Key West, Florida, United States

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$12,135Per Month

921 Whitehead St Lighthouse Villa Key West, FL#5377060

  • 3 Bed
  • 4.5 Bath
  • $12,135

In the midst of many historic sites this home has all the updated amenities for you and your family to enjoy plus be within walking distance of the Southernmost Point. This timeless private conch home just steps away from the Hemingway House and the Key West Lighthouse a perfect location to be close to great restaurants and shops. The tropically inspired three level home offers privacy separating your entertaining spaces from your tranquil sleeping spaces. Enjoy the main level space with your up

$8,135Per Month

1609 Sunshine Dr Cayo Hueso Sunshine Key West, FL#5377031

  • 2 Bed
  • 3 Bath
  • $8,135

Monthly/Seasonal Rental Awaken your senses with tropical breezes, turquoise waters and Key West Sunshine in this brand new 2-bedroom, den, 3-bath home. A secluded location yet the best of both worlds allows you an easy stroll over to the sandy shores of Smather's Beach or just a few blocks from the entertainment of Duval Street. An ideal location to explore all the wonders of our island. Every day in Cayo Hueso Sunshine is a new adventure. An open floor plan on the main level encourage gatherin

$7,635Per Month

1430 Flagler Ave Flagler Station Key West, FL#423613

  • 3 Bed
  • 2 Bath
  • $7,635

FLAGLER STATION (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $3,200 - $7,500 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Flagler Station has been recently remodeled, refurbished and re-furnished. High speed WIFI and state-of-the-art electronics, top-of the-line gourmet kitchen and luxury linens make this home the one you'll return to year after year. Three bright and airy bedrooms and two baths. Master king-bedded bedroo

$6,635Per Month

120 Angela St Apt 202 Treetop Paradise Key West, FL#4121211

  • 2 Bed
  • 2 Bath
  • $6,635

Small quiet compound with a pool an off street parking, walking distance to great restaurants, shopping and entertainment. Relax on your balcony overlooking the saltwater pool with palm trees swaying in the breeze, a perfect picture? This lovely 2 bedroom 2 bath upstairs condo is just that. There are only 3 other condos in this secure compound that share the pool and the private outside area for lounging and grilling. Updated kitchen with granite counter tops and stainless steel appliances make

$6,435Per Month

1311 Newton St Conch Republic Retreat Key West, FL#4121261

  • 2 Bed
  • 2 Bath
  • $6,435

Historic conch home located in The Meadows, a sought out quiet neighborhood, to enjoy your private pool and outdoor space. A quintessential cigar makers shotgun style house built circa in 1890s. Located in one of the most desirable historic neighborhoods of Key West – The Meadows with tree-lined streets, a tranquil atmosphere, and yet still have easy access to the endless vacation activities available in the Southernmost City. Beaches, restaurants, tennis courts, marina, night life, everything

$6,385Per Month

903 Southard St Perfect Pineapple Key West, FL#433959

  • 2 Bed
  • 1 Bath
  • $6,385

PERFECT PINEAPPLE - (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,975 - $6,055 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Long considered a sign of hospitality, the pineapple is now widely recognized as sign of Welcome and Friendship.....and so we welcome you to the Perfect Pineapple. On the corner of Southard and Margaret streets in the historic district, this darling Key West monthly vacation rental with two bedroom

$6,385Per Month

817 Eaton St Apt 2 Lazy Gecko Key West, FL#4949695

  • 2 Bed
  • 1.5 Bath
  • $6,385

Beautifully recently remodeled 2 bed/1.5 bath condo located just 4 blocks to Duval Street and the Historic Seaport. This 2-bedroom downstairs condo offers the best of all worlds. Enter from a quiet lane into the newly painted and furnished living/dining/kitchen space. Lots of windows and french doors to let in the sunshine. Master queen bedroom is situated behind french doors with a unique bathroom ensuite. Hall bathroom has access to the tub/shower through its own private door. All stainless ki

$6,135Per Month

918 Southard St # 1 Southard Square Hideaway Key West, FL#4949694

  • 1 Bed
  • 1 Bath
  • $6,135

Amazingly Perfect!!! That is how one of our guests reviewed Southard Getaway! This amazingly perfect rental can be yours as well! Imagine it. Arrive in Key West to a beach-like home in walking distance to all that Key West has to offer. Yes, that's Southard Getaway. Two queen bedrooms upstairs with full bath, open living space downstairs with quiet, shaded deck. Decorated in hues of blue and green that remind you of the ocean a few steps away. Located in the exclusive Truman Annex gated commun

