$2,500 per month
- 2,244 Sq Ft
- Property for Rent
2001 Flagler Ave, Key West, FL 33040
2001 Flagler Ave, Key West, FL 33040
50
Homes for Rent in ZIP Code 33040
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$5,750 per month
- 3 Beds
- 3 Baths
- 1,380 Sq Ft
- Property for Rent
59 Palm Dr, Key West, FL 33040
59 Palm Dr, Key West, FL 33040 -
$7,500 per month
- 3 Beds
- 2 Baths
- Property for Rent
18 W Circle Dr, Key West, FL 33040
18 W Circle Dr, Key West, FL 33040 -
$2,508 - $4,443 per month
3900 S Roosevelt Blvd, Key West, FL 33040Ocean Walk
Studio - 3 Beds
3900 S Roosevelt Blvd, Key West, FL 33040
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$5,200 per month
- 3 Beds
- 2 Baths
- 1,500 Sq Ft
- Property for Rent
3708 Cindy Ave, Key West, FL 33040
3708 Cindy Ave, Key West, FL 33040Welcome to 3708 Cindy Avenue, a beautifully renovated and well-maintained three-bedroom, two-bathroom home in New Town, Key West. The open floor plan connects a sleek, updated kitchen with stainless steel appliances to bright living spaces that transition easily from everyday living to entertaining.The spacious primary suite includes a modern bathroom and walk-in closet, while two additional
Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty
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$2,854 - $3,424 per month
750 Fort St, Key West, FL 33040Lofts at Bahama Village
1 - 3 Beds
750 Fort St, Key West, FL 33040
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$3,800 per month
- 3 Beds
- 2 Baths
- 1,700 Sq Ft
- Property for Rent
625 Overseas Hwy, Key West, FL 33040
625 Overseas Hwy, Key West, FL 33040Waterfront, three bed, two bath apartment with seawall and space to float your boat right out back (up to 21 ft) on a canal! Roomy interior living space is over 1700 sq ft. One side faces the canal leading out into the 'Back Country'. the other side faces US Hwy 1. Tile floors throughout with newer appliances including full sized washer & dryer. Available for 6 to 12 months. Three assigned
Walt Lee Berkshire Hathaway HomeServices Knight & Gardner Realty
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$2,853 - $3,969 per month
10 Betty Rose Dr, Key West, FL 33040The Quarry
1 - 3 Beds
10 Betty Rose Dr, 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
1207 William St Unit 3, Key West, FL 33040Step 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
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$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
1505 White St Unit Two bedroom, Key West, FL 33040This 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
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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
709 Emma St Unit 1, Key West, FL 33040Tropical 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
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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
1901 S Roosevelt Blvd Unit 404N, Key West, FL 33040This 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
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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
1220 Newton St Unit 2, Key West, FL 33040This 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
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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
2418 Linda Ave, Key West, FL 33040House 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
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$2,100 per month
- 1 Bed
- 1 Bath
- 754 Sq Ft
- Condo for Rent
2601 S Roosevelt Blvd, Key West, FL 33040
2601 S Roosevelt Blvd, Key West, FL 33040100% 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
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$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 Unit 302A, Key West, FL 330401800 Atlantic blvd. Has so much to offer, quiet location, fantastic apartment views, and a long list of amenities.
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$6,750 per month
- 3 Beds
- 2 Baths
- 1,304 Sq Ft
- Property for Rent
1422 Boca Chica Rd, Key West, FL 33040
1422 Boca Chica Rd, Key West, FL 33040Turnkey Furnished Rental - Annual, Seasonal, or Monthly Options AvailableThis rare and exceptional waterfront home is offered fully furnished--including kitchenware, linens, and curated art--ready for move-in 11/1. Available annually at $6,750/month (tenant pays only electric), or as a monthly/seasonal vacation rental (inquire for rates).This elevated 3-bedroom, 2-bath split-floorplan home
Michelle Blades Realty Executives Florida Keys Old Town
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$2,500 per month
- 2 Beds
- 1 Bath
- 560 Sq Ft
- Condo for Rent
1209 William St Unit 1, Key West, FL 33040
1209 William St Unit 1, Key West, FL 33040This 2/1 Old Town apartment is in good condition with a new shower and combination window and ductless a/c units. Stack laundry in the unit and 1 off street parking spot included. Available August 1st. F/L/S to move in. Please contact David Austin, Anchor Line Realty, Licensed Real Estate Broker for showings.
