$6,000 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
67
Homes for Rent near Key West High School
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$1,000 per month
- 1 Bed
- 367 Sq Ft
- Property for Rent
600 Whitehead St Unit C-4, Key West, FL 33040
600 Whitehead St Unit C-4, Key West, FL 33040 -
$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 -
$2,750 - $3,784 per month
3333 Duck Ave, Key West, FL 33040Arrive Key West
1-2 Beds
3333 Duck Ave, Key West, FL 33040
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$3,650 per month
- 3 Beds
- 2 Baths
- 1,285 Sq Ft
- House for Rent
3717 Palmetto St, Big Pine Key, FL 33043
3717 Palmetto St, Big Pine Key, FL 33043Nice remote 3/2 in the heart of big pine key with a canal in the back where you would be able to dock your boat; beautiful location, a relaxing getaway, close to the open water, less than an hour away from Key West, minutes away from shopping, schools, and park. Call Now. Background and Credit Report (we will provide you with a link, and your customer will pay for the fee), Proof of employment,
George Assal ASLO Real Estate
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$2,314 - $4,694 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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$4,000 per month
- 2 Beds
- 1 Bath
- 840 Sq Ft
- House for Rent
29955 Ocean Ln, Big Pine Key, FL 33043
29955 Ocean Ln, Big Pine Key, FL 33043Beautifully redone 2 bedroom, 1 bath home with an acre of land for all of your storage needs. Boats, RV's and trailers will all fit. This home is very open and bright! The patio that leads into the master bedroom and living room is perfect for entertaining and extra space.
Casey Elliott Key Colony Beach Realty
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$2,606 - $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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$3,950 per month
- 2 Beds
- 3 Baths
- 1,100 Sq Ft
- Property for Rent
31111 Hibiscus Dr Unit lot 31, Big Pine Key, FL 33043
31111 Hibiscus Dr Unit lot 31, Big Pine Key, FL 33043Come live the island life in this immaculately kept 2 bedroom 3 full bath with additional room on ground floor.If you love nature Big Pine is for you. Close enough to enjoy both Marathon and Key West for the nights where you want to see the local action but far enough away for peace and tranquility. Home sits on a spacious 60 ft of canal front lot with quick access to Gulf or Atlantic from Bogie
Kimberley Frazier Keller Williams Key West Compass Realty
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$3,950 - $4,200 per month
28501 Channel View Dr, Little Torch Key, FL 33042Little Torch Cottages
2 Beds
28501 Channel View Dr, Little Torch Key, FL 33042
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$6,000 per month
- 3 Beds
- 2 Baths
- 1,800 Sq Ft
- House for Rent
1655 Sunrise Dr, Big Pine Key, FL 33043
1655 Sunrise Dr, Big Pine Key, FL 33043Your clients will love having their morning coffee in the family room and watching the Sun rise over No Name Key.This back yard pool is completely private and perfect for family and guests. Sit in the Tiki Bar, sip a Margarita and enjoy the ocean and pool views. The tropical trees and setting will make you feel like you are living at a Caribbean Resort. Dock you boat at the cut-in boat slip, and
Mark Peterson
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$3,600 per month
5555 College Rd, Key West, FL 33040Sunset Marina Apts
2 Beds
5555 College Rd, Key West, FL 33040
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$5,000 per month
- 3 Beds
- 1 Bath
- 1,116 Sq Ft
- House for Rent
27316 Cayman Ln Unit 1, Summerland Key, FL 33042
27316 Cayman Ln Unit 1, Summerland Key, FL 33042Presenting Villa Marquesa — the perfect opportunity to lease a charming private villa in the heart of Ramrod Key, located in the picturesque Lower Keys. This fully furnished 3-bedroom, 1-bath tropical retreat offers stylish South Florida beach decor, a fully equipped kitchen, and two spacious living areas for ultimate comfort. Ideal for tenants seeking privacy, relaxation, and a resort-style
Gilbert Garcia Proxy Realty Group LLC
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$3,200 per month
- 1 Bed
- 1 Bath
- 536 Sq Ft
- Condo for Rent
201 Coppitt Rd Unit 102B, Key West, FL 33040
201 Coppitt Rd Unit 102B, Key West, FL 33040Property Id: 1764681Available August 1, 2025 - Enjoy peaceful waterfront living in this beautifully updated, unfurnished ground-floor 1BR/1BA condo located in a quiet community on Big Coppitt Key, just minutes from Key West. This charming home features a remodeled bathroom, in-unit washer and dryer, and designated parking. All utilities—water, electric, trash, and lawn care—are included
