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Rentals in Monroe County, FL with 4-Bedrooms

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  • /70

    $12,500 per month

    • 4 Beds
    • 4 Baths
    • 2,952 Sq Ft
    • Property for Rent

    21640 Overseas Hwy, Summerland Key, FL 33042

    Waterfront Paradise in Cudjoe KeyWelcome to 21640 Overseas Highway, Cudjoe Key, FL 33042--a spectacular 4-bedroom, 4-bathroom waterfront sanctuary offering panoramic open-water views and the ultimate Florida Keys lifestyle.Inside, the home features a beautifully updated kitchen with modern finishes, spacious living areas designed for comfort and entertaining, and a huge master suite overlooking

    Agent Photo

    Dan Serban

    Key West Luxury Real Estate Inc (KW)

    (786) 442-3255

    21640 Overseas Hwy, Summerland Key, FL 33042
  • /20

    $5,537 - $15,000 per month

    Little Torch Cottages

    2 - 4 Beds

    28501 Channel View Dr, Little Torch Key, FL 33042

    In Little Torch Key, near Mile Marker 28 on US Highway 1, Little Torch Cottages features 48 homes for those looking for something special. This beautiful property has 400 feet of open water views on Pine Channel, and also offers 22 foot boat slips at a discounted monthly rate for community residents. You will also be able to enjoy a community Clubhouse, park, BBQ areas, Paddle Board and Kayak

    28501 Channel View Dr, Little Torch Key, FL 33042
  • /65

    $8,500 per month

    • 4 Beds
    • 3 Baths
    • 3,116 Sq Ft
    • House for Rent

    30825 Ortega Ln, Big Pine Key, FL 33043

    Welcome to your slice of paradise in Big Pine Key! This stunning property offers peace and privacy on a quietstreet, just minutes from world class fishing, boating, and the natural beauty of Bahia Honda State Park. Thischarming home comes fully furnished and features an open-concept layout, modern updates, and coastal finishesthroughout. relax on the covered porch, entertain on the

    Walter Vargas Cervera Real Estate Inc.

    30825 Ortega Ln, Big Pine Key, FL 33043
  • /20

    $3,839 per month

    • 4 Beds
    • 2 Baths
    • Condo for Rent

    210 W 2nd Ct Unit ID1307150P, Key Largo, FL 33037

    The advertised rate of $3,840/month is the lowest available price, based on a 1 month(s) stay with a move-in date of April 15, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    210 W 2nd Ct Unit ID1307150P, Key Largo, FL 33037
  • /38

    $3,900 per month

    • 4 Beds
    • 2 Baths
    • 1,752 Sq Ft
    • House for Rent

    42 Transylvania Ave, Key Largo, FL 33037

    Annual Rental - Beautiful 4 Bedroom / 2 Bathroom CBS HomeStep into this like‑new, fully furnished 4‑bedroom, 2‑bathroom home--tastefully decorated and completely move‑in ready. Just bring your toothbrush and start enjoying the Florida Keys lifestyle.Large screened‑in patio perfect for relaxing or entertaining in your private fenced in back yard. Plenty of parking for

    Tracey Petrusha Venture Realty Group

    42 Transylvania Ave, Key Largo, FL 33037
  • /83

    $14,666 per month

    • 4 Beds
    • 4.5 Baths
    • 2,594 Sq Ft
    • Condo for Rent

    811 104th St Unit ID1325586P, Marathon, FL 33050

    The advertised rate of $14,667/month is the lowest available price, based on a 1 month(s) stay with a move-in date of September 26, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it

    811 104th St Unit ID1325586P, Marathon, FL 33050
  • /17

    $3,900 per month

    • 4 Beds
    • 2 Baths
    • 1,845 Sq Ft
    • House for Rent

    308 2nd Terrace, Key Largo, FL 33037

    Lovely home ready for your family. Lage 3/2 with media room which can be used for 4th bedroom. Large back screen porch and deck area. Premier family neighborhood. Available March 1st.

