Homes for Rent near May Sands Montessori School

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  $1,300 per month

  • 154 Sq Ft
  • Property for Rent

  302 Southard St Unit 206A, Key West, FL 33040

  Office unit available for rent at the Courthouse Business Center. This is a professional only building, no retail / service building. Many people in the office building are lawyers Very quiet office space, with a parking lot in the center of Old Town, and conference room. Available October 1st.

  

  Everett Watkins

  Keller Williams Key West Compass Realty

  (786) 686-1404

  302 Southard St Unit 206A, Key West, FL 33040
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  Explore May Sands Montessori School

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  /5

  $2,500 per month

  • 2,244 Sq Ft
  • Property for Rent

  2001 Flagler Ave, Key West, FL 33040

  Prime 2,244 SQFT Vacant Lot Available for Rent.A rare opportunity to lease a centrally located vacant lot in the heart of New Town! Whether you're looking to advertise your business, operate a food truck, start a new venture, or create a space uniquely your own--this versatile lot offers endless potential. Multiple possible uses (tenant to verify).Please do not walk the property without prior

  

  Everett Watkins

  Keller Williams Key West Compass Realty

  (786) 244-5194

  2001 Flagler Ave, Key West, FL 33040
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  /35

  $2,854 - $3,961 per month

  Lofts at Bahama Village

  1 - 3 Beds

  750 Fort St, Key West, FL 33040

  Discover your place in the heart of Key West's most historic and vibrant neighborhood. The Lofts at Bahama Village offers affordable housing options designed for locals, where homeownership and rental opportunities meet the warmth of a close-knit community.Live steps away from iconic Key West landmarks, while enjoying the charm and cultural heritage that make Bahama Village truly one of a

  750 Fort St, Key West, FL 33040
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  $5,000 per month

  • 3 Beds
  • 3 Baths
  • 1,216 Sq Ft
  • Property for Rent

  1207 William St Unit 3, Key West, FL 33040

  Step inside this exceptional 3-bedroom condo, where modern living meets unmatched versatility. Each of the three bedrooms features its own en-suite bathroom, ensuring comfort and privacy for all. But the true standout feature? Three separate entrances, with two bedrooms featuring private exterior access. There is a door in the hallway that can be closed to separate the front and back of the house

  Sarah Bixby eXp Realty LLC

  1207 William St Unit 3, Key West, FL 33040
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  $2,614 - $4,501 per month

  Ocean Walk

  Studio - 3 Beds

  3900 S Roosevelt Blvd, Key West, FL 33040

  Ocean Walk apartments are located on the peaceful Atlantic side of the island, nestled among lush natural vegetation, just steps away from the beach. Ideally located just minutes from the best dining, shopping and entertainment Key West has to offer, Ocean Walk Apartment Homes boast spacious one, two, and three bedroom apartments, spectacular views, and first-rate amenities. Each recently

  3900 S Roosevelt Blvd, Key West, FL 33040
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  $3,300 per month

  • 1 Bed
  • 1 Bath
  • 416 Sq Ft
  • House for Rent

  709 Emma St Unit 1, Key West, FL 33040

  Tropical and Islandy Bungalow Style Home In KEY WEST!! Cute As A Button! 1 Bedroom 1 Full Bath, Furnished, Very Modern, Remodeled, Single Family Home. Located In Old Town/Downtown Area. 3 Blocks From Duval St., Yet Far Enough Away To Enjoy Your Private, Quiet Lifestyle. Property Is Fenced. Large Front Porch, Spacious Side Yard For Entertaining. Assigned Off Street Parking. Central Air. Electric,

  Sabrina Liguori Premium Properties Real Estate

  709 Emma St Unit 1, Key West, FL 33040
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  /18

  $3,900 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  1505 White St Unit Two bedroom, Key West, FL 33040