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$5,000 per month
- 2 Beds
- 2 Baths
- 1,000 Sq Ft
- Property for Rent
417 Southard St Unit B, Key West, FL 33040
417 Southard St Unit B, Key West, FL 33040This 2-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 with seating,
Tammy Stiles Berkshire Hathaway HomeServices Knight & Gardner Realty
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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
6800 Maloney Ave, Key West, FL 33040Property 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
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$5,000 per month
- 3 Beds
- 2 Baths
- House for Rent
3635 Tradewinds St, Big Pine Key, FL 33043
3635 Tradewinds St, Big Pine Key, FL 33043Beautiful Waterfront Home for Rent in the Florida Keys - Boater's Paradise!Ready to move in! This stunning 3-bedroom, 2-bathroom home is perfect for boat lovers and anyone seeking the ultimate Keys lifestyle. Located on a peaceful canal with direct access to open water, this home offers the ideal setting for fishing, boating, and relaxing walks.Property Features:3 spacious bedrooms, 2 full
Michel Luna Lifestyle International Realty
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$1,500 per month
- 1 Bed
- 1 Bath
- House for Rent
2102 Staples Ave, Key West, FL 33040
2102 Staples Ave, Key West, FL 33040Property Id: 1785777Key West, FL (Midtown) - available July 1Private furnished bedroom and bathroom with private entrance for rent for a single person. Room comes furnished including tv, microwave, refrigerator and window AC. Walking distance to the beach. Ready to move in.$1500 per month - utilities and wi-fi included. 6-month lease. First month's rent ($1500),
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$4,000 per month
- 2 Beds
- 2 Baths
- 1,258 Sq Ft
- Property for Rent
29487 Ranger Ave, Big Pine Key, FL 33043
29487 Ranger Ave, Big Pine Key, FL 33043Unfurnished canal-front 2 bed, 2 bath home in a quiet neighborhood, just minutes from shopping, restaurants, marina, bait shop, and local parks. Enjoy fantastic boating with easy access to both the ocean and backcountry--bring your boat!Home features an open layout, primary bedroom with ensuite bath, laundry closet, and a covered screened porch. The fully fenced yard offers plenty of space for
Melissa Gibbins Expert Realty LLC (HQ)
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$4,990 per month
- 3 Beds
- 3 Baths
- 1,600 Sq Ft
- House for Rent
56 Golf Club Dr, Key West, FL 33040
56 Golf Club Dr, Key West, FL 33040Property Id: 18076993 bedroom, 2.5 bath home for rent starting August 1. Will consider a lease for 5 months ranging to to 17 months. 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.
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$5,000 per month
- 2 Beds
- 2 Baths
- 900 Sq Ft
- Property for Rent
1102 Pearl St, Key West, FL 33040
1102 Pearl St, Key West, FL 33040Total renovation, 2/2 Furnished Pool home, everything but outside walls were replaced, entire ceiling and walls have spray foam insulation, concrete slab floor, open beam ceilings, high quality appliances including the Wolf range, quartz counters, one bedroom, one den that can function as second bedroom, loft has a queen bed, one interior bathroom, one exterior full bathroom, heated pool, IPE
Yvette Talbott Appraisers of the Keys Inc (KW)
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$2,700 per month
- 2 Beds
- 2 Baths
- 884 Sq Ft
- House for Rent
29720 Journeys End Rd, Big Pine Key, FL 33043
29720 Journeys End Rd, Big Pine Key, FL 33043Property Id: 2012413Unfurnished, Spacious stilt home featuring 2 bedrooms and 2 full bathrooms. Enjoy outdoor living on the screened porch—perfect for relaxing or entertaining. Home includes skylights for natural lighting and a storage area beneath the house for added convenience.$8,100 to move in (First, Last and Security) $2700 X 3Monthly Lawn maintenance is
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$10,995 per month
- 4 Beds
- 3 Baths
- 3,116 Sq Ft
- House for Rent
30825 Ortega Ln, Big Pine Key, FL 33043
30825 Ortega Ln, Big Pine Key, FL 33043Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quiet street,just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. This charminghome comes fully furnished and features an open-concept layout, modern updates, and coastal finishes throughout. relax on the coveredporch, entertain on the spacious deck,
Walter Vargas Cervera Real Estate Inc.