    Maryann Warren Coldwell Banker - Ft. Lauderdale

    308 2nd Terrace, Key Largo, FL 33037
  • /20

    $8,109 per month

    • 4 Beds
    • 2 Baths
    • Condo for Rent

    247 Apache St Unit ID1307250P, Tavernier, FL 33070

    The advertised rate of $8,109/month is the lowest available price, based on a 30 day(s) stay with a move-in date of March 23, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    247 Apache St Unit ID1307250P, Tavernier, FL 33070
  • /41

    $7,500 per month

    • 4 Beds
    • 3 Baths
    • 2,581 Sq Ft
    • House for Rent

    103 Starfish Ln, Tavernier, FL 33070

    Awesome view of the Bay from the Chickee Hut Dock to Full Roof Top Patio. 2 story Large Master Bedroom with Steam Shower. Concrete L shaped dock with 15,000 lb lift. There is also a cocktail pool to enjoy after a day out on the water. Ready for your families dream vacation in the Florida Keys. Fantastic Neighbors and Neighborhood. Great water access!! King bed in main bedroom queen beds in the

    George Matter EXP Realty LLC

    103 Starfish Ln, Tavernier, FL 33070
  • /45

    $7,782 per month

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

    1315 Whitehead St Unit ID1297834P, Key West, FL 33040

    The advertised rate of $7,782/month is the lowest available price, based on a 30 day(s) stay with a move-in date of August 5, 2026.Rates vary depending on the duration of stay, season, and other parameters. For exact pricing and additional pricing components, please visit our website and enter your desired move-in and move-out dates. The rate is applicable when billed upfront; it can be

    1315 Whitehead St Unit ID1297834P, Key West, FL 33040
  • /81

    $8,500 per month

    • 4 Beds
    • 4.5 Baths
    • 1 Sq Ft
    • House for Rent

    150 Azalea St, Tavernier, FL 33070

    6+ Month/Annual-- Rental--Beautiful Double Waterfront Lot in Prestigious Plantation Key Colony. This stunning 4-bedroom, 2-bath waterfront home sits on a Rare Double Lot with a Private Boat Ramp & Boat lift. Step outside to your Private Oasis complete with a Private Tiki hut - Gorgeous secluded in-ground Pool and Cabana Hut Bungalow - The open-concept kitchen features Granite countertops and

    Tracey Petrusha Venture Realty Group

    150 Azalea St, Tavernier, FL 33070
  • /2

    $7,000 per month

    • 4 Beds
    • 2 Baths
    • 1,900 Sq Ft
    • House for Rent

    1330 3rd St, Key West, FL 33040

    Property Id: 2292938Move-in ready Key West living! Close to shopping, schools, beaches and Old Town.Property Highlights•Spacious 4 bedrooms / 2 bathrooms•~1,900 sq ft•Fenced yard with covered porch•Pet-friendly with deposit•Annual lease - $7,000 per month•Utilities not included•Credit/Background Check This home combines comfort, space, and

    1330 3rd St, Key West, FL 33040
  • /44

    $10,000 per month

    • 4 Beds
    • 3 Baths
    • 2,058 Sq Ft
    • Property for Rent

    717 Southard St, Key West, FL 33040

    Meticulously renovated 1866 Conch Revival perched atop Solaris Hill in the heart of Old Town and Steps from Old Town's vibrant culture, dining, and entertainment. This historic gem blends rich heritage with contemporary comforts offering an open Floor plan, 2 primary bedroom options (one on first level), cocktail pool, hammock porch and more! Step into the foyer at the corner of Southard & Love,

    Kimberley Haley Brenda Donnelly Real Estate LLC

    717 Southard St, Key West, FL 33040
  • /25

    $10,000 per month

    • 4 Beds
    • 2 Baths
    • 1,575 Sq Ft
    • House for Rent

    125 Gardenia St, Tavernier, FL 33070

    Experience luxury waterfront living in the heart of the Florida Keys! 4 bedrooms and 2 bathrooms. This stunning modern home offers sleek finishes, breathtaking canal views, and direct boating access. Enjoy the spacious outdoor entertainment area, complete with a private dock, lush synthetic turf, and a large jacuzzi—perfect for relaxing under the stars. The upper-level terrace provides an ideal

    Dahiana Rojas de Rojas Canvas Real Estate

    125 Gardenia St, Tavernier, FL 33070
  • /75

    $7,500 per month

    • 4 Beds
    • 5 Baths
    • 2,432 Sq Ft
    • House for Rent

    1516 Aqueduct Ln Unit 1, Key Largo, FL 33037

    Discover coastal living at its finest! This exceptional 4-bed, 3.2-bath canal-front home right next to Adams cut offers over 2,400 sq ft of beautifully designed living space with stunning bay views from wrap-around balconies and a rooftop terrace. Thoughtfully appointed with an elevator, indoor and outdoor kitchens, laundry room, and spacious layouts, this residence is ideal for entertaining and