  This property at 1505 White two bedrooms and one bathroom, encompassing a total of over 1000 square feet. With over 700 sq ft of outdoor living The unit comes furnished and includes air conditioning for climate control. The smoke-free environment ensures a healthy living space. Exterior amenities include a gated entry for added security, a grill for outdoor cooking, and a deck for relaxation or

  1505 White St Unit Two bedroom, Key West, FL 33040
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  $2,800 per month

  • 1 Bed
  • 1 Bath
  • 394 Sq Ft
  • Apartment for Rent

  1220 Newton St Unit 2, Key West, FL 33040

  This is a one bedroom, sweet apartment with a loft upstairs. washer and dryer, dishwasher. Good size living room with large windows with great light. Seperate bedroom, with bath off the bedroom. Perfect for couple. pets welcome with approval. Available October 1

  Susan Rich Select Properties of NWFL

  1220 Newton St Unit 2, Key West, FL 33040
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  $3,200 per month

  • 2 Beds
  • 2 Baths
  • 1,175 Sq Ft
  • Condo for Rent

  1901 S Roosevelt Blvd Unit 404N, Key West, FL 33040

  This 2 bedroom, 2 bath fully furnished condo at La Brisa condominium is available for rent October 1, 2025 through December 27, 2025. Reduced rent is $3,200 per month and includes $200 per month for water/sewer and electric. Wi-Fi also included. There's a covered parking space and adjacent storage space. Sorry, no pets and a background check is required. Exit cleaning fee of $250. La Brisa

  1901 S Roosevelt Blvd Unit 404N, Key West, FL 33040
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  /10

  $2,100 per month

  • 1 Bed
  • 1 Bath
  • 754 Sq Ft
  • Condo for Rent

  2601 S Roosevelt Blvd, Key West, FL 33040

  100% Application before tour.Available: Oct 3rdPet Allowed.Discover your perfect Key West retreat! This cozy 754 sq ft condo at 2601 S Roosevelt Blvd offers a comfortable and efficient layout with one bedroom and one full bathroom. Perfectly sized for easy living, it's an ideal lock-and-leave option just moments from the beach and vibrant downtown. Enjoy the incredible convenience

  Sandra Leufkens

  2601 S Roosevelt Blvd, Key West, FL 33040
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  $5,500 per month

  • 3 Beds
  • 2 Baths
  • 1,613 Sq Ft
  • House for Rent

  2418 Linda Ave, Key West, FL 33040

  House For Rent - 3/2 $5500/Month (Could Also Be 4/2) - 1 Year Lease (Possible Future Renewals) - Mid Town Key West - Unfurnished - Utilities Not Included - Saltwater Pool - Access To Salt Ponds - Laundry On-Site - F&S Required For Move-In - No Pets Allowed - No Subleasing - No Smoking In Home - Background Check Required - Renters Insurance Required

  2418 Linda Ave, Key West, FL 33040
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  $2,750 per month

  • 2 Beds
  • 2 Baths
  • 804 Sq Ft
  • Property for Rent

  3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040

  AVAILABLE NOW!! Las Salinas condominium. Two bedrooms and two baths located on the first floor. Its private balcony overlooks the pool.Las Salinas is located on South Roosevelt Blvd across the street from the oceanfront boardwalk perfect for biking, jogging and walking as it curves along the coastline toward Smathers Beach. This unit comes with its own private storage room. In addition to the

  Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

  3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040
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  /14

  $5,500 per month

  • 2 Beds
  • 2 Baths
  • 1,200 Sq Ft
  • Condo for Rent

  1800 Atlantic Blvd Unit 302A, Key West, FL 33040

  1800 Atlantic blvd. Has so much to offer, quiet location, fantastic apartment views, and a long list of amenities.

  1800 Atlantic Blvd Unit 302A, Key West, FL 33040
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  $3,450 per month

  • 2 Beds
  • 2 Baths
  • Property for Rent

  726 Eaton St, Key West, FL 33040

  Step into Key West history with this beautifully updated two-bedroom, two-bathroom first-floor home tucked away behind the serene Freeman-Curry House, circa 1865, on Eaton Street. The Carriage House offers a quiet, private retreat while in the heart of Old Town.This apartment features two spacious bedrooms and two full bathrooms and includes a washer and dryer, refrigerator, dishwasher, built-in