$6,025Per Month

1018 Thompson Ln Key Lime Pie Key West, FL#437029

  • 2 Bed
  • 2 Bath
  • $6,025

KEY LIME PIE: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,600 - $5,775 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) One block from the Historic Seaport and close enough to bike to all the sites and attractions of Old Town. Refurbished with updated kitchen cabinets, countertops, and appliances. On the first floor you will find the living room, kitchen, master bedroom and bathroom. On the second floor is the guest bedr

$5,935Per Month

2020 Fogarty Ave Poolside Paradise Key West, FL#4115607

  • 2 Bed
  • 2 Bath
  • $5,935

It is all about outdoor living at this beautiful private home with large covered living space overlooking your private pool. Poolside Paradise was built with entertaining in mind. Privacy fence surrounds the intimate front yard perfect for gathering, wet bar is welcome addition in the kitchen, and wait until you see the backyard! The covered outdoor living room is larger than the one indoors, just steps from the heated 18'x24' pool. Off-street parking, BBQ grill and high-tech entertainment syste

$4,835Per Month

717 Emma St Apt A Emma's Secret Key West, FL#4949755

  • 2 Bed
  • 1 Bath
  • $4,835

EMMA'S SECRET --- (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,400 - $4,525 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Luxurious 2 bedroom 1 bath Key West condo, located in a historic neighborhood of Old Town with a total of 4 condos in the building. Walking distance to Duval Street, the heart of Key West with all the restaurants, specialty shops, galleries and nightlife. Hemingway's House, Truman's Little White House

$4,835Per Month

717 Emma St Apt B Emma's Escape Key West, FL#4949756

  • 2 Bed
  • 2.5 Bath
  • $4,835

EMMA'S ESCAPE -- (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,400 - $4,525 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Beautiful and spacious Key West condo: two bedroom one bath located in historic Old Town's Bahama Village neighborhood. Emma’s Escape is one of four condos within a restored historic home. The kitchen is well appointed with upgraded appliances, granite counters, and beautiful wood cabinets. The overa

$4,735Per Month

127 Golf Club Dr Coral Breeze Key West, FL#5377029

  • 2 Bed
  • 1.5 Bath
  • $4,735

CORAL BREEZE (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,100 - $4,400 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Imagine yourself living with the vibrant golf course greens in your backyard and cool tropical breezes wafting your way. Coral Breeze has that and more. Two bedrooms share the full bath upstairs. Kitchen, dining, half bath and living room space in an open floor plan downstairs. Bright and airy living roo

$4,660Per Month

69 Golf Club Dr Bogey's Retreat Key West, FL#433630

  • 2 Bed
  • 1.5 Bath
  • $4,660

BOGEY'S RETREAT: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,100 - $4,400 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Located in the exclusive Golf Course community, allowing you to enjoy all that Key West has to offer while staying in a relaxing environment. Located in the middle of the Key West Golf Course (the only course within 50 miles). Only steps away from your choice of two spa-themed private pools, and a $50

$4,660Per Month

4 Kestral Way Kokomo Key West, FL#3058237

  • 2 Bed
  • 2.5 Bath
  • $4,660

KOKOMO (monthly rental): Everybody knows a little place like Kokomo. Now if you want to go and get away from it all go down to Kokomo. Tropical drinks melting in your hand, we'll be falling in love to the rhythm of a steel drum band down in Kokomo. It's not Bermuda or the Bahamas but better, a delightful 2 bedroom, 2.5 bathroom townhome in Key West, FL. Bright and sunny Kokomo offers plenty of space for monthly renters who want to settle in and live like a native. The main level of the home off

$4,660Per Month

169 Golf Club Dr A Little Slice of Paradise Key West, FL#4950915

  • 2 Bed
  • 1.5 Bath
  • $4,660

Townhouse located just steps from the Key West Golf Course Club House and after a round of golf head over to either of the two pools to cool off. Imagine yourself in a secluded, gated community steps from the golf course, minutes from the beach, airport and some of the local's favorite restaurants. Spend a month (or two) in A Slice of Paradise and you may never return home from this Key West monthly vacation home rental. Two bedrooms, 1 full bath upstairs; open floor plan downstairs with sleepe

$4,660Per Month

106 Golf Club Dr Wind Swept Key West, FL#5377028

  • 2 Bed
  • 1.5 Bath
  • $4,660

WIND SWEPT: (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,100 - $4,300 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Imagine yourself nestled within a serene, lushly landscaped picturesque community with walkways meandering around the only Caribbean golf course in the United States. This lovely 2 bedroom 1.5 bath Key West townhome is freshly painted and newly furnished. Enter the open and airy living space which includes