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$3,500 per month
- 2 Beds
- 2 Baths
- 700 Sq Ft
- House for Rent
6800 Maloney Ave, Stock Island, FL 33040
6800 Maloney Ave, Stock Island, FL 33040Property Id: 1923697In Harbor Shores. A mobile home community. A nice park with close access to Key West. A cute, quaint, comfortable place to escape the busy life and come sit and enjoy. Water views from back patio deck or relax in front. Surrounded by tropical plants. 2Bd/2bth approx. 700 sq. ft. Furnished. Propane stove, Stackable washer/dryer. Fridge, Microwave, dishwasher. Tile &
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$4,500 per month
- 2 Beds
- 2 Baths
- 1,464 Sq Ft
- Property for Rent
61 W Cahill Ct, Big Pine Key, FL 33043
61 W Cahill Ct, Big Pine Key, FL 33043Long-term canalfront rental on Big Pine Key. Great location for boaters! Primary bedroom with en-suite bathroom on 2nd floor. Add a bed to the office downstairs to create a 2nd bedroom. Furnishings negotiable - home is currently mostly furnished. Screened porch overlooks the 75 ft wide canal with 60 ft of seawall. Fenced yard. Unobstructed sunset views over the wetlands across the street. Plenty
Karen Quist Berkshire Hathaway Home Services Keys Real Estate - Big Pine Key
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$4,900 per month
- 2 Beds
- 1.5 Baths
- 780 Sq Ft
- Townhouse for Rent
113 Golf Club Dr, Key West, FL 33040
113 Golf Club Dr, Key West, FL 33040Pet friendly! Available Oct 1, 2025 for an annual lease at $4,900 a month. 6 month lease option available. Call to discuss 6 month pricing. Located in the Key West Golf Club. Just a few minutes from downtown Key West restaurants and bars. Less than a mile away from boat rental marinas, fishing charters, sand bar and snorkeling tours. Fully furnished rental. Recently painted, new floors, new full
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$5,500 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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$3,200 per month
- 2 Beds
- 2 Baths
- 772 Sq Ft
- Condo for Rent
3655 Seaside Dr Unit 128, Key West, FL 33040
3655 Seaside Dr Unit 128, Key West, FL 330402 bed 2 bath condo located at the "Salt Ponds" condo complex. Convenient to everything Key West has to offer. Enjoy relaxing by the pool, playing tennis, and walking/jogging along the grounds. Restaurants, beaches and down town are easily accessible by bicycle or scooter. Amenities include pool, tennis court, 2 parking spaces -(including 1 covered space). Appliances: Dishwasher, Air Conditioning,
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$5,500 per month
- 3 Beds
- 3 Baths
- 1,240 Sq Ft
- Property for Rent
12 Kingfisher Ln, Key West, FL 33040
12 Kingfisher Ln, Key West, FL 33040Fully furnished, detached 3-bedroom, 2.5-bathroom home in the idyllic Key West Golf Club gated community. Boasting an open floor plan ideal for hosting, the living, dining, and kitchen areas flow gracefully into a screened porch, perfect for relaxation. Upstairs, find all bedrooms, including a master with an ensuite bathroom, while the two guest bedrooms share a full bath. A convenient powder
Hana Tomita Berkshire Hathaway HomeServices Knight & Gardner Realty
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$4,700 per month
- 2 Beds
- 1 Bath
- 744 Sq Ft
- Condo for Rent
1324 Seminary St Unit 1324 Seminary St, Key West, FL 33040
1324 Seminary St Unit 1324 Seminary St, Key West, FL 33040This tastefully updated two-bedroom, one-bath condo in Midtown Key West is available for a yearly rental! Offering a cozy and inviting living space this property features a private pool, spacious outdoor living areas, and beautiful professional landscaping. Enjoy the convenience of two assigned parking spaces, plus additional room for scooters — a rare find in this area. Ideally located less than
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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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$3,500 per month