    Kristal Rivera Diaz LPT Realty, LLC

    1516 Aqueduct Ln Unit 1, Key Largo, FL 33037
  • /33

    $2,950 per month

    • 4 Beds
    • 2 Baths
    • 1,998 Sq Ft
    • House for Rent

    235 Anne Bonny Dr, Key Largo, FL 33037

    Prime Pirates Cove waterfront living! Two private 2BR/1BA homes under one roof, each with full kitchen, washer/dryer, and screened patio. Three properties from open bay with stunning water views. Features include a 50-foot concrete dock, boat launch nearby, and a spectacular 1,000 sq. ft. rooftop deck perfect for entertaining or relaxing with panoramic vistas. Divided outdoor spaces give each

    Milena Wood Barrios and Associates Realty

    235 Anne Bonny Dr, Key Largo, FL 33037
  • /68

    $7,500 per month

    • 4 Beds
    • 5 Baths
    • 2,432 Sq Ft
    • House for Rent

    1516 Aqueduct Ln, Key Largo, FL 33037

    Discover coastal living at its finest! This exceptional 4-bed, 3.2-bath canal-front home right next to Adams cut offers over 2,400 sq ft of beautifully designed living space with stunning bay views from wrap-around balconies and a rooftop terrace. Thoughtfully appointed with an elevator, indoor and outdoor kitchens, laundry room, and spacious layouts, this residence is ideal for entertaining and

    Kristal Rivera Diaz LPT Realty, LLC

    1516 Aqueduct Ln, Key Largo, FL 33037
  • /83

    $18,000 per month

    • 4 Beds
    • 4 Baths
    • 2,300 Sq Ft
    • House for Rent

    96180 Overseas Hwy Unit 1, Key Largo, FL 33037

    UNIQUE KEY LARGO WATERFRONT ESTATE | PRIVATE SANDY BEACH + DOCK | 4BD/4BA | POOL | ~0.90 ACREWelcome to your own slice of the Keys—an exceptional waterfront retreat in Key Largo featuring a private sandy beach, dock, and resort-style outdoor living on approximately 0.90 acres. Designed for effortless coastal living and entertaining, this home offers 4 bedrooms and 4 bathrooms with seamless

    Alex Lipzer Key Biscayne Realty Group, Inc

    96180 Overseas Hwy Unit 1, Key Largo, FL 33037
  • /38

    $5,500 per month

    • 4 Beds
    • 3 Baths
    • House for Rent

    251 Pueblo St, Tavernier, FL 33070

    Located in the desirable Indian Waterways neighborhood on Plantation Key. Canal-front home with private dockage and a layout well suited for comfortable long-term living in the Florida Keys. The main living area is on the second level and features an open, light-filled floor plan with large windows and vibrant coastal decor. The primary bedroom includes a queen bed, an ensuite bath, and access to

    Jocelyn Marzella Ocean Sotheby's International Realty

    251 Pueblo St, Tavernier, FL 33070
  • /37

    $15,000 per month

    • 4 Beds
    • 2 Baths
    • 2,000 Sq Ft
    • House for Rent

    309 Calzada de Bougainvillea, Marathon, FL 33050

    4/2 renovated furnished home steps from Sombrero Beach. features pool with new heater/chiller, a private boat dock with new Power Pedestal, a fish cleaning station with water & accommodates up to 50 ft vessels. With only minutes from the Atlantic and steps to the Beach, this is an ideal location. The Light & bright kitchen has been completely remodeled and boasts new state of the art Cafe

    Thania Moses Zeff Realty LLC,

    309 Calzada de Bougainvillea, Marathon, FL 33050
  • /27

    $35,000 per month

    • 4 Beds
    • 4.5 Baths
    • 5,348 Sq Ft
    • House for Rent

    133 Severino Dr, Islamorada, FL 33036

    Experience luxury living at its finest in this completely renovated four-bedroom, four-bathroom home nestled in one of the most prestigious neighborhoods in the upper Keys. This stunning residence showcases exceptional craftsmanship by a renowned local builder, creating an extraordinary retreat where sophisticated design meets tropical paradise. The home features two separate living areas and

    Pete Riveiro The Firm Realty Group

    133 Severino Dr, Islamorada, FL 33036
  • /26

    $3,995 per month

    • 4 Beds
    • 2 Baths
    • 1,344 Sq Ft
    • Property for Rent

    164 Blue Harbor Dr, Tavernier, FL 33070

    PERFECT VACATION HOME! Available Immediately Beautiful & Spacious 4 Bedrooms & 2 Bathrooms POOL HOME with a wraparound porch & Pool Cabana & outdoor kitchen located in Blue Harbor Private Community Home is located Right across from the Boat Ramp Property offers plenty of space for a Big Family to enjoy endless days of fishing and water activities Space for boat and other water crafts, home is