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$3,000 per month
- 2 Beds
- 2 Baths
- 804 Sq Ft
- Property for Rent
3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040
3930 S Roosevelt Blvd Unit 109N, Key West, FL 33040AVAILABLE 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
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$4,000 per month
- 2 Beds
- 2.5 Baths
- 842 Sq Ft
- Townhouse for Rent
63 Seaside Ct N, Key West, FL 33040
63 Seaside Ct N, Key West, FL 33040Seaside Key West Residents is a fully gated Community divided in two sections. This townhouse has the feel of tropical living and add to that a garage with storage, rear yard, a clubhouse, gym and a pool for each side. Manager on site, security gate/cameras provide privacy with the Atlantic Ocean just across S. Roosevelt Boulevard. Sturdy concrete construction, impact resistant windows &
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$3,450 per month
- 2 Beds
- 2 Baths
- Property for Rent
726 Eaton St, Key West, FL 33040
726 Eaton St, Key West, FL 33040Step 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
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$4,500 per month
- 2 Beds
- 2 Baths
- 772 Sq Ft
- Condo for Rent
3675 Seaside Dr Unit 434, Key West, FL 33040
3675 Seaside Dr Unit 434, Key West, FL 33040This newly-renovated, bright and airy 4th-floor unit boasts poolside views from the private balcony. The open living area flows seamlessly into the kitchen which includes granite countertops, stainless steel appliances, and custom wood cabinetry. Both bedrooms feature spacious en-suite bathrooms, and the large primary suite has a walk-in closet. This condo includes a covered parking space
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$2,000 per month
- 1 Bath
- Property for Rent
5555 College Rd Unit 10, Key West, FL 33040
5555 College Rd Unit 10, Key West, FL 33040Lived Aboard Slip For Rent!!!! The Total Keys Living!!****SeaPen Included in Price!!!***This 40' slip on Conch Pier can accommodate a total vessel length of 45'' and offers state-of-the-art floating docks. This slip is equipped with a brand new SeaPen boat lift. This lift will keep your boat out of the water when you are not using it. Sunset Marina has every amenity imaginal and is located on
Bobby Coe RE/MAX Keys Connection (KW)
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$3,600 - $3,800 per month
5555 College Rd, Key West, FL 33040Sunset Marina Apts
2 Beds
5555 College Rd, Key West, FL 33040
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$3,200 per month
- 1 Bed
- 1 Bath
- 536 Sq Ft
- Property for Rent
201 Coppitt Rd Unit 102, Key West, FL 33040
201 Coppitt Rd Unit 102, Key West, FL 33040Waterfront ground-floor one-bedroom, one-bath condominium available for immediate 12-month lease. This well-maintained unit features central A/C, ceramic tile flooring, an in-unit washer and dryer, and a spacious bedroom with a large closet. Enjoy a private balcony with water views and easy access for kayaking. One assigned parking space included. Located just minutes from Key West and NAS.Rent
Megan Mcdowell eXp Realty LLC
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$14,205 per month
- 2 Beds
- 2 Baths
- 2,023 Sq Ft
- Condo for Rent
536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040
536 Fleming St Unit FL2-ID1297611P, Key West, FL 33040Experience 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
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$4,800 per month
- 3 Beds
- 2 Baths
- 1,152 Sq Ft
- Property for Rent
844 Olivia St, Key West, FL 33040
844 Olivia St, Key West, FL 33040AVAILABLE 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
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$8,250 per month
- 2 Beds
- 2.5 Baths
- 796 Sq Ft
- Condo for Rent
524 Porter Ln Unit ID1297831P, Key West, FL 33040
524 Porter Ln Unit ID1297831P, Key West, FL 33040Conveniently 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
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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
1608 Venetian Dr, Key West, FL 33040Ground 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)
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$8,697 per month
- 3 Beds
- 2 Baths
- 1,399 Sq Ft
- Condo for Rent
2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040
2026 Seidenberg Ave Unit ID1297830P, Key West, FL 33040Welcome 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,
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$7,000 per month
- 4 Beds
- 2 Baths
- Property for Rent
417 Southard St Unit A, Key West, FL 33040
417 Southard St Unit A, Key West, FL 33040Long 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
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$9,672 per month
- 3 Beds
- 2 Baths
- 893 Sq Ft
- Condo for Rent
1130 Duval St Unit ID1297835P, Key West, FL 33040
1130 Duval St Unit ID1297835P, Key West, FL 33040Beautiful 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,
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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
6440 2nd St Unit 9, Key West, FL 33040Half 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)
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$7,962 per month
- 3 Beds
- 3 Baths
- 2,518 Sq Ft
- Condo for Rent
8 Floral Ave Unit ID1297832P, Key West, FL 33040
8 Floral Ave Unit ID1297832P, Key West, FL 33040The 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
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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
1623 Venetian Dr, Key West, FL 33040WATERFRONT!! 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
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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
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
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$13,000 per month
- 4 Beds
- 4 Baths
- Property for Rent
2214 Seidenberg Ave, Key West, FL 33040
2214 Seidenberg Ave, Key West, FL 33040Welcome 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.
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$17,010 per month
- 2 Beds
- 3 Baths
- 1,345 Sq Ft
- Condo for Rent
629 Elizabeth St Unit ID1297833P, Key West, FL 33040
629 Elizabeth St Unit ID1297833P, Key West, FL 33040Casa 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
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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
710 Caroline St, Key West, FL 33040This 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
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$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
1315 Whitehead St Unit ID1297834P, Key West, FL 33040Southernmost 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
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