- 2 Beds
- 2 Baths
- 772 Sq Ft
- Condo for Rent
3655 Seaside Dr Unit 128, Key West, FL 33040
3655 Seaside Dr Unit 128, Key West, FL 330402 bed 2 bath condo located at the "Salt Ponds" condo complex. Convenient to everything Key West has to offer. Enjoy relaxing by the pool, playing tennis, and walking/jogging along the grounds. Restaurants, beaches and down town are easily accessible by bicycle or scooter. Amenities include pool, tennis court, 2 parking spaces -(including 1 covered space). Appliances: Dishwasher, Air Conditioning,
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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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$4,200 per month
- 3 Beds
- 2 Baths
- 1,276 Sq Ft
- House for Rent
1709 Rose St, Key West, FL 33040
1709 Rose St, Key West, FL 33040This quality-built home features solid concrete construction with a durable metal roof. Inside, you'll find a blend of wood and tile flooring, elegant oak doors, granite countertops, and stainless steel appliances including a gas stove perfect for the home chef.The raised ceiling and open-concept design create an ideal space for entertaining, with a stunning dual wall of glass that
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$4,500 per month
- 2 Beds
- 2 Baths
- 948 Sq Ft
- House for Rent
24317 Caribbean Dr W, Summerland Key, FL 33042
24317 Caribbean Dr W, Summerland Key, FL 33042Welcome to Casa Caribe, a long-term rental, comfortable 2 bed, 2 bath vacation home on Summerland Key. Located on one of the best canals on the island, and conveniently across the canal from the Summerland Marina, this home provides quick boating to the blue water as well as the prime diving areas of the Gulf and Looe Key National Marine Sanctuary out front. Large boats will tie up easily at
Mary Conklin Action Keys Realty of the Lower FL Keys LLC
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$3,200 per month
- 2 Beds
- 1 Bath
- 690 Sq Ft
- Condo for Rent
1315 Laird St Unit B, Key West, FL 33040
1315 Laird St Unit B, Key West, FL 330402 Bedroom/1 bath first floor apartment, with living room and eat in kitchen, available near Casa Marina neighborhood. 5 min walk from White Street Pier. Rent is $3,200 and includes water/sewer, a parking space, hookup for washer/dryer, and a shared lot. Pets allowed with a non-refundable $150 fee. Available now
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$14,000 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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$3,500 per month
- 2 Beds
- 1 Bath
- 800 Sq Ft
- House for Rent
6400 2nd St, Key West, FL 33040
6400 2nd St, Key West, FL 33040Corner lot property, AC, fans, yard, car port, wall, gate.
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$3,450 per month
- 1 Bed
- 1 Bath
- 450 Sq Ft
- Property for Rent
623 Whitehead St, Key West, FL 33040
623 Whitehead St, Key West, FL 33040Charming 1-Bedroom Home in Old Town with Bonus Loft Space! Fully renovated 1-bedroom, 1-bathroom rental home in the heart of Old Key West, featuring a bonus loft, one off-street parking space and a washer/dryer inside. Fully furnished, the property includes a cozy sitting room, a well-equipped kitchen, large bedroom, and updated bathroom with new shower. Relax on the porch, surrounded by lush
Damian Vantriglia Berkshire Hathaway HomeServices Knight & Gardner Realty
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$5,500 per month
- 2 Beds
- 2 Baths
- 1,156 Sq Ft
- House for Rent
24 Cactus Dr, Key West, FL 33040
24 Cactus Dr, Key West, FL 33040Tropical Waterfront Paradise - Just Minutes from Key West! This beautifully maintained 2-bedroom, 2-bathroom CBS home sits on a crystal-clear, deepwater canal with 80 feet of concrete seawall and oversized dockage, making it perfect for boating, swimming, and soaking up the Florida Keys lifestyle. Located just 10 minutes by boat from Mallory Square, you can enjoy all the island excitement while
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