    Ernie Echauri RE/MAX All Keys Real Estate

    164 Blue Harbor Dr, Tavernier, FL 33070
  • /66

    $3,400 per month

    • 4 Beds
    • 3 Baths
    • 1,944 Sq Ft
    • Property for Rent

    945 Plantation Rd, Key Largo, FL 33037

    Beautifully decorated Key Largo rental! Spacious 4 bed, 3 bath manufactured home featuring two primary suites, wood floors, washer/dryer room, and an open layout with multiple living areas. The kitchen offers stainless steel appliances, an eat-in area, and separate dining room. Enjoy a cozy sitting room, nautical décor, and plenty of space for a large family. Outdoor living includes an open patio

    Rogelio Lucas Stratwell, LLC

    945 Plantation Rd, Key Largo, FL 33037
  • /46

    $5,500 per month

    • 4 Beds
    • 4 Baths
    • 1,618 Sq Ft
    • House for Rent

    903 Tropical Ln, Key Largo, FL 33037

    Welcome to your Key Largo escape! This beautifully updated 4 bedroom, 4 bathroom two story home offers the perfect balance of comfort and coastal lifestyle with 1618 sq ft of living space. Nestled on the Bayside with direct canal access, the property features a 40 foot wood dock-ideal for boating, fishing, or simply enjoying the water. Whether you're bringing your boat or just soaking the

    Robert Valenzuela Century 21 Circle- Islamorada

    903 Tropical Ln, Key Largo, FL 33037
  • /11

    $4,500 per month

    • 4 Beds
    • 2 Baths
    • 1,620 Sq Ft
    • House for Rent

    350 Hazel St, Key Largo, FL 33037

    For more information call the listing agent.

    Edith Diaz Next House Realty

    350 Hazel St, Key Largo, FL 33037
  • /37

    $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
  • /58

    $15,000 per month

    • 4 Beds
    • 4 Baths
    • 3,083 Sq Ft
    • House for Rent

    3 North Dr, Key Largo, FL 33037

    SEASONAL .This 4 bed 4 baths Key West style pool . Price depends of the season . Once inside take the stairs up to the main living area where you will find two bedrooms and two baths ,living room and eat in kitchen with wet bar fully equipped laundry room , large screened patio for dining with TV, back yard with large heated pool with lounge sitting area ,tropical landscaping, Dock will

    Arturo Rodriguez Coldwell Banker Realty

    3 North Dr, Key Largo, FL 33037
  • /9

    $12,500 per month

    • 4 Beds
    • 3 Baths
    • 2,855 Sq Ft
    • House for Rent

    28502 Channel View Dr, Little Torch Key, FL 33042

    This is a 3 story furnished 4 bedroom 3 bathroom home with a water view of the gulf in the Little Torch Cottages community of townhomes. There are 2 heated and chilled community pools, a gym, a sauna, a marina with boat ramp, bbq, exterior yard games and boat slip available for an extra charge. Kayaks and paddle boards are available for community usage.

    Joseph Danieli AKT Realty LLC

    28502 Channel View Dr, Little Torch Key, FL 33042
  • /51

    $18,000 per month

    • 4 Beds
    • 3.5 Baths
    • 4,500 Sq Ft
    • House for Rent

    124 S Indies Dr, Marathon, FL 33050

    28-day minimum rental. Welcome to paradise! This luxury 4,700+ SF custom home is just 1,100 ft from the ocean inlet with no fixed bridges, 100' wide canal, and ocean views from the 3rd-story loft. Includes two 25K lb boat lifts (up to 40' boats), double jet ski lift, paddle boards, fishing rods, golf carts, and more. Kid-friendly with 6 bunk beds—sleeps 16+. Features hurricane impact windows,

    John DeMarco RE/MAX 5 Star Realty

    124 S Indies Dr, Marathon, FL 33050
  • /41

    $12,000 per month

    • 4 Beds
    • 2 Baths
    • 1,680 Sq Ft
    • House for Rent

    203 Atlantic Blvd, Key Largo, FL 33037

    BEAUTIFUL HOME!.. accommodating 10 guests, your perfect vacation, prestigious community of Port Largo. Upstairs you will find 2 bedrooms and a full bath each with a queen bed. Downstairs has 2 bedrooms with 2 twin beds in each room and a full bath. Both floors also have a sofa bed, floors do not connect through indoor staircase. Offering a private 75 foot dock for boats and direct access to the

    Aymee Pita Capital Homes Inc

    203 Atlantic Blvd, Key Largo, FL 33037
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