  Megan Mcdowell eXp Realty LLC

  726 Eaton St, Key West, FL 33040
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  /18

  $3,600 - $3,800 per month

  Sunset Marina Apts

  2 Beds

  5555 College Rd, Key West, FL 33040

  5555 College Rd, Key West, FL 33040
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  /14

  $4,800 per month

  • 3 Beds
  • 2 Baths
  • 1,152 Sq Ft
  • Property for Rent

  844 Olivia St, Key West, FL 33040

  AVAILABLE SEPTEMBER 1,2025 3 bedroom 2 bathroom in Old Town Key West with off street parking. Make an appointment to view this home and see all the possibilities this home has to offer. First room can be a bedroom or living area. Back room is a washer dryer room, it also has a small bathroom and shower. Upstairs loft is a great room for a bedroom along with seating area or bedroom and office, one

  Rebecca Cobo Berkshire Hathaway HomeServices Knight & Gardner Realty

  844 Olivia St, Key West, FL 33040
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  /20

  $17,010 per month

  • 2 Beds
  • 3 Baths
  • 1,345 Sq Ft
  • Condo for Rent

  629 Elizabeth St Unit ID1297833P, Key West, FL 33040

  Casa Azul is a luxurious modern cottage featuring an open-concept living area that is bathed in natural sunlight. Enjoy a dip in the heated saltwater plunge pool with a waterfall feature and night lighting. Located in Old Town Key West, just two blocks from Duval Street, this pet-friendly home offers private parking and is perfect for your next extended stay.Casa Azul perfectly blends comfort

  629 Elizabeth St Unit ID1297833P, Key West, FL 33040
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  $4,000 per month

  • 4 Beds
  • 2 Baths
  • 1,593 Sq Ft
  • Property for Rent

  1608 Venetian Dr, Key West, FL 33040

  Ground level single family home with living room, dining area, new kitchen and appliances, four bedrooms, two new baths, laundry room, central AC, tile floors, in Key West's New Town. Available for a yearly lease. Would consider rent-to-own offers at sales price of $995,000.

  Dave Lewis Key West Real Estate Sales & Rentals, LLC (KW)

  1608 Venetian Dr, Key West, FL 33040
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  /20

  $10,501 per month

  • 3 Beds
  • 2 Baths
  • 893 Sq Ft
  • Condo for Rent

  1130 Duval St Unit ID1297835P, Key West, FL 33040

  Beautiful 3-bedroom, 2-bath monthly rental located on Key West's famous Duval Street. Guests enjoy easy access to shopping, dining, and entertainment options. The Green Pineapple offers charming architecture and an authentic taste of Key West’s unique culture and lifestyle. Visit The Green Pineapple storefront for a refreshing wellness journey. Discover a curated selection of nourishing foods,

  1130 Duval St Unit ID1297835P, Key West, FL 33040
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  $7,000 per month

  • 4 Beds
  • 2 Baths
  • Property for Rent

  417 Southard St Unit A, Key West, FL 33040

  Long term rental, 4 bedroom, 2-bathroom furnished apartment is conveniently located just steps away from Duval Street, Mile Marker 0, and within walking distance to the Southernmost Point, Fort Zachary Taylor Historic State Park. The apartment boasts Beautiful bathrooms with walk-in showers, spacious kitchens equipped with upgraded stainless steel appliances, a stunning waterfall kitchen counter

  Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty

  417 Southard St Unit A, Key West, FL 33040
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  /20

  $15,705 per month

  • 2 Beds
  • 2 Baths
  • 2,023 Sq Ft
  • Condo for Rent

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040

  Experience the allure of this luxurious 2,000+ square foot penthouse, The Maloney, which occupies the entire second story of a historic red brick building at the corner of Fleming and Simonton. Originally constructed in 1908 as Key West's first pharmacy, this building now features two penthouse units and a first-floor boutique. The Maloney is available exclusively for monthly rentals, requiring a

  536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
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  $2,800 per month

  • 2 Beds
  • 1 Bath
  • 620 Sq Ft
  • Property for Rent

  6440 2nd St Unit 9, Key West, FL 33040

  Half of a Duplex, unfurnished, tenant pays for all utilities, instant on demand tankless water heater saves on your electric bill. Approx. 600 Sq.Ft. 2 units per building so only 1 shared wall for a typical duplex layout with fenced gravel yard, landscaping with palm trees. Has hookups for a clothes washing machine or the new combination models that wash and dry in the same drum. Kitchen has a

  Dave Lewis Key West Real Estate Sales & Rentals, LLC (KW)

  6440 2nd St Unit 9, Key West, FL 33040
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  /20

  $8,575 per month

  • 3 Beds
  • 2 Baths
  • 1,399 Sq Ft
  • Condo for Rent

  2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040

  Welcome to Hidden Oasis, a luxurious three-bedroom, two-bathroom home nestled in the heart of Midtown, Key West. This stunning property offers contemporary luxury with an open floor plan, situated on a private fenced-in yard on a corner lot with lush tropical landscaping. Feel at home as you step through French doors to the backyard, featuring a private heated pool, lounge seating, a TV, a grill,

  2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040
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  $12,000 per month

  • 3 Beds
  • 2.5 Baths
  • 2,400 Sq Ft
  • House for Rent

  1623 Venetian Dr, Key West, FL 33040

  WATERFRONT!! EXITS TO THE OCEAN. FULLY FURNISHED HOME, READY TO MOVE IN. ONE OF THE FEW CANALS LEADING TO OCEAN INSIDE KEY WEST.Completely remodeled Oceanfront 3 bedrooms, 2 bathrooms, 2 car garage, completely furnished dream home on the water with game room and a 50ft dock on a very private neighborhood. This home is move in ready. UPSTAIRS- This home has a brand new top of the line kitchen with

  Esney Diaz Premier Real Estate Associates

  1623 Venetian Dr, Key West, FL 33040
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  /20

  $21,600 per month

  • 4 Beds
  • 3.5 Baths
  • 1,797 Sq Ft
  • Condo for Rent

  1315 Whitehead St Unit ID1297834P, Key West, FL 33040

  Southernmost View is a modern and luxurious waterfront home located in a private seven-home gated community, just steps from the beach and the Southernmost Point of the continental USA. Enjoy turquoise blue waters from the rooftop sundeck, perfect for tanning, reading, and sipping your morning coffee. Relax under the southernmost stars or watch the sunset over the horizon.This upscale beach

  1315 Whitehead St Unit ID1297834P, Key West, FL 33040
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  $13,000 per month

  • 4 Beds
  • 4 Baths
  • Property for Rent

  2214 Seidenberg Ave, Key West, FL 33040

  Welcome to your luxurious oasis in Key West, where modern comfort meets tropical paradise. This stunning new construction home features four spacious bedrooms, each with an en suite bathroom. Lushly landscaped grounds, this 5,700 square foot property offers plenty of room to unwind and enjoy the beauty of the island.Imagine starting your day with a refreshing swim in the large, private, heated

  Paige Bethel Island Home Realty Inc.