$4,585Per Month

1203 Newton St Apt 1 Newton's Nest Key West, FL#4119915

  • 1 Bed
  • 1 Bath
  • $4,585

NEWTON'S NEST (Monthly Rental) Newtons Nest (Monthly Rental) A quiet little refuge tucked away in Old Town where you can set up roost, stay for a month or more and enjoy a leisurely existence. A 1 bedroom condo that has been lovingly restored to showcase beautiful Dade County Pine walls, eclectic Key West furnishings and details along with premium bedding. Entering into the Newtons Nest you are greeted by a sunny porch with seating, the perfect spot to relax with your favorite book or lounge

$4,585Per Month

714 Olivia St Ibis Key West, FL#434029

  • 1 Bed
  • 1 Bath
  • $4,585

Ibis ( (Monthly Vacation Rental - Not Available Long Term - This Property Rents For Between $2,250 - $4,225 Base Monthly Dependent On The Time Of Year And Does Not Include Tax Or Fees) Located in The Colony compound, Ibis is a wonderful one bedroom one bath Key West rental home. Just a couple of blocks to Duval Street, walking distance to restaurants, shopping and attractions of Old Town Key West. What a great location; park your car and jump on your bike for a relaxing visit in our island ci

$3,835Per Month

409 Margaret St Apt A Windchime Key West, FL#5376869

  • Studio
  • 1 Bath
  • $3,835

Searching for an affordable monthly vacation rental in the heart of Key West? Want to have your privacy and still enjoy the best that Paradise has to offer? Then just tune into the Windchime! This lovely studio for two comes with all the comforts you need for an extended stay away from home, along with a great location in Old Town! Nestled in a quaint neighborhood in Key West's Historic Seaport District, this warm studio apartment lies within a few blocks' walk of dozens of restaurants and bars

$3,025Per Month

816-4 South Street 816-4 South Street Key West, FL#5283290

  • 1 Bed
  • 1 Bath
  • $3,025

Furnished 1 Bedroom 1 Bath with Shared Pool in the Casa Marina Neighborhood - Available Early January till Early July. This spacious and furnished second-floor, 1 bedroom 1 bath condo is located in the South Park Condominiums in the Casa Marina neighborhood. This home offers AC, dishwasher, washer/dryer in unit, back deck, and one assigned off-street parking space.The South Park Community has a wonderful pool surrounded by lush landscaping and a great location! Easy walking and biking to shops,

$3,000Per Month

3930 S Roosevelt Blvd 3930 S Roosevelt Blvd Key West, FL#5455406

  • 3 Bed
  • 2 Bath
  • $3,000

Condo in Key West - Property Id: 85320 New appliances, carpet and paint. 3 covered assigned parking spots. First, last and security deposit required. Apply at TurboTenant: http://turbo.rent/s/85320p Property Id 85320 No Pets Allowed (RLNE5266639) Amenities Other - Heating System: Forced Air Other - Cable Ready Other - Floor Covering: Tile Other - Floor Covering: Carpet Other - Cooling System: Ce

$3,000Per Month

2915 Seidenberg Avenue 2915 Seidenberg Avenue Key West, FL#5468585

  • 3 Bed
  • 2 Bath
  • $3,000

3 Bedroom 2 Bathroom House - This 3 bedroom 2 bathroom house sits in a sought after quiet neighborhood in new town. Living room with bonus Florida room. One of the bathroom has been renovated. Hardwood floors throughout. Wall unit air conditioners with jalousie windows. The laundry room is accessible from inside the house. Backyard has a deck and beach style BBQ grill. Off street parking. No Pets Allowed (RLNE5276383) Amenities No

$2,725Per Month

3812 Duck Ave 3812 Duck Ave Key West, FL#5500256

  • 2 Bed
  • 2 Bath
  • $2,725

Charming 2/2 House in New Town - Lovely single-family home, 2-bedroom, 2-bath with large fenced-in yard features eat-in kitchen, AC, washer/dryer and off-street parking. Pets considered. Available early January $2,725/mo + water & electric. First/Last and Security Deposit required. (RLNE3198800) Amenities Small Dogs Allowed Cats Allowed Air Conditioning Other - sf, w/d. dw Yard Patio

Showing records 1 to 24 of 28

Apartment Rental Statistics Key West, FL

Rental Type Active
Listings
Minimum
Rent
Maximum
Rent
Average
Rent
Studio 2 $1,750 $3,835 $2,792
1 Bedroom 5 $1,725 $6,135 $4,011
2 Bedroom 17 $2,425 $8,135 $5,099
3 Bedroom 4 $3,000 $12,135 $6,442
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