construction of this rental is eye-catching and sensible for friends. | VRBO

Previously used as a bottling plant, this three-bedroom house is likely one of the hottest trip leases in Key West. The tropical retreat is an award-winning getaway, having obtained a prestigious Ceramic Star for Architectural Preservation Wonderful, and features a lengthy listing of luxe facilities. 

Its vibrant and open area consists of excessive ceilings and pure mild, an up to date kitchen and an open idea dwelling space with a flat-screen and comfy furnishings. Its indoor/out of doors area is ideal for entertaining, with the ethereal patio that includes a lap pool, out of doors bathe, and fuel grill.  

12. Palms Away – Truman Annex Trip Rental in Key West

Location: Key West, Florida

Charges from: $280 per night time

Accommodates: 6 friends

This Truman Annex rental is shown from a nearby street corner.
This Key West trip rental is the right spot for teams on a funds. | VRBO
The staircase and dining area of this Key West rental home are shown.
This rental is situated proper within the coronary heart of Key West. | VRBO

If location is what you’re after, this two-bedroom Key West rental house is within the coronary heart of town. Nonetheless, this charming rental, set within the extremely coveted neighborhood of Truman Annex, is surrounded by palm timber and white picket fences. 

Unwind in paradise in your non-public porch or discover the open idea nice room with an up to date kitchen and breakfast bar. The tropical decor creates a laid-back vibe, whereas the indoor/out of doors area is nice for completely happy hour cocktails, that includes glass sliding doorways that open to a personal out of doors space with a eating desk and electrical grill.

13. Riptides – Centrally Situated, Trendy Rental in Key West 

Location: Key West, Florida

Charges from: $348 per night time

Accommodates: 2 friends

This blue and white Key West rental home is shown.
{Couples} can have a tough time discovering a extra handy spot to remain than this Key West rental house. | VRBO
The bedroom of the rental is shown.
Use this rental to your subsequent romantic getaway by the seaside. | VRBO

Love birds on the lookout for a trendy area can e book a keep at this rental in Key West, situated one block from Duval Road. The comfortable trip rental on Simonton Road is ideal for a no-frills romantic getaway in Key West, that includes a queen-size mattress, kitchenette, desk for 2, and separate lavatory. 

You gained’t even want a automotive for the size of your keep, as every part is inside strolling or biking distance away. After sightseeing, you’ll be able to benefit from the small non-public out of doors deck with patio seating.



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