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13 Finest Trip Leases in Key West


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

The Florida Keys are a slice of paradise within the Sunshine State, beloved for its beautiful 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 US, 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 quick access to town’s prime points of interest 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 Avenue.

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

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

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

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

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

Prime Keep for Structure Fans: Combines Previous and New Designs

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

Elite Rental for These In search of Facilities: Award-Successful Grasp Suite

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

Finest Rental for Vacationers with Pets: Entry to Sights, Personal Facilities

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

Finest Rental in a Neighborhood Environment: 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 Personal Pool: Distinct Unit with a Distinctive Structural Flare

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

Discovering a fantastic trip rental surrounded by seashores and island landscapes has by no means been so easy! With our listing of the 13 finest trip leases in Key West, you’ll be handled to enjoyable actions, luxurious facilities, and one of the 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 residence is an ideal match for people 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 various 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 Previous City location. Only a block from Duval and a brief stroll or bike experience to every little thing in Key West, this rental features a totally stocked kitchen, a snug front room with a flat-screen TV, and two bedrooms with en suite baths. 

Step out to your non-public out of doors residing area to discover a heated pool and lined 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 leisure in the course of the day or night time. | VRBO

Dubbed some of the romantic Key West trip leases, this award-winning Main 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 attraction of Key West, surrounded by swaying palms and a picturesque white picket fence. The 2-bedroom Key West rental residence accommodates as much as six friends, with an open ground plan on its decrease stage, a totally geared up kitchen, a bar prime 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 residing area is a spotlight, that includes a lined area with a eating space and electrical grill, whereas a group 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 should have entry to an unbelievable poolside spot if 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 bound 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,” positioned simply steps away from Duval Avenue within the coronary heart of Previous City Key West. 

The historic residence additionally has a non-public yard with a pool, two spacious residing rooms, and shaded patios and porches. It’s a wonderful possibility for household reunions and huge teams, who can reap the benefits of the totally furnished residence with Victorian accents, geared up kitchen, and parking area. 

5. Pineapple Cottage – 2-Bed room Rental in Key West with Personal 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 beautiful Key West trip rental. | VRBO
This rental's interior is shown.
This rental is the right place to remain throughout a household trip. | VRBO

Top-of-the-line trip leases in Key West with a non-public pool, this two-bedroom property is in Previous City. Solely a 1/2 block from Duval Avenue, the tropical oasis presents complete privateness with a spacious yard that contains a deck, glowing pool, charcoal grill, cozy seating, and plush tropical landscaping. 

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

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

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 simple entry to Duval Avenue. | VRBO
The interior of this vacation rental in Key West is shown.
You’ll be able to take pleasure in the fantastic 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 Avenue and on a quiet, nondescript lane. 

Better of all, it has a non-public pool surrounded by chaise lounges the place you possibly can cool off with a dip, whereas the out of doors residing space with a BBQ grill, a totally geared up kitchen, and a big indoor residing area makes it a straightforward decide on 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 best keep for a pair of {couples} in search of a getaway. | VRBO
The hot tub and back deck of the rental are shown.
For these in search of facilities at their subsequent trip residence, this choice may be for you. | VRBO

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

However there are many causes to remain on-site, because it boasts a non-public scorching 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 group 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 scorching 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 contains a new Samsung Good 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 reap the benefits of perks like a Keurig espresso machine, a full-size washer and dryer, and a group pool, scorching tub, gymnasium, and tennis court docket. 

9. Mango Cottage – Trip Rental in Key West with Personal 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 among the premier Key West rental properties out there. | VRBO
The interior of the rental is shown.
You’ll be able to keep at this improbable rental for an impressive value. | VRBO

It’s arduous to not be pulled in by the attraction of the Mango Cottage, a 2-bedroom rental in Key West with a non-public 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, residing, and eating space that permit in pure gentle from its vaulted ceilings and glass doorways. 

The out of doors deck space is a spotlight for a lot of, the place you possibly can take pleasure in out of doors eating underneath umbrella shade, prime 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 seems to be small from the skin, it might probably accommodate as much as eight friends. | VRBO
The living area and dining room of the rental are shown.
This rental is among the most sought-after stays within the Florida Keys. | VRBO

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

The pet-friendly house is fully 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 Avenue is a 1/2 block from the house.  

11. Casa Amor – 3-Bed room Key West Trip Rental with Personal 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 contains 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 residence is among the hottest trip leases in Key West. The tropical retreat is an award-winning getaway, having obtained a prestigious Ceramic Star for Architectural Preservation Glorious, and features a lengthy listing of luxe facilities. 

Its vibrant and open area contains excessive ceilings and pure gentle, an up to date kitchen and an open idea residing space with a flat-screen and comfortable 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 price range. | VRBO
The staircase and dining area of this Key West rental home are shown.
This rental is positioned proper within the coronary heart of Key West. | VRBO

If location is what you’re after, this two-bedroom Key West rental residence is within the coronary heart of town. Nonetheless, this charming rental, set within the extremely coveted group 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 comfortable hour cocktails, that includes glass sliding doorways that open to a non-public out of doors space with a eating desk and electrical grill.

13. Riptides – Centrally Situated, Fashionable 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 residence. | VRBO
The bedroom of the rental is shown.
Use this rental on your subsequent romantic getaway by the seaside. | VRBO

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

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

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