  2214 Seidenberg Ave, Key West, FL 33040
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  /20

  $7,972 per month

  • 3 Beds
  • 3 Baths
  • 2,518 Sq Ft
  • Condo for Rent

  8 Floral Ave Unit ID1297832P, Key West, FL 33040

  The Haven House is a truly heavenly retreat nestled on the quiet residential canals in Key Haven. This home boasts a modern waterfront private backyard with a dock and boat lift. With space-maximizing and luxury island touches from top to bottom, this monthly rental has it all. Stay just 15 minutes from downtown Duval Street in this one-of-a-kind island home.Seamless indoor-outdoor

  8 Floral Ave Unit ID1297832P, Key West, FL 33040
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  $14,000 per month

  • 4 Beds
  • 4.5 Baths
  • 2,250 Sq Ft
  • House for Rent

  710 Caroline St, Key West, FL 33040

  This magnificent, historic, turn-key home is located on infamous Caroline Street, just a few blocks from Duval Street in the Historic Seaport area, making it one of the most ideal locations in Key West. The property underwent a multi-year complete renovation culminating in 2023, including being raised appx. 5 feet and impact glass windows & doors. The 2,250-square-foot home features a stunning

  jesse friedman Real Broker, LLC

  710 Caroline St, Key West, FL 33040
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  /20

  $6,641 per month

  • 2 Beds
  • 2.5 Baths
  • 796 Sq Ft
  • Condo for Rent

  524 Porter Ln Unit ID1297831P, Key West, FL 33040

  Conveniently situated in the picturesque Truman Annex gated community, this charming 2-bedroom, 2.5-bath apartment is perfect for your next island getaway. This storybook corner unit features two private balconies off each bedroom and a back deck equipped with all your outdoor dining necessities. Close enough to everything, yet just far enough away, this apartment allows you to feel at home while

  524 Porter Ln Unit ID1297831P, Key West, FL 33040
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  $5,082 per month

  • 1 Bed
  • 1 Bath
  • 419 Sq Ft
  • Condo for Rent

  817 Terry Ln Unit ID1297837P, Key West, FL 33040

  "Lil Bit" is a rare find in the historic Bahama Village neighborhood. This classic "conch" home is modern and renovated to have an elevated feel but retains the charm and character of old Key West. Perfect for a couple or visitors looking for a monthly stay, this home is equipped with everything you need. While it is a "Lil Bit," the space feels large, open, and fresh, and is a short walk to Fort

  817 Terry Ln Unit ID1297837P, Key West, FL 33040
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  $2,900 per month

  • 2 Beds
  • 2 Baths
  • 804 Sq Ft
  • Condo for Rent

  3930 S Roosevelt Blvd Unit N109, Key West, FL 33040

  AVAILABLE NOW!! Las Salinas condominium. Two bedrooms and two baths located on the first floor. Its private balcony overlooks the pool. Las Salinas is located on South Roosevelt Blvd across the street from the oceanfront boardwalk perfect for biking, jogging and walking as it curves along the coastline toward Smathers Beach. This unit comes with its own private storage room. In addition to the

  3930 S Roosevelt Blvd Unit N109, Key West, FL 33040
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  $2,500 per month

  • 1 Bed
  • 1 Bath
  • 400 Sq Ft
  • House for Rent

  6400 2nd St, Key West, FL 33040

  Very nice bright airy updated and freshly painted, central AC, fans, tiled floor throughout, private large yard, walls. Covered porch.Utilities included excluding internet and cable. No smoking. 2 people maximum.

  6400 2nd St, Key West, FL 33040
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  $4,700 per month

  • 2 Beds
  • 1.5 Baths
  • 850 Sq Ft
  • House for Rent

  2005 Fogarty Ave, Key West, FL 33040

  PRICE REDUCED! This Quintessential “Keysie” home is truly something special. Situated in a quiet, family friendly, local neighborhood, this Cozy 2 bedroom, 1 bath “plus”, includes an additional private outdoor shower in a tropical setting! FULLY furnished/turn key with all living essentials, complete renovation in Spring 2025. Includes laundry room as well as large tranquil backyard with lush

  2005 Fogarty Ave, Key West, FL 33040
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  $4,000 per month

  • 2 Beds
  • 1.5 Baths
  • 800 Sq Ft
  • House for Rent

  6800 Maloney Ave, Key West, FL 33040

  Property Id: 1805361Rare opportunity to rent an oceanfront house for long term rental w/in the 1st 5 miles of Key West w/ seawall for boat or just enjoy the view! 2 & 2. $4,000/ month for 12 month lease + electric, water & internet. Includes sewer, trash, basic cable & landscaping. 1st, last & $2500 deposit. Available Aug. 1. Mostly unfurnished. 1 bedroom comes w/ murphy bed w/ ocean view

  6800 Maloney Ave, Key West, FL 33040
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  $5,500 per month

  • 3 Beds
  • 3 Baths
  • 1,600 Sq Ft
  • House for Rent

  56 Golf Club Dr, Key West, FL 33040

  Property Id: 18076993 bedroom, 2.5 bath home for rent starting Seltember 1. Will consider a lease for 5 months ranging to to 17 months (lease amount may vary by term)Everyone tells us they feel right at home there. Beautiful setting in a quiet neighborhood. Close to all that Key West offers. We may consider a small dog.

  56 Golf Club Dr, Key West, FL 33040
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  /14

  $4,000 per month

  • 2 Beds
  • 1 Bath
  • 1,000 Sq Ft
  • Condo for Rent

  1406 S Roosevelt Blvd, Key West, FL 33040

  This charming home features:A spacious open floor plan with plenty of natural lightLarge yard perfect for relaxing or entertainingBack deck (currently being installed) for outdoor livingLots of storage Off-street parking for convenienceUtilities includedLocated in a highly desired area of Key West, just minutes from the beach for morning strolls or afternoon fun.No

  1406 S Roosevelt Blvd, Key West, FL 33040
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  /20

  $5,800 per month

  • 3 Beds
  • 3 Baths
  • 2,109 Sq Ft
  • Condo for Rent

  1500 Atlantic Blvd Unit 208, Key West, FL 33040

  Your peaceful, private and perfectly Key West rental awaits you! Key West Beach Club Enjoy waterfront living in this spacious 3 Bedroom / 3 Bathroom condo that blends comfort with resort-style amenities. The setting is magical, serene, and beautifully peaceful—perfect for a Key West lifestyle.Features & Amenities:Gated community with two sparkling poolsFitness center, sauna,

  1500 Atlantic Blvd Unit 208, Key West, FL 33040
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  $3,000 per month

  • 2 Beds
  • 1 Bath
  • 700 Sq Ft
  • Condo for Rent

  1504 Flagler Ave Unit 1#, Key West, FL 33040

  We are family oriented here at this property; we make our tenants feel at home like family. Available 24/7.Partners allowed. Two single roommates. Pets allowed with deposit and referral letter from vet - shots are up to date. One on-property parking spot allowed per unit. Smoke free property.

  1504 Flagler Ave Unit 1#, Key West, FL 33040
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  /13

  $3,950 per month

  • 2 Beds
  • 1 Bath
  • 750 Sq Ft
  • Condo for Rent

  1209 Pearl St Unit Down, Key West, FL 33040

  Clean furnished downstairs apt near Bayview Park in Key West. One BR is furnished, 2nd room can be used as an office or as 2nd BR. Additional outdoor shower, fenced, landscaped, and very private. Rent includes All utilities! NO Pets or animals and NO Smoking! Private laundry and off street parking! Perfect for single professional or Military.6 mo lease plus. Call Mark for more details

  1209 Pearl St Unit Down, Key West, FL 33040
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  $2,100 per month

  • Studio
  • 1 Bath
  • 252 Sq Ft
  • Condo for Rent

  908 Elizabeth St Unit 4, Key West, FL 33040

  Very cute little garden studio available Early August. Small but in the very HEART of it all! Walk to everything Old Town has to offer! Tenant pays electric and cable/internet. F/S/S. Sorry No Pets!

  908 Elizabeth St Unit 4, Key West, FL 33040

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